Wikipedia talk:WikiProject Chemicals/Archive 2005

This page contains archive discussion about the wikipedia:WikiProject Chemicals for 2005

Contributions

I would like to participate in this work. I am a chemistry professor working in the US. My area of speciality is in organic chemistry, though I also use a lot of inorganics, particularly lanthanides, in my research. I recently began making contributions to Wikipedia, for example cerium(III) chloride.

I would suggest that we look at developing a standard format for pages on chemical compounds (the chemical elements already look very nice!). This may need some variation- for example something common like methanol has data such as triple point, whereas something more complex like morphine will not. In addition, I would suggest that we have one format for inorganic compounds and another for organics.

I would also suggest that we tighten up on naming. I have noticed that for inorganics some metal compounds are named like copper(II) chloride (this follows the IUPAC and ACS rules), while others are named like copper (II) chloride (with a space after the metal- this is not an official naming convention as far as I know). I think we should standardise all names to the IUPAC/ACS system, which is what I understand Wikipedia is aiming to do.

I want to get the discussion started and get people's thoughts on what should be done. Also, could someone tell me how I can sign up as a participant- as a newbie, am I eligible to do this? I refrained from editing the page to do this, because of the warning at the top of the page!

Thanks, Martin A. Walker Walkerma

Welcome! These are good ideas. With your experience, you're better suited than I am to decide what this project should accomplish, so you needn't be concerned by the warning. --[[User:Eequor|ᓛᖁᑐ]] 22:52, 30 Nov 2004 (UTC)

I tend to enjoy working on articles about rather obscure things, and a lot of chemical compounds fall into this category. However, for many of these compounds, I don't have access to a lot of information. I would be willing to contribute a bit here and a bit there, adding the information I have available, but I won't necessarily be able to provide full coverage on a lot of these compounds.

I added an infobox for acenaphthylene, but it's mostly question marks at this point. Are there any comments or suggestions before I do this kind of thing for more compounds? —Bkell 06:37, 23 Jan 2005 (UTC)

I have an office full of reference books- I also have a personal collection of 30-40 years of several journals, as well as access to a decent college library. I don't always have time to do every little thing, but if you can get some stubs started, I can probably fill in a lot of the blank spaces and ?s when I get a few minutes free. So please start some, we'd really appreciate it! Can you just let us know the pages you have submitted?

By the way, you can get a lot from the NIST website if you want physical data. For example, for acenaphthylene, I found this when I asked for IR and condensed phase data. I confess, I never use such data (other than IR) myself, so the pages I write myself tend to focus on more applied data you would need to use it routinely in the lab (see cobalt(II) chloride as an example). Walkerma 01:40, 24 Jan 2005 (UTC)

Request

Hi, here are some requests for your project (i'm not a chemist, or would offer to contribute)

• IUPAC/ACS system, a simple naming tutorial for us mere mortals
• polymer acroynm naming systm, is there such a thing? (see Fluoropolymer Thermoplastic)

Duk 19:14, 1 Dec 2004 (UTC)

Thanks for the input- we must address this when we choose a template. There are already a couple of pages on naming. The inorganic naming still needs some work, though there is one page that is a good start- see Systematic name. There is an excellent page for organic compounds naming at IUPAC nomenclature which is a fabulous resource for those learning organic chemistry- even "mere mortals". What seems to be really lacking is good linking to these pages- so we need to ensure that any templates we use include links on this. After only two months on Wikipedia, I've seen this problem already, see Talk:Silver(I) fluoride.

As for polymers, that is another whole field, one which I know very little about- I only know the common acronyms. Since polymers are commercially VERY important, we need to have something on this. We do have Category:Organic polymers, and a few acronyms show up there and on List of compounds (look under the "P"s particularly). I may start something off on acronyms, but it'll be pretty basic! Walkerma 22:29, 3 Dec 2004 (UTC)

OK, from Viton, Viton® fluoroelastomers are categorized under the ASTM D1418 & ISO 1629 designation of FKM. and from [1], Establishes a system of symbols for the basic rubbers in both dry and latex forms, based on the chemical composition of the polymer chain. Standardizes the terms used in industry and commerce . If someone has access to these standards it would sure be usefull page, Polymer acronyms or something like that. -- Duk 17:48, 1 Mar 2005 (UTC)

See also List of ISO standards. --Duk 17:58, 1 Mar 2005 (UTC)

IUPAC names for inorganics

There seems to be total confusion out there on how to name inorganic compounds! To help resolve this I went rummaging in my basement and dug out the relevant journal (JACS, 82, 5525 (1960)), the most relevant pages are now scanned in at http://www2.potsdam.edu/walkerma/inorg_naming.pdf This is the original set of rules, I am ordering a book on the latest revisions, but my understanding is that these rules are by-and-large still current. When there are variable or non-obvious oxidation states, the basics are:

• Metal compounds are named using the Stock system. The article indicates that Greek prefixes are also possible, but that approach is considered obsolete (read any introductory chemistry textbook to see this). The preferred (Stock) involves using Roman numerals in parentheses IMMEDIATELY AFTER the element name to indicate oxidation number. Example from the article: FeCl₂ iron(II) chloride
• Nonmetal compounds are to be named using Greek numerical prefixes. The prefix mono may generally be omitted. Example from the article: NO₂ nitrogen dioxide.

I will try to work on correcting material on naming already on Wikipedia, since this will become a primary reference for us.

I would like to propose that one of our first tasks should be to get all existing compounds pages to conform to the above rules. Any comments? Walkerma 22:45, 6 Dec 2004 (UTC)

Thank you for letting me know this. I stand corrected: I'll use the IUPAC style from now on. We probably need to reference this information in the Wikipedia Manual of Style, since it is different to normal English-language style for parentheses. -- The Anome 08:30, Dec 7, 2004 (UTC)

Navigational aids for chemical compounds

I think alphabetical listings are not always the best way to classify chemical compounds. For example, what if you want to find out all of the compounds of aluminium that have pages? Or if you want to know what pages there are for organics containing four carbons, or of formula C₄H₁₀O? To begin addressing this I have begun writing a page Inorganic compounds by element which deals with the first problem. I thought long and hard, and researched some chem catalogues to try and pick out what I believe to be a pretty complete list of IMPORTANT compounds of those elements. I have tabulated them and used formulae, in order to keep it extremely concise. In my opinion, one problem with List of compounds is that it is full of obscure compounds that no one is ever going to write a page on. Another problem with list of compounds is that it only has one compound per line, so you have to scroll down a lot to find things.

Another nice thing about Inorganic compounds by element is that we can give a direct link from (for example) the aluminium page to Inorganic_compounds_by_element#Aluminium, this would be very useful.

I think we should also have an organics page listed by chemical formula (Hill formula order- C, then H, then others alphabetically) which would address the organics queries mentioned. Comments, anyone? Walkerma 19:38, 1 Mar 2005 (UTC)

Lists on /organization page

These lists are coming along nicely and should be pretty much ready soon. My view is that

• We shouldn't write in "wish lists" of compounds without pages, beyond the number needed to meet the goal. However it is OK to put (for example) two compounds for an element in the inorganics list, if both articles are complete or close to complete.
• We should not put minerals or mixtures in. These rarely have much chemical information beyond a basic formula or two. These were a headache when I was going through List of compounds.
• We need to have some indicator as to whether the linked page meets our goal or not. As for myself, I have done this rather crudely by adding comments after incomplete entries, such as (Needs table + content). Perhaps we could put links in bold for articles that we consider "complete"?
• In order to fill out some lists where we clearly have blank spaces, I have put suggestions in plain text (except in the case of the inorganics, where the elements are fixed!). If you come up with better suggestions, or you find near-complete pages that I or others missed, put these in instead.
• Once the lists are done- who is going to actually write the missing pages or upgrade the poor ones?! We'll have to come up with a monthly action list, with participants agreeing what they would like to work on.

Please comment or add your suggestions. Walkerma 07:56, 13 Apr 2005 (UTC)

• Agree.
• Agree.
• I'll work on a nice image thing, for putting there. That's nicer.
• Us. I don't think we should make a strong timetable, just a list of what is to be done. That will let all the people to choose their own speed of working on things. But I agree we should have a good indication of what is done or not.

Perhaps we should indicated per section what the specific requirement for the articles are, e.g., which infobox to use, and which things are minimal (references?). And are the infoboxes final enough to be ready for real use? I have a question open there about linking back to the chem infobox wikipage. Wim van Dorst 20:52, 2005 Apr 13 (UTC).

I don't think there is anything wrong with a wish list of compounds in the various categories. Their presence on the wish list could be a subject of debate - that's why we have such a "openly available" list. The number of compounds in each category is somewhat arbitrary anyway. You can take note of what I did to the polymers list. Certain polymers were obviously important enough to be included in the list - these weere numbered and listed first. After that more questionable candidates were added unnumbered to the list as "maybe's" below a certain line. Maybe we can have a rating system for the importance of each compound. H Padleckas 15:25, 2 May 2005 (UTC)

Methylsulfonylmethane

This article REALLY bothers me on so many levels. Not only should it be named "Dimethyl sulfone", but most of the info in it is quackery. I would like to edit this article, adding more chemistry information. However, I feel I may be entering a battlezone. Can you give me advice as to how I (or we) should proceed? ~K 03:45, 1 May 2005 (UTC)

The MSM article indeed has been the field of rather hefty discussions, but for several months it is rather quiet there (see the history). The attention of Ta bu shi etc (actually a big fish in Wikipedia, contradicting his username) has helped to tone down the various discussions. So, I would suggest that you simply start a whole new page with the proper name Dimethylsulfone, add good info and facts, follow the Chemicals Wikiproject suggestions (infoboxes, IUPAC naming, etc), and let all serious contributors add to that page. The slogan of Wikipedia is Be Bold but at the same time is the slogan of people who have sympathy for their environment Tread Lightly. Wim van Dorst 12:50, 2005 May 2 (UTC).

A lot of nutritional supplement vendors and authors call this compound Methylsulfonylmethane or MSM. This name seems clumsy to me in view of the fact that it can be called dimethylsulfone, but the name is used widely. I think we can start working on Dimethylsulfone leaving the Methylsulfonylmethane as it is for now, to be merged later on. I would not separate "dimethyl" and "sulfone" in the name with a space. H Padleckas 15:07, 2 May 2005 (UTC)

I didn't put such a non-IUPAC space in there, did I ;-). Wim van Dorst 15:58, 2005 May 2 (UTC).

I agree that the article should be renamed "dimethyl sulfone", as that is the correct chemical name. The page "methylsulfonylmethane" or "MSM" should simply redirect to the dimethyl sulfone page. As far as entering a battlezone, I would just echo the advice given above: tread lightly. For example, labeling something as quackery sets up a combative tone. Please make sure you consider all of references which are supplied before condemning what you have read on the "MSM" page. Most of the claims made about dimethyl sulfone in the article have been validated by research published in peer-reviewed journals. Where that is not the case, I have made an effort to say so (i.e., MSM has been purported..."). Your contribution is appreciated, but inappropriate dismissal is as bad as overstating the case. If you have questions or challenges to anything written, feel free to contact me, as I wrote the lion's share of the original article. I have tried to make it objective. If you feel it is not, you are welcome to question specific assertions.--Naturodoc 19:40, 29 July 2005 (UTC)

Phosphorus chlorides

I started an article called Phosphorus chlorides. Phosphorus trichloride, phosphorus pentachloride, and diphosphorus tetrachloride are 3 chlorides mentioned in there. I inserted references to these in Chloride, Hydrogen chloride, and in Acyl chlorides in a new preparation section. Also the Benzoyl chloride stub mentions PCl₅. The article has been expanded slightly and molecular images were added. Since then User:Walkerma has written articles on Phosphorus trichloride and Phosphorus trifluoride, in addition to the previous article on Phosphorus tribromide. It is not clear what will be done about the other phosphorus chlorides.
H Padleckas 16:20, 18 Apr - 2 May 2005 (UTC)

This was a case of two people working on similar topics at the same time! As I see it, the question regarding this page is:

1. Should we expand the Phosphorus chlorides page to include POCl₃ and PSCl₃, and similar?
2. Or should we rename the page Phosphorus halides and make it a much broader page?

I expect someone will write a specific PCl₅ page within the next few months, as it's a pretty important compound, and the same is probably true for POCl₃.Walkerma 18:01, 3 May 2005 (UTC)

If I would have known how technical Phosphorus trifluoride would have turned out and that it had no bulk industrial applications, I would have recommended that just a brief summary be included in a Phosphorus halides article. But it's already written; let's enjoy it. H Padleckas 06:57, 7 May 2005 (UTC)

Does this mean you think we should broaden the phosphorus chlorides page to become halides, or not? Do we include oxyhalides? Are you going to write the first draft or do you want me to? Walkerma 16:34, 7 May 2005 (UTC)

I suggest expanding phosphorus chlorides to phosphorus halides, otherwise we will eventually have problems with bromides, oxyfluorides etc. on other phosphorus compound pages. There is a beer in Arras (Northern France) for the person who knows the problems posed by the industrial use of phosphorus trifluoride - votes to User Talk:Physchim62. Physchim62 15:19, 8 May 2005 (UTC)

Article considered for deletion

I noticed this amino acid article listed on Wikipedia:Votes for deletion: 3,4-Methano-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid. If you know anything about it (or are willing to learn ;-), please cast your vote. Wipe 12:24, 3 May 2005 (UTC)

This article has been deleted based on strong Delete recommendations. H Padleckas 08:51, 27 May 2005 (UTC)

For future reference, the complete discussion can be found here: Wikipedia:Votes for deletion/3,4-Methano-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid. Wipe 15:16, 27 May 2005 (UTC)

Please see Talk:Cyanuric acid

Please see Talk:Cyanuric acid and see if you know the answer to the question posed there?
H Padleckas 06:43, 7 May 2005 (UTC)

New chembox

For those who don't watch Wikipedia:Chemical_infobox, we are working on a major revision of the standard template for the properties table. Please take a look at the draft version of the new table and leave comments here. The earlier discussion mainly occurs here. Walkerma 03:54, 11 May 2005 (UTC)

The development of the new chembox is in its final stadium. Please be informed that full discussion is going on at the above links, and the forthcoming version (draft till tomorrow) is visible there too. Everybody is strongly invited to contribute now. Wim van Dorst 12:56, 2005 May 16 (UTC).

The new version of the full chembox has now been posted. Walkerma 18:05, 16 May 2005 (UTC)

Familiar names vs. IUPAC names

Here's something to consider: the normal naming convention for article titles is that the title should be the most commonly used name for the article's topic, with the correct name, if different, being mentioned as soon as possible in the article. We need to work out how we reconcile this with moving towards IUPAC names as standard within articles. -- The Anome 08:36, Dec 7, 2004 (UTC)

I agree with you, and this is one issue that will never go away! I do not advocate using IUPAC for everything. The Wikipedia Manual of Style states, "In articles about chemicals and chemistry, use the style of the International Union of Pure and Applied Chemistry (IUPAC) for chemical names wherever possible, except in article titles, where the common name should be used if different, followed by mention of the IUPAC name". Clearly the name of water should not be changed to IUPAC, and I would agree that if a chemical has a common name in widespread use this should be the principal name. The only case I can see where this as a problem is where you have another important use of the same word, for example "ether" for diethyl ether (aka ethyl ether), where to a chemist in means any ROR' compound.

The other (more serious) issue is to define what is common. There are huge differences between different parts of the world (I am a Brit living in the US so I see this a lot!): For example poly(ethene) (IUPAC?? I'm not a polymer chemist!) is known in the US as polyethylene, but in the UK it is always called by the ICI tradename (they invented it), polythene. The other aspect is between disciplines: For example an inorganic chemist will tend to use the "correct" name for SmI₂, samarium(II) iodide, but since this reagent has become popular with organic chemists, you will often see organic papers where it is referred to by a pseudo-organic name, samarium diiodide. That's just within chemistry! When you consider usage of chemicals in other diverse fields such as geology, physics, biology, etc., there are names used that I (as a chemist) had never heard of (such as Blue_stone for copper(II) sulfate).

Fortunately the redirect command can deal with the worst effects of this problem- I don't really care if I find methylene chloride listed as dichloromethane, as long as there is a redirect to help me find the page. Walkerma 17:34, 8 Dec 2004 (UTC)

The following "WikiProject Science" page/link: Wikipedia:WikiProject Science#IUPAC Standard says on this matter:

"In the interest of consistency and clarity the IUPAC standard should be used for chemical names in all science articles."

Just information for your consideration. H Padleckas 11:00, 24 May 2005 (UTC)

We also have Wikipedia:Naming conventions (chemistry) to compare this with! As if that wasn't enough IUPAC allows various options- thus acetone could be called acetone, propanone, propan-2-one or 2-propanone, and all of these are IUPAC (as far as I know, please correct me!). I think we need to find the common sense middle ground, and certainly consider common usage, but we should strongly favour the IUPAC name if it is used. I recently did a request move after some unknown user decided to cut&paste the acetone page over to propanone, and acetone became a redirect until I had it reset (see Talk:Acetone). I turned sulfuric(VI) acid into a redirect, yet I also moved ferric chloride to iron(III) chloride. I recently wrote a new page called vanadium(V) oxide, yet "next door" to that we have another page called titanium dioxide. If we write a style guide, we will have to hammer out exactly how we (as the chemistry community on Wikipedia) believe things should be named- it's not cut & dried. We need to make sure that the rules we propose are as clear as possible, to ensure that we don't have more incidents like the acetone move. Walkerma 22:05, 24 May 2005 (UTC)

Chemical formula images

Chemical structure of ethylene glycol

I have recently started to upload all new images of chemical structures to the Wikimedia Commons. This way it is possible to use the structures in all different wikipedia projects. I upload high resolution, black/white PNG images. These are of surprisingly small file size (the ethylene glycol image to the right has a size of only 3,198 byte at a resolution of 1372 x 469 pixels). Because of the high resolution they can be rescaled dynamically to any size on wikipedia. Additionally, they can be used for printing and projection without pixel artifacts.

Linking is exactly the same as if the images were upladed to en.wikipedia:

[[Image:Ethylene glycol chemical structure.png|thumb|150px|Chemical structure of ethylene glycol]]

The category [[Category:Chemical structures]] is a Wikimedia Commons category for all chemical structures there.

How to draw and upload a chemical structure

This is the procedure I currently use for my images:

ChemDraw molecule editor settings:

• Line width: 0.107 cm
• Bond length: 2.566 cm
• Font: Arial 45 pt
• Save as: TIFF black/white bitmap.

Image processing (Photoshop or Irfan view):

• Add canvas of 75 pixels to all four sides (Photoshop: Image:Canvas Size, relative, 150 pixels width, 150 pixels height)
• Save as a PNG black/white bitmap.

Wikimedia Commons:

• Upload under http://commons.wikimedia.org/wiki/Special:Upload (bookmark address)
• Paste the summary template from below.
• Add the substance's article link to en.wikipedia, the user name, and the date.

Linking:

• As if it were uploaded to en.wikipedia.
• Add the horizontal image size "|200px|" (no frame) or "|thumb|200px|" (frame) to the image link:

[[Image:Ethylene glycol chemical structure.png|thumb|150px|Chemical structure of ethylene glycol]]

Wikimedia Commons summary template:

---

* Description: Chemical structure of [[w:|]].

* Author, date of creation: selfmade by [[w:User_talk:|]], 11 April 2005.

* Source: -

* Copyright: [[w:GNU Free Documentation License|GNU Free Documentation License]]. (GFDL)

* Comments: high-resolution b/w PNG; ChemDraw / Photoshop.

{{GFDL}}

[[Category:Chemical structures]]

---

Cacycle 15:11, 11 Apr 2005 (UTC)

Assessing articles for completeness & coordinating this

I think we need to have some means of tracking our progress towards the goals. The Wikipedia:WikiProject_Chemicals/Organization work-list page is clearly the centre of this, but at present we can only see a blue or red link, unless comments have been added. We need to be able to tell whether something is a short stub, a fairly complete article that needs a little work, or something that is "complete". To that end I have put up a system for article assessment system at Wikipedia:WikiProject_Chemicals/Assessment, and the letters range from F (should be deleted) through E (short stub) to A (Done!).

A necessary part of this system would be people to actually perform the assessments. I propose that each one of the sections of our detailed progress on goal lists should have a coordinator who is responsible for that list. They would perform a regular (is monthly too often? Every three months?) check on each one of the pages in their list, and give a quick assessment. For example "Joe" might go through the inorganics list, while Fred does the polymers. If it gets too much, maybe two people can share the responsibility, doing the assessment every other time. The letter could be entered in just after the Wikilink. Once every entry has an A next to it we can say that the goal has been reached. I will give my assessments for the inorganics section (soon) so that people can get a sense of what I mean. I will not assess articles written mainly by me.

One natural cause for concern is if (say) I write an article that I think is great and at the "A" level, then the coordinator gives it a "B" and my feelings are hurt. Are we all grown up enough to handle this?! As explained on the Assessment page it needs to be understood that everyone will have a different view of what is the perfect article, and that's why I think we need a single coordinator for each list. Presumably if anyone does get offended, the coordinator can either perform an edit or be able to say, "We need to have a section on how it is prepared, and perhaps one or two more references." Speaking personally, I have a great deal of respect for the regular contributors to this project.

I think one strict rule should be, however, that the first version of an article should always be independently assessed- if written by the coordinator then it should initially be assessed by someone else. Thereafter the coordinator can assess the progress of that page.

Is this getting way too "overorganised" for a Wikipedia group? The problem is (IMHO) that we have to be able to monitor our progress, and at present it's hard to tell whether our 50 reagent articles include 45 stubs and 5 good articles, or 45 good articles and 5 that need a bit of work. There is also no one person who is systematically assessing them at regular intervals. I think section coordinators are probably a good idea- they can take the lead on things like template changes, goal changes, nominations for featured article, etc.

If people like this idea then I will probably try recruiting coordinators by leaving messages on personal talk pages. Please give comments on this idea after you have looked at the guidelines. Walkerma 22:59, 29 Apr 2005 (UTC)

I took the liberty of assigning some grades to the list of inorganics, so you can see how it would work. It took me one minute per entry to assess the page and tag the entry. I didn't assess pages that I had a lot to do with. Walkerma 21:08, 30 Apr 2005 (UTC)

List of compounds

The three-way split of this important list is almost complete, and I have set a date of May 31st for the end of this page as a list. After that, users will be advised to visit one of the three parts of the list, namely List of inorganic compounds, List of organic compounds, or List of biomolecules. I added a note at the top of the page. At this point the only work left to do is to pull out any biomolecules from the organics list that don't belong there, and to make sure that the biomolecules list is as complete as it should be. So far I have done this up to end of the letter C. Walkerma 18:22, 21 Apr 2005 (UTC)

• It is done. Good move! And well executed. As the move has now been made, I edited the wikiproject page to reflect the new status of the lists. Do I understand right that we can't move the target to 'finalized' yet? Wim van Dorst 21:25, 2005 Jun 1 (UTC).

New target: 50 biochemicals

I think it was a good idea for Physchim62 to separate out the Biochemicals from the Other (miscellaneous) Compounds List on the Wikipedia:WikiProject Chemicals/Organization page.
H Padleckas 02:57, 1 Jun 2005 (UTC)

Absolutely! Thanks, PC. Walkerma 18:19, 1 Jun 2005 (UTC)

Yep, mee2. I also edited the target in the formal project wikipage. Wim van Dorst 21:01, 2005 Jun 1 (UTC).

How shall we show benzene rings?

Here is a question for all organic chemists; and biochemist, and chemists and chemical engineers in general and others interested in organic chemistry: Shown below are two pictures of the structure of m-chloroperoxybenzoic acid, a chemical reagent sometimes used in organic reactions. Should we standardize the way 6-carbon or 6-atom benzene rings are shown in aromatic compound chemical structures? Should we show them with alternating double and single bonds as shown on the left or with a circle inside the hexagon as shown on the right? Should we just accept both ways as ok, to be decided by whoever creates the picture? Some books show it one way; other books show it the other way. H Padleckas 11:52, 19 May 2005 (UTC)

There are many similar issues in drawing chemical structures: implicit carbon atoms, implicit hydrogen atoms, and common abbreviations (such as Me for CH3). Transition state structures are even more complex. I believe that since there is no standard in industry or academia as to chemical structures, to impose one here on the Wikipedia would be foolish. It would be difficult to form a standard, and be even harder to enforce.

I believe a better solution would be to create a page discussing the various ways chemical structures are drawn. I searched for such a page, and didn't find one. (However, if anyone can find one, please post it here.) ~K 15:22, 19 May 2005 (UTC)

Regarding the specific question, the Kekule form (left hand pic) seems to have become the dominant form- I have a shelf full of new organic textbooks, and they all favour this form. The "ring" structure was fashionable when I was an undergrad, but seems to have fallen out of favour, unless one is drawing something like dibenzenechromium(0). As for K's suggestion of the page, that seems an excellent idea. It should probably be a page associated with this project, and it should include the section from above on #Chemical_formula_images. Walkerma 17:26, 19 May 2005 (UTC)

I agree with all above comments, thereby invalidating my application to join the Association of Pedantic Wikipedians. IMME Kekulé structures are almost universal in continental Europe, and predominant in UK universities (UK schools insist on the ring form); however, both forms are defendable (and used in journals), and it would be impossible to police any style-preference.

I would also like to propose a secondary projet goal: to produce a style guide for chemicals articles, if only so that we don't have to go wading through Talkpages to remind ourselves what we decided! Current Wikipedia style advice is given at Wikipedia:Naming conventions (chemistry). Physchim62 22:23, 22 May 2005 (UTC)

I think the style guide for chemical articles is a great idea. I'd like to help. In addition, I believe a style guide for chemical reactions would also be helpful. ~K 22:31, 22 May 2005 (UTC)

NMR Spectroscopy

In User talk:Walkerma/Archive2, it was mentioned that the article Nuclear Magnetic Resonance concentrated on the physical phenomenon and left much to be desired on the analytical applications aspect of NMR Spectroscopy. It was also mentioned that a separate NMR Spectroscopy article should be written up covering these analytical applications using an NMR instrument. As of May 19, 2005, such a separate article has been written by User:Lee-Jon; see NMR Spectroscopy. Also, as of today, I have just written an article discussing the NMR standard tetramethylsilane, often called TMS. H Padleckas 08:51, 27 May 2005 (UTC)

Is it worth merging Haloalkane articles

Is it worth merging all those haloalkane articles? A number of them, although not very large, have enough unique material to be stand alone articles, instead of just stubs. I mentioned a counterproposal in Talk:Haloalkane, for what it's worth. H Padleckas 10:26, 30 May 2005 (UTC)

New activity proposed: structured indexing to all List of ...

Now that the list of compounds has been split in three structurally well-defined lists, I propose that we define another activity for our target provide navigational aids to chemicals in wikipedia, as defined in wikipedia:WikiProject Chemicals#Goals, viz., the structurally setting up of indexes to the lists, e.g., inorganic compounds by element (already going strong), organic compounds by carbon chainlength and biomolecules by molecular weight. Can we define a target shortlist, SMARTly? How do you all feel about this? Wim van Dorst 23:05, 2005 Jun 1 (UTC).

I encourage your efforts to bring organization to WikiChaos. However, your two suggestions are very problematic. Sorting compounds by chainlength works for simple organic molecules. Complex and cyclic molecules are much more difficult. How would you sort benzene, the three different isomers of xylene, or complex molecules like lovastatin? It just is not practical.

Let me make different suggestions. Most chemical companies organize their catalogue according to the Hill system order. (The elements in the formula are arranged by number of carbons, number of hydrogens, followed by all other elements in alphabetical order.) We could also organize organic compounds using the Hill order.

Regarding biomolecules, I think that we should mimick the WikiProject Drugs, and organize the biomolecules according to biological function. Molecules with several biological functions should be listed more than once. The list should also include proteins.

I hope this helps. ~K 02:48, 2 Jun 2005 (UTC)

An excellent suggestion. I must say I always envisaged a Hill formula order listing for organics as the equivalent of Inorganic compounds by element, I'm very glad others are independently thinking along the same lines. Incidentally, at RPI the chem stockroom used to be organised in Hill formula order- chemists loved it (much more natural than alphabetical for organics), but it had to be abandoned because of compatibility problems! As for the biomolecules, I think K's suggestion sounds like what I would choose, though I have to mention that I'm embarrassingly ignorant of biomolecules except for secondary metabolites.

However I think I'd like to suggest that we all take at least a fortnight's furlough from new administrative tasks to have a chance to write some good old fashioned articles! We now have a huge list of articles we have assessed as incomplete- we should also be trying to get to those. Even our beloved hydrochloric acid page still lacks supplementary material! The ongoing business of assessments and lists will still be there to be finished, I just don't want to add too much new stuff to the pile until loose ends from older tasks are complete. Walkerma 05:14, 2 Jun 2005 (UTC)

New activity proposed: chemistry style guide

Having said that, I don't think we should forget that we agreed with K's suggestions for writing a "Chemistry Style Guide." That was a great idea too, let's include it in our goals- but after a short break, perhaps? Walkerma 05:14, 2 Jun 2005 (UTC)

Walkerma, I think your idea is even better. Let's concentrate on some good articles now. If someone can start the "Chemistry Style Guide" page, then I'll start work on that. I have ideas about it, but don't know where it should go or what it should be titled. ~K 14:56, 2 Jun 2005 (UTC)

As pointed out by PC, a very reasonable start is available at wikipedia:Naming conventions (chemistry). That page can do with a new broom, indeed: it looks a bit like a talk-page. See at wikipedia:Policies and guidelines for recommendations how to do it. The title of Naming convention (chemistry) is reasonably apt, too. A self-defined new Chemistry Style Guide in wikipedia would perhaps be out of place. Besides, there are quite a few good Style Guides available for the chemical world: see for instance style guide for references. I recommend that we adopt a good official one, as we do follow IUPAC nomenclature, and abbreviate that for the wikipedia:Naming conventions (chemistry). Wim van Dorst 22:07, 2005 Jun 2 (UTC).

I think it's probably good to get this page looking more formal. Henry pointed out the Science Wikiproject standard on this, which should be borne in mind. Names are our biggest issue, but not the only one- I think a more general style guide is needed, because of issues of:

1. Coverage: There is a lot more to style than just names- conventions on structures & formulae, use of acronyms & abbreviations, references, units, language style, use of infoboxes, when & how to include experimental conditions, mechanisms, etc. Many of these issues are specific to chemistry, while others have certain aspects that are specific to chemistry or chemistry conventions.
2. Audience: Many people reading our articles are non-chemists, struggling with even basic concepts. Those familiar with my articles know that I don't avoid putting in technical info, but I also make sure there is plenty in the article that a high school kid could get from the article for their term paper. A JACS paper can assume that its audience understands a good deal of chemistry- we can assume that many do not. I learnt this on my second ever article when I was taken to task (quite rightly, in my opinion) for not explaining the "(I)" in the name.
3. Medium: An online encyclopedia is a lot different from a JACS paper. We are online, with an emphasis on wikilinks. We have issues not even discussed in the ACS style guide: Should journals such as Journal of the American Chemical Society be wikilinked from the reference? If yes, should it be once in the refs section, or in every citation? What about authors? Also, do we recommend that certain headings be present in the article- such as chemical properties, preparation, uses, etc.? (These were in the main template, but got lost somewhere in an edit- would people mind if I put these back in?)
4. Boundaries: This is a whole issue we need to discuss separately- how do we deal with our interface with physics, geology, pharmaceuticals/medicine, biology, etc? We can't impose our style on the paracetamol article- so what is appropriate?

I think that simply referring vaguely to published style guides is not the answer, namely:

1. Which style to follow, where IUPAC has nothing to say? RSC, ACS or whatever you feel like?
2. Most people composing articles will not have the ACS style guide (which would be my first choice as a starting point) on their desks- so we need to spell out the basics online.
3. As mentioned above, some of the issues are specific to Wikipedia.

As I mentioned above, I want to focus my energies in the next couple of weeks on adding content, but I am willing to participate in writing such a style guide if others think it's worthwhile. Walkerma 21:44, 3 Jun 2005 (UTC)

Strong agree. I will try to put a starter document together so that we can fill in the gaps. Physchim62 22:23, 3 Jun 2005 (UTC)

Strong agree. Well put Walkerma. You said it better than I ever could have. ~K 02:59, 4 Jun 2005 (UTC)

Strong agree. ‣ᓛᖁᑐ 09:44, 4 Jun 2005 (UTC)

Strong bullocks (just kidding, Martin). Of course I agree with your proposal. And I see a sneak preview on PC's pages, which is growing in an excellent way. Why not putting the text directly in the wikipedia:Naming conventions (chemistry) article, PC? Then we can have a discussion about the set up as well as the content. (PS. Your Title paragraph is spot on!). Wim van Dorst 11:57, 2005 Jun 5 (UTC).

• Aaargh! I've been caught being BOLD! The page Wim is referring to is User:Physchim62/Style_guidelines. I'm playing around in my userspace exactly because I'm not sure what will be the best place for each section. I will copy the Title section to Wikipedia:Naming conventions (chemistry) this evening if

1. It is complete enough to go into the Wikipedia namespace;
2. I am not proposing anything too far from current accepted practice (I don't think I am, but I want to go a have a beer and come back and reread it to make sure :)

Other moves will depend on how far I get with it! Physchim62 12:13, 5 Jun 2005 (UTC)

Proposal for new stub templates

Proposal copied from Wikipedia:WikiProject Stub sorting/Criteria

{{inorganic-cpd-stub}} and {{organic-cpd-stub}}

The cpd stands for compound. These two stubs would help take some of the pressure off {{chem-stub}} (currently over 1000 stubs). At a rough estimate, I would say 200 articles for the former and 300 for the latter. The image from {{chem-stub}} could be retained. Physchim62 01:31, 8 Jun 2005 (UTC)

{{Inorganic-compound-stub}} and {{organic-compound-stub}} are now up and running: 160 articles in the former and 360 in the latter... Physchim62 20:29, 17 Jun 2005 (UTC)

• Good work, PC. I saw them already come along on a few pages on my watchlist. But how on earth do you succeed to edit up to five (5!) pages in one (1!) minute? Apart from the editing work itself, I have to wait more than 1 minute per page for loading/opening for edit/saving. Wim van Dorst 20:38, 2005 Jun 17 (UTC).
  • I am on an academic connection, so download times are relatively rapid and I can cope with parallel downloads into different thumbnails. The editing was often just copy/paste work, although I did manage to do a bit of cleanup at the same time. All the same, it took nine hours of editing to work through the list (or an average of a minute a page)! Physchim62 21:48, 17 Jun 2005 (UTC)

We appreciate it, at least! Walkerma 21:57, 17 Jun 2005 (UTC)

A-Class articles

Our current criteria for A-Class articles are:

The article provides a well-written and complete description of the chemical compound, as described in Wikipedia:How to write a Great Article. It includes the full standard infobox table of chemical and physical data, and an appropriate series of headings to break up the article. It should have sufficient external literature references, preferably from the "hard" scientific literature rather than websites. It should either have a properly drawn (ChemDraw or equivalent) structure for covalent compounds, or preferably a photograph if it is a simple ionic compound. It should be at the stage where it could at least be considered for featured article status.

Four articles currently reach this standard: Iron(III) chloride, Phosphorus tribromide, Toluene and Zinc chloride.

In order to reconcile our assessment guidelines with the assessment practices of the different project participants (it wasn't just me who did the assessments), I propose the following criteria:

The article provides a well-written and complete description of the chemical compound (or group of compounds). It follows the relevant style guidelines, including those of this project, and needs at most minor editing before it could be considered for featured article status. Any remaining points to be resolved should be mentioned on the worklist.

Comments? Physchim62 22:20, 5 Jun 2005 (UTC)

I think this is reasonable. I originally proposed a more complicated system with more levels, and we might have assessed more as "B" under that system. But I think that system was too onerous on the assessor, particularly when most of our articles are a long way from even B-class. I'd be happy to go along with the revised guideline for A-class, with one addition- could we require at least one external reference? This might just be March, or Greenwood & Earnshaw, or the Merck Index- or even just the CRC Handbook- just something that shows we didn't just download some data from some crazy website. Once we get to the stage where we have most of our goal list being A-class articles, then might be the time to "raise the bar" where appropriate. Walkerma 03:58, 6 Jun 2005 (UTC)

• I would say that the "one reference rule" is covered by Wikipedia:Cite your sources, although I would permit a reliable web source, such as Sigma-Aldrich Co. to qualify. Personally, I use the Aldrich catalogue for data far more often than the Rubber Bible!

Physchim62 04:58, 6 Jun 2005 (UTC)

Albeit that I profess to be very much in favour of practicality, I d on't think we should downgrade our duly balanced A-Class before we have even started. Therefore I remain strongly supporting Martin's original 'tough' definition, boiling down to very realistic and imho important requirements:

• well written and complete
• appropriately sectioned
• full chembox infobox (or better)
• well drawn picture or photograph
• sufficient external references (1 can be enough)

As all of these are of course still subjective requirements, I also strongly support PC's proposal for a peer-review page for A-Class articles. Wim van Dorst 08:47, 2005 Jun 6 (UTC).

Phosphoric acids and Phosphates

I am in the process of writing a new article called which I plan to call Phosphoric acids and Phosphates. It is currently on the following Temp page: User:H Padleckas/Temp (Phosphoric acids and Phosphates), because I have not created the main illustration yet. A section at the bottom of this temp article: User:H Padleckas/Temp (Phosphoric acids and Phosphates)#Phosphate and Phosphite Esters covers "Phosphate and Phosphite Esters" until a separate article on the subject can be developed. Two images of general chemical structures have been included in this section, one of a phosphate triester and one of a phosphite triester.

If anybody has any philosophical comments on this endeavor, let me know. H Padleckas 16:32, 19 Jun 2005 (UTC)

• I don't see any problems, unless this article is supposed to supplant a proper treatment of the most important at Phosphoric acid. Otherwise, it is a useful collection of information on compounds which we're not going to get round to anytime soon. Physchim62 16:45, 19 Jun 2005 (UTC)

No, this is not a substitute for a chemistry section of orthophosphoric acid, currently and reasonably called simply Phosphoric acid. Eventually, I think the (ortho)phosphoric acid article should have its own "Table of Properties", a mention that it's a triprotic acid and mention of the three different K_a (and pK_a values), mention of the commonly used syrupy 85% aqueous o-phosphoric acid reagent, a link to the (ortho)phosphate article, a link to the future Phosphoric acids and Phosphates article, the use of o-phosphoric acid in buffer solutions, rudimentary safety discussion, links to MSDS, and any other chemistry aspects exclusively of only orthophosphoric acid. Similar discussions also apply to the (ortho)phosphate article, where its basicity, etc. is covered. However the rather stubby Trisodium phosphate article may be merged with (ortho)phosphate ?? Alternatively, Trisodium phosphate may be kept as a separate chemical compound article with its own "Table of Properties" and photo of the solid. H Padleckas 17:49, 19 Jun 2005 (UTC)

• Trisodium phosphate and sodium phosphate have their own problems which are not going to go away with a generic phosphate article, but that doesn't mean that we don't need phosphate as well. Just think of the need to provide an overview of structural types (something we are weak on at the moment, possibly for technical reasons), important minerals, the industrially and commercially most important phosphates, the biochemical importance of phosphates... OK, let's stop dreaming and start writing ;-) Physchim62 19:04, 19 Jun 2005 (UTC)

Fixed broken tables bug

Someone on IRC reported the tables at Wikipedia:WikiProject Chemicals/Organization being broken since the upgrade. I found that the problem was caused by having multiple "colspan" attributes on the table cells -- there's one in template:chembox header and another one explicitly set. On the older version of the software, the 'HTML tidy' postprocessing removed the first one (from the template) and kept the second one, while the new HTML fixup code in MediaWiki 1.5 kept the first one instead, causing the table to be formatted rather differently.

I've changed MediaWiki's fixup code to behave the same way as tidy, keeping the last instead of the first when there are more than one, and the tables appear to be rendering as intended again. --Brion June 29, 2005 21:56 (UTC)

Very good work. I have been looking into the problem as well, but I didn't know how to do it. Thanks for helping out. Wim van Dorst June 30, 2005 19:43 (UTC).

Peer review of guidelines

The starter document is now at Wikipedia:WikiProject Chemicals/Style guidelines, and open for comment and improvement. Peer review is particularly requested for the Title section, in view of replacing the current Wikipedia:Naming conventions (chemistry). Physchim62 20:08, 5 Jun 2005 (UTC)

I missed seeing this document until today- what an excellent piece of work, PC! It's so refreshing to see balance and common sense after tearing one's hair out trying to combine a new page on ethyl ethanoate with a separate existing page on ethyl acetate (about 1 day after I posted a comment here about "Don't forget to redirect from alternative names!"). PC seems to have managed to pull together all of the random style features, IUPAC rules etc into one document- well done! I would like to propose that we adopt this style guide as soon as the initial peer review is complete. We should perhaps add a few more examples and a bit more "flesh on the bones" in places.

Title: One awkward grey area (not addressed) is what to do if there is a common name in widespread use that is non-IUPAC, and a slightly less common IUPAC name that is still widely used. I'm thinking of something like ferric oxide vs. iron(III) oxide. The former is more common, but the latter is the standard name in Aldrich, Alfa etc catalogues. I take the view that if a IUPAC name is in widespread use, and is the commonest name in chemistry publications, then this should be the preferred title, even if it is a little less common in the wider world. This is based on the assumption that chemical names used in (say) ceramics, mineralogy, astronomy, alternative medicine, etc simply represent the standard chemical names from 25-100 years ago, so over time the newer name will become more established in these fields also. I also followed the lead of User:Darrien, who has tried to eliminate all use on Wikipedia of the "IUPAC-not-recommended" names such as cuprous, ferric, etc.

As for the Stock name (e.g., Titanium(IV) oxide) vs. the "covalent" or "proportions" name (e.g, Titanium dioxide), I tend to use the names given in the common catalogues as a guide, and they tend to like the Stock system for inorganics. With TiO2 which has a well established name as titanium dioxide I have left this as is- but when I wrote the V2O5 page I put it as vanadium(V) oxide. I tend to use the Stock notation with metal compounds, even if the compound is covalent (as with gold(III) chloride for example), but I use the "proportions" name for nonmetal compounds such as phosphorus trichloride despite Alfa using the Stock name in their catalogue. This is based loosely on the guidelines from the [original IUPAC rules]. When I get to metalloids, I confess I was a bit torn, but having looked at the IUPAC rules I think I prefer the proportional name for these too- but should it be arsenic trioxide (as on the bottle label), or diarsenic trioxide, or arsenic(III) oxide? The draft guide recommends use of Stock names when ionic and "proportions" names when covalent, but I think this will be hard to pin down. For example- which Mo halides are covalent, and which are ionic? MoF6 is clearly covalent, but where on the line MoCl6, MoCl5, MoCl4, MoCl3, MoCl2 are you going to divide between ionic and covalent? Therefore I prefer to recommend Stock for all metal compounds (unless other names are much commoner), and "proportions" names for nonmetal and metalloid compounds- this is clear and unambiguous, even for contributors with only a basic knowledge of chemistry.

Thanks again, PC for superb work. Walkerma 21:28, 16 Jun 2005 (UTC)

I keep meaning to add a paragraph into the title section to deal with IUPAC non-recommended names which we insist on using in Wikipedia. A few examples (please feel free to find more):

• Ethylene oxide, not oxirane
• Phosphine, not phosphane
• 1-Methylpropyl, not sec-butyl (for technical reasons)

My reading of the Red book (the 2004 draft doesn't change much in this area) is that stoichiometric nomenclature is always recommended, but that Stock nomenclature is tolerated for ionic compounds with integral oxidation states. Obviously, WikiPractice is that we use Stock nomenclature for most transition metal compounds, except when there is a better alternative (See the general rule).

I vote disagree to allowing Aldrich to determine our naming policy, if only because of #UnspecifiedDeity knows how many minutes of my time I have wasted explaining to PhD students the (non)logic of their system, as in "Don't worry, after six months you'll remember that methanol is listed under methanol but ethanol is listed under ethyl alcohol". The best internationally-accepted name can only be determined by reference to a number of sources, if then. Physchim62 19:30, 19 Jun 2005 (UTC)

Ethylene oxide is a commodity chemical with its own acronym (EO) so I can understand the persistance of that based on the general rule. I have never heard a conversation where a chemist said, "So I added the tetrakis{triphenylphosphane)palladium(0)", but I grant you that you will see phosphanes often in papers- a good example of common usage vs preferred IUPAC. As for 1-methylpropyl etc, I hate that style, but it's the CAS naming system found in things like CA and Dictionary of Organic Compounds. Re catalogues, I agree Aldrich can't be our guide- but in fact Aldrich, Lancaster, Alfa and Strem all seem to use the Stock system to the nth degree. I think that these catalogues reflect the customer's own tastes, ease of alphabetisation, etc., and in turn they have an impact on usage by chemists. Things like methanol vs ethyl alcohol reflect their own version of the general rule. Living in the US has helped me realise some strange differences too- in the US people talk about ammonium hydroxide, whereas in England it's nearly always aqueous ammonia (strictly more correct). This general rule is hard to interpret at times. Walkerma 02:45, 20 Jun 2005 (UTC)

Pictures of chemical compounds

Just mentioning that I have posted some new pictures on Commons- best to start here. The compounds are Al & Ca sulfates, SbF3, Sb2O3, As2O3, Bi2O3, Na3PO4, KNO3, KMnO4, CaF2, Ca(OH)2, Na2S2O3, silicic acid, boric acid, CAN, PdCl2, CsCl, ZnO. I also redid pictures of KCl & LiCl (I'm getting better at taking then now), and uploaded a few older ones to Commons too. I will probably be adding a few more new ones this coming week too. I will add pictures to the pages where we have them as time allows this week, but if you are planning on working on any of the above you should take note. Also, if you have any requests for pictures, please let me know- this week is about the best week for it for the light- though be aware that it is extremely humid here, and my attempt at a new FeCl3 picture saw the sample turning liquid before my eyes! Walkerma 18:22, 12 Jun 2005 (UTC)

• Not the moment to ask for a picture of solid butyllithium, then ;-) Seriously, do what you can Martin, I will try to get them linked through to pages (even if I have to write a stub so that we have an article to put the picture on). Hydrofluoric acid (e.g., picture of a plastic bottle) and carbon monoxide (e.g., picture of a nice red cylinder) are A-Classers without pictures for the moment. Otherwise, any photos you can get of precious metal compounds would be very welcome (but beware, the chlorides are quite hygroscopic). Physchim62 20:22, 12 Jun 2005 (UTC)

I will try to get those you mention- we have both HF and CO out in use at the moment. No RhCl3 or IrCl3 or related Ph3P complexes, I'm afraid. We have tiny amounts of Rh2(OAc)4, Rh2O3, and Pd(OAc)2, and PtCl4 solution, I will snap these when I can, when the weather abates. Walkerma 23:29, 12 Jun 2005 (UTC)

• Careful with palladium acetate, as it is hygroscopic and a skin irritant/sensitizer ("not a lot of people know that"). Potassium cyanide and/or sodium cyanide are also articles missing pictures, if it's not too much hassle to get the key to the poisons cabinet! Cheers, Physchim62 07:36, 13 Jun 2005 (UTC)

Actually poisons are a problem, at least till August- I got a picture of As2O3 while I had the chance. Cyanides can't be handled without a special protocol, and guess who should be writing the protocol instead of writing Wikipedia articles! I want to use NaCN in my research next year, so I will be doing that. Walkerma 15:32, 13 Jun 2005 (UTC)

• Then I guess I'd better get on with the cyanide cleanup that has been at the top of my to-do list for ten days now... Not easy when U.S., British and French protocols disagree! Physchim62 06:29, 14 Jun 2005 (UTC)

I request a photograph of potassium dichromate (K₂Cr₂O₇), potassium (or Na if K not available) chromate (K₂CrO₄), and chromium trioxide (CrO₃). A photo of chromium(III) chloride and Jones reagent would be nice, too. Also, aqueous Cr(VI) solutions being reduced to Cr(III) and a purple potassium permanganate solution would be nice, but don't go through much trouble to produce it. Thank you. In return, I can make some structure diagrams for you if you like.  :-) H Padleckas 07:08, 19 Jun 2005 (UTC)

I will try to do this when I get the chance- probably some in early July. I tried taking a picture of CrO3 recently but couldn't get the top off the bottle! Such poisons are now locked away for a while, but I'll do my best! We have all 4 combos of salts (Na/K, chromate/dichromate). There is a picture of CrCl3 hydrate already at chromium(III) chloride- were you wanting a better picture? Walkerma 07:45, 19 Jun 2005 (UTC)

Thanks for your response. The chromium(III) chloride picture will make do, although the interesting "bluish-green" color doesn't show that well; it seems almost too dark to make out the color well. I wanted to show a picture comparing Cr(VI) color with Cr(III) color.
H Padleckas 07:54, 19 Jun 2005 (UTC)

Pictures of all and any chromium(III) compounds would be welcome. Physchim62 15:28, 21 Jun 2005 (UTC)

New A-Class peer review page

Following PCs proposal, I have created the wikipedia:WikiProject Chemicals/List of A-Class articles, and filled it with the current thirty, including the open remarks. Wim van Dorst 23:42, 2005 Jun 16 (UTC).

• Thanks Wim! That had been buried on my to-do list, but I will try and add some comments later on today. Physchim62 06:36, 17 Jun 2005 (UTC)

Seconded! This page is really helpful at focussing our attention on what needs to be done- and also the status table at the top of this page will be good at keeping track of the project as a whole. Thanks a lot, Walkerma 20:20, 17 Jun 2005 (UTC)

I have been working on the A-Class articles, and upgraded several with new chemboxes and additional data for them (can't get the speed of PC, I'm sorry to say ;-). Now I have completely revisited the list of A-Class articles, and found (in my humble opinion) seven full blown A-Class articles and some twenty with smaller and bigger issues to solve. I would appreciate others to add to the new remarks and/or solve the issues. Of course I keep working on them too. Would it be fitting to put a date on the upgrading to real A-Class work ('if not done by ..., these articles will be B-Classified')? Wim van Dorst July 5, 2005 21:05 (UTC).

I think this problem is not surprising, as we are in a transition period- the standard table only became standard a few weeks ago, so we're not doing badly. Can I propose that "Protein" be deleted from this project, as it is a general term like "aldehyde" or "carbohydrate". Can I suggest that we downgrade any remaining ones after August 31st, that gives us a chance to fix the "A-minus" articles and also to have holidays/vacations. Walkerma 6 July 2005 21:27 (UTC)

OK for August 31st as a deadline. Can we convert the table of A-minus articles into a list of headers, to allow a bit more discussion of individual cases? My objection to Folic acid is that there are so many references that I wonder about its NPOV status. The references should be changed to Wikipedia:Footnote3 format to facilitate future editing (this is classic example of where FN3 format is useful, to avoid referencing errors in future updates). Physchim62 8 July 2005 10:02 (UTC)

• Table is converted (I was already partly in the process). Please feel free to move your remarks about deletion or otherwise from this section to the pertaining section. Wim van Dorst July 8, 2005 15:27 (UTC).
  • I already included the above striked out, and the vote for deletion to that page. Wim van Dorst July 8, 2005 18:51 (UTC).

Amino acids

I added tables to all the amino acid pages. I put a strike through all the NO TABLE notices on the chemicals table. I'm not sure if this is proper practice, i'm sorry if its not. The tables do need proper IUPAC names put into them though. Does any one who is good at nomenclature want to do this? I have done a few but there are some that I don't know how to name. Thanks. Borb 14:23, 26 Jun 2005 (UTC)

Hi Borb, all progress is good progress. Editing the worklist to indicate that progress is also good. Please go on. Recommendations for continued work include using the full chembox instead of the short ones, and notably filling in the details. And it is acknowledged that the most work is in that last part of it. Thanks for participating in the Chemicals WikiProject. Wim van Dorst 20:24, 2005 Jun 26 (UTC).

No problems, Borb. Personally I prefer the short form tables on these articles for the moment, until we get round to writing the content that they need: just look at the corresponding German articles, which have long form tables with no more text content than we have... If no-one else gets round to filling them out before the end of the month, I will work on them when I get to the UK (otherwise, I can always do the French versions!). Don't forget to delete text content which is simply repeating content in the tables (ie, if there is no additional comment), and to delete table line which are inappropriate (eg, boiling points when the compound decomposes before melting). ¡Hasta Luego! Physchim62 4 July 2005 07:49 (UTC)

NFPA Diamonds

Hi guys, I designed an NFPA diamond (fire diamond) that can be used on the chemical pages. It's actually made up of three images, to make it a little easier for me, anyway. Here's how to use it:

• Replace the N with number that goes in triangle.
  • Health (blue) diamond: [[Image:nfpa_hN.png]]
  • Fire (red) and Information (white) diamonds:
    • Normal: [[Image:nfpa_fN.png]]
    • Reacts violently with water: [[Image:nfpa_fN_w.png]]
    • Oxidizer: [[Image:nfpa_fN_ox.png]]
  • Reactivity (yellow) diamond: [[Image:nfpa_rN.png]]

So, [[Image:nfpa_h4.png]][[Image:nfpa_f4_w.png]][[Image:nfpa_r4.png]] gives you:

Should we add it to the standard data table for the chemicals? Do you see any changes I should make? They really should be templates to be a little easier to put on the pages...does anyone want to create 100+ templates? ;-) Also, Walkerma said they should be a little smaller...I'll try to work on that a little later today. I put some of these on a few pages already...check sodium chloride, acetone, potassium chlorate, hydrochloric acid, and hydrofluoric acid. Let me know what you guys think. Addaone June 29, 2005 14:31 (UTC)

I think this is fantastic. Great work! I agree with Walkerma, in that they should be smaller. ~K 29 June 2005 16:29 (UTC)

I cut the images down to half-size. Addaone June 29, 2005 18:19 (UTC)

• It is a good idea to add a splash of colour to those dull infoboxes. And useful info too ;-). As they are now 25px wide, this is ok. Minor point: Would it be possible to make the non-diamond pieces of the picture really transparent? These corners oughtn't to have a colour, do they? Wim van Dorst June 29, 2005 20:44 (UTC).
  • Hey, that is interesting: on the acetone page, I made the diamond of 20px resized images, before the images themselves were reduced (I like 20px better than 25 px, btw). And there the background is already transparant. But on the hydrochloric acid wikipage, they background is grayish. Is this some MSIE oddity again? Wim van Dorst June 29, 2005 21:12 (UTC).
    • I forgot to mention that I removed the white background in the images...you're not going crazy, Wim van Dorst. =) Addaone June 30, 2005 02:17 (UTC)
• I don't think doing it is too complicated, although we ought to write it up somewhere, e.g., on the talk page of the infobox? Wim van Dorst June 29, 2005 20:48 (UTC). I already put it on wikipedia:Chemical infobox project page itself. Wim van Dorst June 29, 2005 21:12 (UTC).

So are we going to add the NFPA diamonds to the infobox template, or just add them afterwards when we have the information? ~K 30 June 2005 15:10 (UTC)

• I vote for include. Wim van Dorst June 30, 2005 19:40 (UTC).
• Add to template...I would add an "NFPA 704" row with a link to here. Addaone July 1, 2005 01:36 (UTC)
• Include the new smaller diamond. Walkerma 1 July 2005 05:37 (UTC)

There isn't much doubt, is there? So I put it in the formal chembox table. Note that I did not link it to the programming explanation but to the information about what the numbers mean. Wim van Dorst July 1, 2005 20:28 (UTC).

For reference the full range: (there is a hint here until Addaone gets to it). Wim van Dorst July 1, 2005 20:28 (UTC).

For everyones information, I've found a website that lists about a billion NFPA ratings on various chemicals. I put it on the NFPA_704 page, but I wanted to mention it here so it can get used. ~K 7 July 2005 04:07 (UTC)

Recommendation for deletion from the worklist

text moved to pertaining section on wikipedia:WikiProject Chemicals/List of A-Class articles#Protein

Dictionary of chemical formulas

This is an extensive though mostly unlinked listing that appeared out of the blue. I contacted the author already. It covers inorganics and organics, with a heavy emphasis on what I presume are semiconductor materials. The listing seems rather odd in what is put in and what is left out; the most important gold compound, gold(III) chloride is absent, yet obscure things like triethylphosphine gold(I) chloride are included. This may reflect the interests of the author, perhaps. Also some hydrates are listed as separate from the anhydrous compounds, although I cannot foresee the day when we have a separate page both aluminium bromide and aluminium bromide hexahydrate. Nevertheless someone has done a lot of work and the listing may be useful to the project. Walkerma 7 July 2005 16:58 (UTC)

Hello everyone! Here is the dictionary's mission statement: "That if one who is chemically naïve should encounter an unnamed instance of a formula of a chemical compound in a piece of literature (e.g. a textbook, esp. basic/elementary/introductory), then that such a one may look up such formula in this list and thereby find its name."

The formulae in the list have been ordered according to these rules:

1. Element A comes before element B, and B before C, &c.
2. Element A comes before element A_i where _i is a natural number.
3. Element A₂ comes after element A₁, and A₃ after A₂, &c.
4. Element Ax comes after element A.
5. Element Ay comes after element Ax.
6. Element Ay_j comes after element Ax_i no matter what the natural numbers i and j happen to be.
7. A comes before AB.
8. AB comes before AC, and AC before AD, &c.
9. A comes before A⁻; A⁻ comes before AB.
10. If element X comes before element Y, then compound AX comes before compound AY.
11. Parentheses should be ignored unless two compounds with parentheses are the same except for the subscript of the parentheses: ABC comes before A(BC)₂, and A(BC)₂ comes before A(BC)₃, &c.
12. The compound must have at least two atoms, otherwise it is an element or an ion, but not a compound. (The "dictionary" being a list of compounds.)
13. Hyphens (for single bonds) are ignored unless there is a tie. Likewise for equals signs (for double bonds) and equivalence signs (for triple bonds).
14. Question: should hyphens, equals signs, and equivalence signs be included, or should they be removed from a formula before the formula is included in the list?
15. Structural formulae can only be included if they are linear (one-dimensional) alphanumeric strings all of whose atoms are explicitly labeled, e.g.: hexane may be included as C₆H₁₄, CH₃CH₂CH₂CH₂CH₂CH₃, CH₃-CH₂-CH₂-CH₂-CH₂-CH₃, or CH₃(CH₂)₄CH₃ but not as ASCII art in which six C atoms and 14 H atoms are arranged like six black pieces and 14 white pieces on a go board. Structural formulae which are two-dimensional or three-dimensional cannot be included, e.g.: structure of rhombic sulfur, aniline, tetraphosphorus decaoxide, α-D-glucose, β-lactose, ATP, cyclopentanoperhydrophenanthrene skeleton, protoporphyrin IX, myoglobin diagram. No Haworth projections, no Fischer projections, no quasi-linear diagrams which look like sentence diagrams. A formula is includeable iff it is a string whose characters are any of the following: (1) letters, in upper or lower case, or in italics; (2) numbers, subscripted, superscripted, or otherwise; (3) plus and minus signs, esp. superscripted; (4) parentheses; (5) brackets; (6) hyphens, equals signs, and equivalence signs; (7) asterisks (or interpuncts), spaces, and periods. (Note: minus signs might be used instead of hyphens for single bonds, since minus signs are slightly longer.)
16. Dotted compounds (for complex ions) are first placed by ignoring the dot (interpunct or asterisk) and whatever comes after it, but if there is a tie with a neighboring compound then the compound after the dot will be considered. In particular, A * B comes after A. If C comes after B then A * C comes after A * B.
17. If A comes before B then A * C comes before B.
18. Question: should complex ions (esp. hydrates) be included at all?
19. Question: would interpuncts be preferable to asterisks for denoting complex ligations?
20. The same compound may be included more than once if it has more than one includeable formula.
21. Different names for the same formula may be included in which case they are separated by commas.
22. A formula may refer to different structural isomers in which case the names of the different isomers should be separated with the symbol ∨ (logical OR). If many isomers are known to exist but only a few of their names are included, then the last one included should be followed by ∨ &c. If several isomers have a collective name then if individual names are also included then the collective name should come first, followed by colon and the list of individual names.
23. Brackets (for coordination complexes) should be treated similarly to parentheses: ignore unless there is a tie.

Anyone who wants to is invited to edit the dictionary, adding new compound formulas, removing formulas, adding alternative names for a given formula, adding hyperlinks from the name of a compound to its article, &c. just as long as the rules (or at least the most important ones, such as the first ten) are followed. Anyway, in the future, if I get around to it, I might browse Wikipedia articles about individual chemical compounds and categories of families of compounds to see about adding more entries to the list, with their names hyperlinked to their articles, so as to increase the list's usefulness. —AugPi 23:30, 13 July 2005 (UTC)

Thank you so much for giving us such a clear explanation of the purpose and the layout- it makes a lot of sense now. We are planning a list based on the Hill system, but that (I thought) was going to be more aimed at the chemically literate person, to help locate Wikipedia pages on a particular compound if the user couldn't find it by name. By and large your organisation seems logical and appropriate for your goal. My comments (mainly replying to your questions) would be as follows:

• Regarding whether or not to include -, = etc in formulae, you need to consider what your naive student of chemistry is likely to find in their book. If the book uses both forms, then ideally you should have both. However, there are many cases (even simple ones like benzene) where you simply can't write the formula with text any other way than the molecular formula, C₆H₆. So I would suggest that you have a policy of initially just trying to write formulae without hyphens etc, then just add a few of the simpler formulae like butane later if you feel the need (this is what I think you did anyway!).
• I suspect that it's not necessary to include hydrates, as this would just add a lot of extra work for little gain. If they are included, the normal Wikipedia format uses · for hydrates. For complexes, that format is rather obsolete (at least 50 years old?), the usual way these days uses square brackets, as you have used. If by complex you mean things like Lewis acid/base adducts (e.g. BF₃·OEt₂) then I think the middot is the way to go.
• That makes me realise- what about all of those organic shorthands we use like Me, Et, Ph? And what about acronyms like DMSO? Or attached group acronyms like TBS or TBDMS? Do these lie outside the scope of the dictionary?
• Four more general points I would be thinking about: (1) Why is this user wanting to know the name? If it's just to answer their high school homework, I think they should think it out for themselves, not try to crib the answer from here without thinking. So why would this person be wanting to find out the name? What is the source of their formula- a textbook, a website, where? To work well the dictionary needs to satisfy that purpose. (2) How should the page be linked within Wikipedia? We can't link it from every formula- a link like NaCl should lead to the compound itself, IMHO. For the page to become well-used, we need to find a good way to integrate it with the current infrastructure. In time Google etc will pick it up, and once that happens, a user typing in the formula into Google may find your page, and that may become the main way in for many people. (3) We should try to link the listings to articles wherever possible, because the articles have the room to give all of the synonyms, full structural formulae, etc. It looks like this is happening anyway. (4) Take a look at Wikipedia:Naming_conventions_(chemistry), there are a lot of useful tips on naming, with links.

Thanks for all of your hard work, I hope this will become an indispensible part of the chemistry pages on Wikipedia. Walkerma 03:45, 14 July 2005 (UTC)

I for one am certainly not going to knock this. Most serious chemical reference works have a formula index, which is what this could easily become (as well as serving it's initial role of a dictionary, the two are initimately linked). I haven't had a chance to thoroughly study the indexing protocol yet, but as it seems based on the Hill system I have no major objections. Minor points for now:

• Editors should remember that many different compounds can have the same formula, especially in organic chemistry.
• En-dashes look better than hyphens for single bonds.

Middots should be used for hydrates, [square] brackets for complexes (except the simple P-block cases mentioned by Martin).

• The use of Me as an abbreviation of methyl is not to be encouraged (it causes problems for German speakers), other abbreviations should be listed at the appropriate place in the order of empirical formulae.
• Abbreviations which are IUPAC approved probably deserve their own list somewhere—we could even separate it into a IUPAC-approved section and a non-approved-but-widely-used section.

Physchim62 11:15, 14 July 2005 (UTC)

UPDATE: I have copied the rules (without questions) onto the talk page, and added a sentence on the article page that links to this. However, I notice that the page is already 60 kB long, we're supposed to keep things below 30, but it's only going to get bigger. Should this be split into organics and inorganics? Walkerma 06:15, 24 July 2005 (UTC)

Methyl isobutyl ketone

Does someone want to write a quick stub to replace this ****? Physchim62 09:56, 19 July 2005 (UTC)

I will put together a short stub, and move most of the text to the talk page (which seems more appropriate for a discussing issues like this). My old employer in England used to use MIBK a lot as an extraction solvent so I'm familiar with it. Walkerma 21:25, 19 July 2005 (UTC)

Now completed, a short article with table. Walkerma 06:29, 24 July 2005 (UTC)

Aliphatic compound expansion...

I happened across this article, Aliphatic compound, and it seemed like it could use some expansion, although, not being a chemist, I don't know exactly what. It's not listed on your worklist, so I thought I'd mention it here in case you'd like to take it in hand. Thanks for all your good work on Wikipedia! JesseW 08:01, 27 July 2005 (UTC)

• Hmmm. The article is internally inconsistent, therefore factually incorrect... Physchim62 10:37, 27 July 2005 (UTC)

Summer work

I have archived all the older discussions on this page, as a nice summer clean-out. This leaves only the active things to work on during the rest of the summer, notably all the things on the List of A-Class articles and of course the worklist of the Chemicals WikiProject. I wish everybody (including myself ;-) success with it. Wim van Dorst 21:11, 30 July 2005 (UTC).

Sodium Hypochlorite

Sodium_hypochlorite -- I cannot figure if the article has been vandalized to a POV or just hasn't been expanded. Please help.

I believe the article had been vandalised in minor ways several times recently, though it seems to have had these problems fixed. I don't see any obvious POV problem, though, so I agree with the removal of the POV notice. I'm watching this page from now on, though! Walkerma 21:27, 21 August 2005 (UTC)

Data book

I have uploaded collections of gas densities, viscosities and solubility products which people might find useful in filling out chemboxes. Enjoy! Physchim62 00:26, 26 August 2005 (UTC)

• Well done! A good contribution. May I suggest that you also put the Data Book in the Reference section of wikipedia:WikiProject Chemicals wikipage? Wim van Dorst 20:39, 26 August 2005 (UTC).
  • I'm on poor access for a week or so (returning from holidays), can someone else see to this please? Physchim62 16:14, 27 August 2005 (UTC)
    • Done, PC. Glad to be of help. Wim van Dorst 17:47, 27 August 2005 (UTC).
• One comment- what are the copyright implications of uploading large amounts of data on one page like this? I have a list of dipole moments, but I kept it to myself for this reason. Walkerma 03:12, 28 August 2005 (UTC)
  • If they are results of your own calculations, as they are apparently on PC's list, that wouldn't be a problem, would it? You wouldn't be talking about copyrighted books, would you? ;-) Wim van Dorst 21:37, 28 August 2005 (UTC).
    • We're OK for copyright on the data book, see Feist Publications v. Rural Telephone Service. Physchim62 08:45, 4 September 2005 (UTC)

Update of List of A-Class articles

• Just did some assessment work on the Problematic Preliminary A-Classifieds. I'm open for comments. Wim van Dorst 21:59, 26 August 2005 (UTC).
• An important question crops up: when officially upgrading articles to Chem A-Class via a peer review on the List of A-Class Articles, would it be deemed necessary to retain that tit-bit of discussion there? And if so, how? Personally, I for one won't need that archived. How do t'others think of this? Wim van Dorst 17:40, 27 August 2005 (UTC).
• I would go for archiving with sub-pages: I can sort this out quite easily when I get a minute of stable connection! Physchim62 17:46, 27 August 2005 (UTC)
  • Archiving it is (and done). Wim van Dorst 21:37, 28 August 2005 (UTC).

Entries on the Worklist

And shall we delete RNA and Peptide from the worklist, just as we did Protein and DNA. Wim van Dorst 22:04, 3 September 2005 (UTC).

• Yes please, we have enough problems with our target articles without going looking for anymore! Physchim62 20:30, 4 September 2005 (UTC)
  • Removal done. Wim van Dorst 21:01, 5 September 2005 (UTC).

On April 14, Martin added squalene oxide to our worklist. Is this intentional, or did you mean squalene. Wim van Dorst 22:04, 3 September 2005 (UTC).

• Yes, I did mean squalene oxide- it's an important biochemical intermediate in the biosynthesis of ALL steroids. I think it can be isolated from sharks (this is all from memory, don't quote me!), so it is an isolable compound. It does an amazing cyclisation producing all of the rings stereospecifically in one step! Walkerma 16:49, 5 September 2005 (UTC)
  • It is squalene that is known as Shark Liver Oil, and the first step from this is indeed the oxidation (squalene monooxygenase) to squalene oxide. And then you're right, it reacts onward to lanosterol and further to cholesterol. The intermediate compound isn't a particularly easy chemical compound to work on in this context: There is hardly any data available for it. That it has a very nice reaction mechanism, is that enough to warrant a listing on the WikiProject Chemicals worklist? I recommend replacement by squalene (status Chem Stub too, by the way). Wim van Dorst 21:01, 5 September 2005 (UTC).
• Sorry about that- I had thought that the epoxide was the compound in shark oil! Yes, let's make squalene the compound if its oxide is harder to pin down- we do after all need MP, solubility etc on a well-known compound. Thanks for unearthing that, I've lost by book on this topic. Walkerma 21:38, 5 September 2005 (UTC)

Which malonate

In the worklist the building block malonic ester is mentioned. Which ester would that be? PC already suggests dimethyl malonate, although diethyl malonate (DEM) is an alternative. Or would perhaps malonic acid be a better alternative instead? (I'm going for the unclassifieds, if anyone had noticed). Wim van Dorst 22:35, 12 September 2005 (UTC).

I've changed this to diethyl malonate and added dimethyl malonate to the list as well. Malonic acid is said to be relatively unstable, with few uses, so is probably not notable enough for this section. [2] ‣ᓛᖁᑐ 23:50, 12 September 2005 (UTC)

Let's just keep the diethyl malonate on the list and remove the dimethyl ester if PC doesn't mind. I'm making malonic ester as redirect to this. For the malonic ester synthesis, either ester will work fine, and since we have the ethyl ester now let's go with that for now. Walkerma 19:02, 13 September 2005 (UTC)

Pruning the Inorganics section

While working on reducing the number of Unclassifieds (mostly red links like this one) in the worklist, I took the liberty of pruning about nine Unclassifieds from the Inorganics section on the worklist. All were there as a second choice to elements where there was already a classified (Stub/Start or better) alternative. The removed entries have actually only been moved to below the Inorganics table, and can be put back when inadvertently I have removed the important compound in favour of a minor compound. It was all about the obscurer elements, so I hope this was ok. Please feel free to correct if necessary, of course. Wim van Dorst 19:23, 15 September 2005 (UTC).

Thanks, this was very useful- our goal is only to have one compound per element, we don't really need two rhenium compounds at this point in the project.

What sacrilige! Rhenium chemistry is vitally important for... ermmm... modeling technetium chemistry! (and for gaining this editor his MSc, but obviously I would not allow such personal judgements to cloud my reasoning ;) Seriously, I have finished the job and created substubs for all but one of the remaing elements. The one that is left is, errr, technetium: I will come up with an article on NaTcO4 (widely used in medical imaging) when I can get to a university library to check my facts. Category:Chemical compounds by element now has subcategories for all the naturally occurring elements except He, Ne, Ar, Kr, Po, As, Fr, Ac, Pa, as well as categories for Tc and Pu (83 in total). Physchim62 12:20, 18 September 2005 (UTC)

• Excellent to hear that articles on a rhenium compound as well as on a technetium compound may be expected in the near future on MCs level quality. That can hardly be a long way off from FA status! ;-). But thanks very much, PC, for filling all those Unclassifieds. There are now just five left, and I do think we can Stub them before the end of the month (next counting round). That's progress! And next month we'll move all Stub to Start, right? Wim van Dorst 23:24, 18 September 2005 (UTC).

Ethenol as building block

I propose that we omit this from the building blocks list, just because it's not an isolable compound on Earth at room temperature. Thus I think you would be unable to get MP, BP, density etc, and it is not used on Earth as a building block in an organic synthesis (though acetaldehyde, the tautomer, is a building block). Walkerma 20:22, 15 September 2005 (UTC)

I see; interesting. I'll take it out, then. ‣ᓛᖁᑐ 20:40, 15 September 2005 (UTC)

Benzene is a Featured Article Candidate

Hmm.... Well, head on over and give your two bits, if you want. ~K 18:49, 16 September 2005 (UTC)

Next chemistry FA?

OK, we've all been putting it off, but if benzene is not going to be an FA just yet, should we work on one? If it is to be a compound I think it should definitely be an organic compound, to complement the inorganic FA in the spring. An alternative could be a reaction or process, or perhaps a concept, but the compounds have been generally more peer reviewed because of this project. It also needs to be something the general person will have heard of or would be interested in (though please can we avoid illicit drugs!?). Benzene would certainly be a possibility, with some work it could be good. Do other people have suggestions Walkerma 04:57, 24 September 2005 (UTC)

• Looking at the List of A-Class articles for candidates, benzene isn't even listed as it is currently merely B-Class. Most outstanding organic compound there would be acetic acid, a good article already in its own right, and appealing to the general public. But my personal choice for FA-upgrade effort would be sodium sulfate, which is even more a properly balanced good chemical compound article. Wim van Dorst 07:36, 24 September 2005 (UTC).
  • I'd go with acetic acid as well. It is a good article, about a compound that most people have heard of. The problem with reactions and concepts is that we have little idea of what is out there and what the problems are: with compound articles we are in a stronger position to argue a case. Physchim62 15:32, 24 September 2005 (UTC)
  • Yes, let's propose Acetic acid and see what everyone else thinks. (I think the phrase is: Run up the flag, and see if anyone salutes.) Nothing can go wrong: either it becomes a featured article or it gets improved. Either way we win. ~K 17:37, 24 September 2005 (UTC)
    • Done. See Wikipedia:Peer review/Acetic acid/archive1. Physchim62 18:35, 24 September 2005 (UTC)
    • Now really done (you missed out on step 3, PC!), see Wikipedia:Peer review. I'm already working on further improvements. Wim van Dorst 16:28, 25 September 2005 (UTC).

Sodium hydroxide needs work

I'm no good at chemistry, but I know that Sodium hydroxide needs you guys' attention. There's no picture, the hard chemical data is mediocre, and a few other things are bad, too, see the talk page. Thanks! HereToHelp 20:49, 28 September 2005 (UTC)

I will work on this during October. It is definitely a poor page for such an important compound. Walkerma 21:51, 3 October 2005 (UTC)

A safety section is in progress. Physchim62 09:19, 4 October 2005 (UTC)

New member

I am sorry if I am spoiling anything but I would like to be somewhat involved in this wikiproject. Is that possible, as chemistry is my favourite subject?Xeno Neon

• sure, no problem. Just put your name on the wikipedia:WikiProject_Chemicals members list for registration, then find a Chem Stub article on the worklist, and start adding useful information to that article. And if you're done, just tell everybody about it on this page, so that the article can be re-assessed, preferably to A-Class. Success. Wim van Dorst 20:38, 3 October 2005 (UTC).

Welcome Xeno Neon! This Wikiproject focuses on writing pages on chemical substances, as listed on the worklist Wim mentioned. This wikiproject is certainly the liveliest area for chemistry at the moment, and we are making a lot of progress, but we could definitely use some help. We are trying to get 380 feature-article quality (or close) articles! If you don't want to work on specific compounds, then instead you can work on reactions like ozonolysis, particular chemists, organic functional groups or general aspects (e.g. Lewis acid). These are very loosely coordinated through Wikipedia:WikiProject Chemistry. There are also separate projects on polymers, elements and isotopes. If you look on my user page I have a list of the most useful pages (lists etc.) for chemistry. This is a friendly group so please ask for help if you need it. Walkerma 21:31, 3 October 2005 (UTC)

A useful website

For information on chemicals, go to http://www.chemicalland21.com and click on one of the colored bars in the left frame
(Industrial chemicals, Life science products, etc). Note: I have no connection to this site. I just discovered it 30 minutes ago, and it's been helpful.

If anyone has any other useful resources, please add them. Twilight Realm 23:06, 12 October 2005 (UTC)

• This is a commercial website with copyrighted info. Nonetheless, very helpful for public data too, and I use it a lot too. Recommended. BTW. When I use this site (or any site) for a significant amount of data (typically chembox), I add the direct link to the References. Wim van Dorst 23:09, 13 October 2005 (UTC).

Suggestions

There should be a section at the bottom (or top) for people to add suggestions of chemicals to work on. Twilight Realm 03:28, 13 October 2005 (UTC)

• You couldn't have missed the worklist, could you? Wim van Dorst 23:10, 13 October 2005 (UTC).
  • There is also Wikipedia:WikiProject Chemistry/Requested articles. (needs to be better signposted, I know) Physchim62 06:27, 14 October 2005 (UTC)

I don't consider the worklist to be open, since you can't really add a 31st reagent when there are supposed to be only 30. I realise that people ignore that, but that's perhaps because we don't have a "suggestions box." As for requested articles, that is more appropriate for WP Chemistry, as it covers all chemistry articles- this seems like the right place to suggest an article on, for example:

• Silver(I) oxide

Next milestone: no unclassifieds

Hi all, with the last worklist compound ethyl bromoacetate now having an nice stub article (I even unhumbly classified it as Chem Start), we have now reached the stage that we can only go up. There are no unclassified to drop off any more (e.g., zirconium(IV) chloride), nor are there obvious articles to be weeded from the list as they might be vague as a single compound (e.g., Protein and DNA). So in a week or so when we make up the next statistics table, the total number (380 if I counted right) is consisting of only real articles! Wim van Dorst 22:32, 23 September 2005 (UTC).

Free beer!

Thanks for your work on getting stubs going and tables put in place, Wim and Eequor! You are both hereby offered a free beer in Potsdam, New York, next time you visit our great metropolis! Walkerma 04:44, 24 September 2005 (UTC)

I meant to thank you for this... though I don't know when I'd be able to take you up on the offer, and I don't drink anyway. ^_^ ‣ᓛᖁᑐ 04:18, 23 October 2005 (UTC)

Featured articles from German

I came across de:Alkane as a (deservedly) featured article in the German Wikipedia, and I'm in the process of translating it into English for here. Other German featured articles of interest to us are Ethylene, Benzene, Toluene and Anthocyanin, as well as Arsenic and Barium among the elements. Anyone else interested in a bit of translation work? Physchim62 12:47, 16 October 2005 (UTC)

Rephrasing proposal for Stub and Start assessment

While attacking the Chem Stubs in the list, I found those that should in my humble opinion be Chem Start and simultaneously I found Chem Starts that should be Chem Stub. The fine line between the two should be drawn a little clearer, therefore I propose the following rewording of the wikipedia:WikiProject Chemicals/Assessment

Grade	Description	Summary
Stub	The article is a very short article or a stub that will need a lot of work to bring it to A-Class level. It may lack most or all significant sections.	limited text, no chembox, no refs
Start	The article is short, but has some good sections, such as a chembox data table description of uses, production and/or chemical and physical properties. It may lack several signicant sections.	some text+chembox, limited in the sections

I could think of a rewording in this line for B-Class as well, but I'm not working on those yet. The rephrasing for Stub and Start would make it possible to re-categorize all Stubs and Starts into proper work targets (viz., no Stubs and at least Starts). Wim van Dorst 12:54, 23 October 2005 (UTC).

• Already I did the re-assesment of all Stubs, but (disappointingly to me at least), not as many (~25%) as I had expected (~75%) could seriously be upgraded. Just shows that there is still a lot of work. Wim van Dorst 14:16, 23 October 2005 (UTC).
  • I tend to grade solely on the text quality. If the text is long enough to have sections, it's a {{Chem Start}}; if not it's a stub. Chemboxes and refs come in (among other criteria) when I make the grading start/B-class. Physchim62 17:21, 23 October 2005 (UTC)
  • Yup, so did I now. Wim van Dorst 17:36, 23 October 2005 (UTC).

Sounds fine to me. I treat the chembox as "content"- so a lot of text + sections but no chembox is a start, and so is less text (a couple of sections) with a chembox. There have been a couple of starts that I thought should have been stubs, such as tellurium dioxide and ethyl bromoacetate, but instead of complaining I just added enough to make them starts. Also, section headings without content should not be seen as adding much content! Other than that, I think your clarification is excellent, thanks. Walkerma 16:48, 24 October 2005 (UTC)

Templates for R- and S-phrases

Now that I have a liitle bit of time to breathe, I am in the process of implementing a chemical safety project that Eequor and I discussed over the summer. Each code for the R- and S-phrases will correspond to a template (I've done most of the R-phrases so far, hope to finish this weekend): for example, R45 corresponds to Template:R45, and when you type {{R45}} you see {{R45}} on the page. Now hold the cursor over the link...

The templates use the {{abbr}} template: for the example above, the code is {{subst:abbr|May cause cancer|R45}}.

The official R- and S-phrases for any compound may be found on the site of the European Chemicals Bureau:

• Click "Classification & Labelling"
• Click "SEARCH CLASSLAB"
• Click "Search Annex 1"

Feel free to use these templates liberally, in the interests of public information! Physchim62 06:44, 22 October 2005 (UTC)

• All the templates are now up and running, see them in all their glory at List of R-phrases and List of S-phrases. Some of the S-phrases require information to be supplied by the manufacturer: we will have to address this at some point (e.g. by adding arguments to the templates) but for the time being I'll leave them as they are. Enjoy. Physchim62 22:01, 23 October 2005 (UTC)
  • Excellent. Best thing I've seen in a long time. Very smart. I'll use them where ever useful (just did hydrochloric acid. Wim van Dorst 22:45, 23 October 2005 (UTC).

Acetic acid to FAC?

Hi all, acetic acid has been up for a month on Peer Review (read archived text here), during which it saw numerous improvements even after it had been classified already as Chem A-Class. The current article is to me now excellent enough to be proposed for FAC. Shall we move on? Wim van Dorst 14:55, 24 October 2005 (UTC).

Let's go for it. ~K 15:12, 24 October 2005 (UTC)

I'd like to hold off for a few days. I think there is still some cleanup to do, and I'd also like to create a few stubs for things like isobutyl acetate to reduce the red links. Not too long, though! Walkerma 16:51, 24 October 2005 (UTC)

I agree with Martin, it can wait a week or so more to try and finish the polishing and reduce the number of red links. Physchim62 17:49, 24 October 2005 (UTC)

• What red links? (Ooo, that feels good to write, after cobbling up all those stub articles that one still wants to make something serious out of). Cacycle is doing some serious last minute cleaning up now, so after that? I'd say go for it! Wim van Dorst 22:51, 25 October 2005 (UTC).
  • I claim paternity for Showa Denko and Heteropoly acid! I agree in so far as I think we're not going to get much further without a bit more outside comment: let's send it to FAC and see what they throw back at us! Physchim62 (talk·RfA) 18:15, 1 November 2005 (UTC)

Let's see if there are any more improvements in the pipeline... (but I still think we're near the point where we should move on to the next step). Physchim62 (talk·RfA) 18:43, 1 November 2005 (UTC)

I would like to review Acetic acid this afternoon or this evening. H Padleckas 18:24, 1 November 2005 (UTC)

I've been extremely busy at work over recent weeks, but I got a breathing space to put in some stuff this afternoon on the applications section. (Sorry I created three new red links, but only got rid of one!) I still would like to insert a bit more on chemical properties (I think it's a bit weak there), but that's about all. I think it'll be ready to submit tomorrow, so we all have a chance to give it a final look over. Walkerma 21:14, 1 November 2005 (UTC)

I'm finished with my additions. Please feel free to delete or edit parts you don't think are appropriate. I'm conscious of the fact that when we did HCl we explained even what an acid was, whereas this time we wrote for a more advanced reader. I tried to put a little more basic info in for the schoolkid and the student, e.g. the equation for the baking soda/vinegar reaction. I also added a nice book ref which may be more accessible to a lay reader than obscure Japanese journals. When chemists peer review chemists, we can forget that non-chemists may be reading the final article! I vote for sending it for FAC later on Nov 2nd. Walkerma 23:34, 1 November 2005 (UTC)

There are a couple more rather minor changes I would like to make to Acetic acid. Then it could be submitted as FAC. Unfortunately, I was unable to make them last night because of a malfunction of some sort; my computer or internet service provider did not let me get access to Wikipedia pages.
H Padleckas 17:01, 2 November 2005 (UTC)

I will now write up some philosophical comments about the Acetic acid article in the talk page after my review and a few edits I made. H Padleckas 00:47, 3 November 2005 (UTC)

It is up on WP:FAC now!!! Wim van Dorst 23:11, 3 November 2005 (UTC).

Congratulations to all who worked on Acetic acid, which has now become a Featured Article in Wikipedia. H Padleckas 08:43, 13 November 2005 (UTC)

• Yes, thanks and congratulations to the whole WP:Chem team and many others. I think we can be proud of this joint achievement! I propose we do another in a couple of weeks (months?) time. Wim van Dorst 15:24, 13 November 2005 (UTC).
• Further support entries would be appreciated on wikipedia talk:Tomorrow's featured article. ;-). Wim van Dorst 16:19, 13 November 2005 (UTC).

Article assessment templates

I've added a couple of templates we might use to keep track of article progress. These are {{inorganic-compound-start}} and {{organic-compound-start}}: {{inorganic-compound-start}} {{organic-compound-start}} Each of these has a category for its articles, Category:Incomplete inorganic compound articles and Category:Incomplete organic compound articles. The idea is to list all the {{chem start}} articles, including those not on the worklist. How does this sound? ‣ᓛᖁᑐ 18:58, 25 October 2005 (UTC)

Hi, Eequor, aren't these just euphemisms for {{inorganic-compound-stub}} and {{organic-compound-stub}}? What the profit to use yet another set of templates? Wim van Dorst 20:45, 25 October 2005 (UTC).

I was thinking of using these on articles that were no longer stubs, but not B-class either. ‣ᓛᖁᑐ 21:05, 25 October 2005 (UTC)

Thanks- seems good to me! We probably need to make sure people outside WP:Chem know what they mean, though. Walkerma 05:22, 26 October 2005 (UTC)

Yep, lets see how they work, and if the categories actually get populated. Chemistry is an experimental science, after all! Physchim62 11:53, 26 October 2005 (UTC)

How to handle isomers (again?)

Although this has been discussed before, Henry proposed an interesting proposition about how to handle several isomers of one compound. Together with our own style guides, I would like to word it as follows:

• Compounds as dioxane, triazine and MDI may have a {{disambiguation}} page for the generic term. Unimportant isomers get redirected to the generic term.
• The real article is at the most important compound out of the series, e.g., 1,4-Dioxane, 1,3,5-Triazine and 4,4'-MDI (note the capitalization and the inclusion of numbers etc in the title)
• Other pages get redirected to the real article, viz., those with lowercase titles and with other names for the same isomer
• Alternative by Henry: the other isomers get treated as a paragraph in the real article, and the generic term gets redirected to the main article too, viz. dioxane redirects to 1,4-Dioxane and triazine redirects to 1,3,5-Triazine. Then the other isomers get redirected there too: 1,2-Dioxane redirects to 1,4-Dioxane too.
• We only include the articles for the most important compound in the worklist
• This leaves us with compounds with several important isomers, e.g., n-Butane (sic!) and Isobutane, the phthalic acids, and many others, which where discussed before: they simply get a real article each.

If we can agree to this, perhaps this should be part of the styleguide? Wim van Dorst 08:37, 29 October 2005 (UTC).

Thanks for making a clear proposal—I for one know how difficult it is to write clear guidelines! For Dioxane, I favour the following:

• • The main article should be at 1,4-Dioxane.
  • Dioxane should redirect to the above.
  • 1,4-Dioxane should have a disambig comment as the first line:

This article discusses 1,4-dioxane: for other isomers, see Dioxane (disambiguation).

In general, I am opposed to including several different compounds in the same WP:Chem article, as I feel that it makes life more difficult for the user. That's not to say that I think that generic articles don't have their place—quite the reverse—but they are most useful if they are immediately recognisable as generics. If I want information about isophthalic acid I don't want to search in the phthalic acid article, although I might accept having to search in an article about phthalic acids.

As this issue involves article titles, and hence a clarification at Wikipedia:Naming conventions (chemistry) and not just in our style guidelines, can I ask everyone to give their point of view. I will take this opportunity to raise another similar point below. Physchim62 21:23, 29 October 2005 (UTC)

I think we should recommend single compound articles initially unless (a) no single compound is of note and (b) it is unlikely that anyone would ever write an article on the separate isomers. If someone feels the need to write a "family page" like phosphorus halides that paints a broader picture, that's fine, and appropriate for things like dioxin, but it shouldn't replace separate articles for major compounds (like PCl₃). The third option, having a page focussing on the major isomer but mentioning others I think will be useful in certain cases. For example heptacosane will never have a separate article for all (many thousand) isomers, nor is it worth writing one page for n-heptacosane and another for all the isomers. In summary:

All isomers/compounds are notable to some extent: Single compound pages. No single isomer of note: One page for all. One single isomer of note, other isomers not notable: Single compound page and isomers page, unless this is not deemed worthwhile, in which case one combined page. Large no. of related compounds, some of which are related: Family page + single compound pages. Walkerma 14:13, 30 October 2005 (UTC)

Also see List of multi-compound articles below at the end of #Groups of chemical compounds: thiophenols, toluidines. H Padleckas 11:04, 15 November 2005 (UTC)

Acids and anions

For the moment, there is no guidance on creating articles about acids and their conjugate anions. The following proposal is current practice, I will add it to the guidelines if there is support among editors:

• Inorganic anions have individual articles which discuss the chemistry of their salts in addition to the article about the parent acid. The parent acid has an article even if it is only stable in solution (see also sulfurous acid).
• The names of all but the most common organic anions redirect to the article on the parent acid (Exception: acetate).

Again, comments please. Physchim62 21:23, 29 October 2005 (UTC)

Sounds good. Walkerma 02:13, 30 October 2005 (UTC)

Metal compounds

While we're talking about these sorts of issues, it seems to me that we have a big need for pages that cover the chemistry of a metal in its compounds. Non-metals get the equivalent- we have oxygen and oxide, chlorine and chloride, so why not iron and iron compounds (or compounds of iron or chemistry of iron)? The element page clearly focusses on the metal itself, with compounds as a simple add-on. The individual compound pages are too narrow a focus to cover the whole chemistry. And more obscure compounds that perhaps one interesting aspect either get a silly stub, a random mention on another (random) page such as the chloride (e.g., you can make this interesting complex from MCl₃), or you get nothing. It would give a broader view, reviewing all of the compounds e.g. from Fe(CO)₅ to FeSO₄ to haemoglobin, all in one article. I'd held off even mentioning this idea knowing that we already have a mountain of work to do- but as we plan the future direction of substance articles I thought it was worth mentioning. Comments anyone? Walkerma 02:25, 30 October 2005 (UTC)

Good idea. What do you have in mind for the layout and content of these articles? ‣ᓛᖁᑐ 03:33, 30 October 2005 (UTC)

I'm not convinced, especially not by the example you give. People write entire books on iron chemistry, a single article could never be comprehensive. However I accept the point you are making, we are going to have to do something about the problem. For the example of iron, we will need articles on Low oxidation state complexes of iron, Biochemistry of iron, possibly something like Aqueous solution chemistry of iron, not to mention Analytical chemistry of iron (enough material there for an article). We also, IMHO, need to take care about the coherence of our approach with the material that appears in the artcle about the element, which should contain a very short introduction to the chemistry. For some elements (Astatine springs to mind), everything can go on the element page but these are obviously the minority. I don't think we can have a "one size fits all", inorganic chemistry just doesn't work like that! Physchim62 09:19, 30 October 2005 (UTC)

• Isn't this askind for a HUGE amount of work? Why not first do good work on iron(II) sulfate (proposed only), iron(II) chloride (not listed), Iron(III) oxide (Start) Iron(II,III) oxide (not listed) to make them all A-Class, and then consider extra work? Wim van Dorst.

WikiProject Polymers

This last summer WikiProject Polymers was initiated in Wikipedia. During the last couple of months, more participants have signed up and this WikiProject is starting to become more active. For example, H Padleckas has signed up to participate.
On the WikiProject Chemicals/Organization page, there is a list of Polymers. I would like to suggest moving this list over to WikiProject Polymers. Being active Wikipedia participants, you can still work on these polymer articles over there too and sign up like I did. Does this seem OK to you guys? H Padleckas 06:35, 1 November 2005 (UTC)

• I second this idea: I've been meaning to propose it myself but I keep forgetting to! Physchim62 (talk·RfA) 09:45, 1 November 2005 (UTC)
• Just as long as a combined effort we get the total up to a high level, it is fine with me. If we want to retain the overview of the whole in the status tables, then we should keep it in one long table. But in the WP:Polymers is it already clearly signposted as the target, so I don't think it is a big deal either way. Wim van Dorst 21:38, 2 November 2005 (UTC).
• Great idea! Polymers have always been an awkward fit here, because many of the standard substance descriptors don't apply well, but when the goals were set it was considered important not to ignore/neglect this important field. WP:Polymers was just a twinkle in someone's eye back then, now it's taking off. They should take over this list, and hopefully they will adopt our system of oversight & assessment so we can compare notes etc. If the Polymers folks want to leave the table where it is, that's fine too - but they should take control of it either way. Walkerma 08:19, 4 November 2005 (UTC)

Inorganic starts

I'm currently working through the chemboxes on inorganics articles, creating data pages and listing MSDSs etc. It struck me that some articles which have been assessed as starts are really only stubs, so I went through the entire list of inorganic starts. The articles to which I refer are:

• Beryllium oxide
• Bismuth trioxide
• Cadmium sulfide
• Calcium carbonate Now stub
• Hydroiodic acid Now stub
• Lithium hydroxide
• Magnesium carbonate Now stub
• Mercury(I) chloride
• Tantalum(V) chloride Now stub
• Tellurium dioxide
• Tin(IV) chloride
• Ytterbium(III) oxide Now stub
• Yttrium barium copper oxide Now stub

Can someone else have a look over them and regrade if necessary. Physchim62 (talk·RfA) 12:38, 1 November 2005 (UTC)

We may be suffering from a little grade inflation! I partially agree with PC, and I suspect that some of our organic starts may be a little too brief also. I have regraded some of the above on our worklist, see the list above for changes. I think it's not too simple to make assessments, however. There are various complicating factors:

1. Table vs. no table. For a page like beryllium oxide, if we took out the table and turned the table information into prose, it would probably pass as "start" quite easily because it would look much longer – remember that the table is a very concise way of providing information. We should not penalise a page for being concise! Hence I have left some of the above as starts.
2. Scope of subject. For a page like calcium carbonate we know that there is a Mg of information out there, so we would expect the A-class article to be long, with a wide variety of sections. With tantalum(V) chloride, much less is known, and we would expect it to be narrower and shorter. (Likewise compare ammonia with gold(III) chloride for A-class examples). With compounds such as yttrium barium copper oxide that have one major application that dominates, the page will be likely to focus on that, and there is probably comparatively little known about aspects outside that. Such "one use" compounds are very difficult to assess. Walkerma 18:20, 1 November 2005 (UTC)

Thanks for taking a look at them! I'm not sure that it's really grade inflation that's the problem here, more the fact that our grade criteria have beome clearer over the months. You can take it two ways:

• there are still a lot of not-very-good articles out there (some of which have Physchim62 (talk·RfA) as the one and only editor);
• there is a lot more information on these pages than there was just a few months ago.

Both of these statements are true, needless to say! Physchim62 (talk·RfA) 06:16, 2 November 2005 (UTC)

• The Start/Stub distinction is difficult. To show that, I agree with the four downgradings but for the CaCO3. But better than putting effort in re-assessing (downward) would be to add a little something to the article in question so that Start is better acceptable: enhance the table to completeness, or add a little text. In my count just one good chembox or section already warrants Chem Start, two-four complete sections is B-Class and all (approx 6) sections is A-Class. Wim van Dorst 21:29, 2 November 2005 (UTC).

Template discussion

Hi - you use a template on your organisation page catted {{Chem Stub}}, designed to add the word "stub" to the tables you have there. There is a discussion underway at WP:SFD#.7B.7BStub-Class.7D.7D_.28no_category.29 which directly affects this template, and which we would value your input on. In summary:

• a virtually identical template is being used by the Wikipedia:Version 1.0 Editorial_Team;
• neither your template nor theirs are actually stub templates, although they are named as such;
• your template has an unnecessary category link which means that your organisation page is listed as a stub;
• if your template had no category link, then it would be usable by any wikiproject that wanted to use it (and could make the Version 1.0 one redundant);
• ideally it should also be renamed to something not containing the word stub.

Your opinions are welcomed! Grutness...wha? 03:42, 5 November 2005 (UTC)

It is merely a table aid to indicate that an article is Stub, similar to {{Chem Start}}, {{Chem B-Class}} and {{Chem A-Class}}. The offending category link has been removed now, and there is not controversial issue anymore. Thanks for pointing out that something needed to be fixed. Wim van Dorst 12:57, 5 November 2005 (UTC).

I apologise for causing problems here, my WP1.0 template is a blatant copy of the Chem one, but it was marked for deletion principally because it had no category. I wanted a set of templates we could use for any article, knowing that people would feel odd using a Chem Stub template in their table of history articles. You can see the templates in use on the WPv1.0 project (for example here as well as by the Business & Economics WikiProject. Sorry for causing so much trouble! Walkerma 17:42, 5 November 2005 (UTC)

• Here too, no apologies are necessary. The problem was just a misunderstanding: due to the name starting with Stub, people mistakenly thought it was a Stub template as normally used in main text, which require a category. Hence the probably intentional choice {{Chem Stub}} for our lowest designation. Wim van Dorst 18:53, 5 November 2005 (UTC).

• I can't remember which of us implemented that bit! If it was me, there is a fair chance that it was intentional, and a fair chance that it wasn't! Never mind, I don't fancy going through the tables to change all the templates: maybe the solution is to have fewer stubs... Physchim62 (talk) 12:36, 12 November 2005 (UTC)

Formula elements as links

I have noticed that sometimes the elements in chemical formulas are linked to the element articles. I think this looks confusing because of the underlined characters and it is unnecessary as long as there is a link to chemical formula nearby. The formula is usually only interesting for people which already know how to read the formula, all others should read the article on chemical formulas where the common elements are explained. The only exception could be non-common elements (not C, H, N, O, and S). What do you think. Cacycle 22:46, 5 November 2005 (UTC)

Fully agree. Wim van Dorst 22:56, 5 November 2005 (UTC).

I like having the links, myself; I don't see C₆H₆ as being very much different from m/s². It's at least somewhat helpful to link these symbols directly to their elements — even without following the link, one can pass one's mouse over K and see that it represents potassium. Underlining only strikes me as problematic in situations like C₆H₆, where the numbers become difficult to read. ‣ᓛᖁᑐ 23:12, 5 November 2005 (UTC)

ethylene dichloride or 1,2-dichloroethane

According to our own guidelines, we ought to use the iupac name for the wikipages. But while working on ethylene dichloride (EDC), I encountered a whole group of similarly named C₂-compounds, viz. ethylene (not ethene), ethylene dichloride (not 1,2-dichloroethane), a new ethylidene dichloride (not 1,1-dichloroethane), etc. Outside of the organic chemistry classes, no one would normally say 1,2-dichloroethane to EDC, so the whole article (well, merely Chem Start quality) is written using the colloquial name, or even the abbreviation. Wikipedia guideline (can't find a ref just now) says to use the name as will be normally used to designate a certain subject for the wikipage title. In the chemistry guideline it says systematic name. Now what? POLL: Ethylene dichloride (and equivalents) or 1,2-dichloroethane? Wim van Dorst 08:55, 10 November 2005 (UTC)

• 1,2-dichloroethane. Wim van Dorst 08:56, 10 November 2005 (UTC).

The reference you're looking for is Wikipedia:Naming conventions (chemistry), which states

Generally, article naming should give priority to what the majority of English speakers would most easily recognize, with a reasonable minimum of ambiguity, while at the same time making linking to those articles easy and second nature.

My vote is for 1,2-dichloroethane on the grounds of the ambiguity of ethylene dichloride (However, I prefer ethylene to ethene). Redirects will be necessary (but don't worry, they're cheap!) Physchim62 (talk) 10:49, 10 November 2005 (UTC)

A rule of thumb I've used in the past when starting new articles is that if a traditional name wins the Google poll by a significant margin, then use it; otherwise go with IUPAC. Hence ethylene over ethene. Now, looking at other C₂ compounds, Google says:

• ethylene dichloride: 139,000
• 1,2-dichloroethane: 313,000

• ethylidene dichloride: 25,000
• 1,1-dichloroethane: 686

Shimmin 12:03, 10 November 2005 (UTC)

Following these recommendations, I have moved both ethylidene dichloride and ethylene dichloride to the correct IUPAC names of 1,1-dichloroethane and 1,2-dichloroethane. Thanks for the clear opinions to make this action obvious. PS. I prefer ethene over ethylene. Wim van Dorst 21:08, 10 November 2005 (UTC).

Sorry to be a Johnny-come-lately, but shouldn't those names be 1,2-Dichloroethane and 1,1-Dichloroethane, as described in our naming guidelines? Walkerma 22:13, 10 November 2005 (UTC)

• Oh, No! Who ever thought of that idea? Isn't this counter-intuitive? Nevertheless, I better get a move on, then :-<. Wim van Dorst 22:29, 10 November 2005 (UTC).

I think its counter-intuitive to NOT include the capital in the name! Actually it came out of the lists of compounds, where it was apparent that both forms were used, and we had things like 1,2-dichloroethane (no capital if in mid-sentence!) listed under "1" rather than under "D". Cacycle proposed the idea for capitalisation, and I supported it, it emphasises the start of the word. This is on the grounds that when naming a compound like Chloroethane we capitalise the start of the word in Wikipedia article names, just like in any chemical catalogue. Since all prefixes in chemical names "don't count" (look in any catalogue, even our stockroom list is done this way) when alphabetising, we go to the start of the word part of the name. To do otherwise would go against what chemists are used to. BTW, Wim, thanks for dealing with the objections on the acetic acid FAC page, I was truly impressed by your diligence! Walkerma 22:52, 10 November 2005 (UTC)

• Well, intuitively I hadn't used a capitalized name, nor as any of the numerous already defined wikilinks to the page. It may be a US thing to capitalize all words in a title? It caused me some extra work again. Oh, well. PS. Acetic acid isn't done yet, although the current score of is good (or should that be Acetic Acid ;-]? Wim van Dorst 23:08, 10 November 2005 (UTC).

  No, no! I obviously didn't make myself clear enough in the style guidelines! This is in fact a problem with the wiki software, the first character of an article title is always characterised (as is standard English practice on both sides of the Atlantic). However, for compounds with problem prefixes (such as numerals), to get the title to appear correctly one has to specify the capital as the first letter, and specifically create the redirect from the non-capitalized form... In short, Martin is right. Physchim62 (talk) 10:53, 11 November 2005 (UTC)

  All is OK for these two articles at the present time: the titles are correctly capitalised and the redirects are in place. Acetic acid should stay where it is, with Acetic Acid as a redirect. Physchim62 (talk) 11:13, 11 November 2005 (UTC)

• Yes, I know: a lot of work. Glad that you agree. And my Acetic acid not been done remark is about it not having been promoted to FA yet. Of course capitalisation of Acid would be uncalled for in Acetic acid. Wim van Dorst 20:42, 11 November 2005 (UTC).

I would have a tendency to go with the IUPAC names for 1,2-dichloroethane and 1,1-dichloroethane and even for ethene(changed my mind for consistency with propylene and butylene articles) with redirects from all commonly-used "common names". I remember when I wrote the Benzenediols article, I made a ton of Redirects. However, I agree that the general public and professionals use "ethylene" a lot more than "ethene", so I would understand making Ethylene the main article. However at this point, I'm going to leave in up to you guys. I once wrote the article Ethanoyl chloride (based on the IUPAC name "ethanoic acid") and watched it changed to Acetyl chloride. Maybe there's an even more official IUPAC name for ethanoyl chloride. I do understand that for some compounds, the IUPAC names are horribly unwieldly and are practically never used, except as a note under a more common name. For these, of course, the commonly used names ought to be used for articles (especially including some polymers). H Padleckas 08:31, 13 November 2005 (UTC) H Padleckas 19:14, 15 November 2005 (UTC)

Yet another complication with IUPAC naming is that many names can be written as 1-propanol or propan-1-ol, 2-propanol or propan-2-ol, 1,3-butadiene or buta-1,3-diene, 1-butene or but-1-ene. AOL searches of the pairs including 1-propanol, 2-propanol, and 1,3-butadiene have shown me that the number prefixes at the beginning of the name generate far more hits than names with the numbers in the middle, by ratios ranging 7 - 18 to 1. H Padleckas 12:14, 13 November 2005 (UTC)

Groups of chemical compounds: thiophenols, toluidines

user:H_Padleckas just added thiophenols to the worklist, and while looking at that change I noticed that there is also toluidines in there. Now, both articles are not about a specific chemical compound but more indicate a class of chemicals. I propose to have them replace in the list by the most important compounds out of the group, e.g., Thiophenol (currently redirected back to thiophenols) and p-Toluidine (currently redirected back to toluidines). Same as 1,3,5-Triazine for the triazines. Wim van Dorst 20:51, 11 November 2005 (UTC).

I wholeheartedly agree. I accept that we need a page like carboxylic acid as well as acetic acid, but only acetic acid belongs in one of our lists at present. Likewise thiophenols seems to cover a family of compounds - in principle millions of substances, whereas the building block is that foul-vomit-smelling substance that I grew to love loathe during my time as a grad student (I still went and bought 500 mL last month, though!). Since we already have 35 articles on our list of 30, I think we should remove all non-specific articles. If we need some more building blocks we could consider methylamine and dimethylamine which are important compounds we don't cover at present? Walkerma 22:42, 11 November 2005 (UTC)

Already the para-Toluidine has been created, but as 30 was our target, I'll do some weeding. And you aren't yourself suggesting any table creep here for MMA and DMA, are you, Martin? Wim van Dorst 23:28, 11 November 2005 (UTC).

I would suggest we keep a list of group-of-compound articles somewhere, as this is a problem that keeps coming back. Physchim62 (talk) 12:28, 12 November 2005 (UTC)

I am well on my way to preparing a list of group-of-compound articles offline (finished, see below) with my recommendations on each of the articles. When I created the Toluidines article, I meant to cover the o-, m-, and p- isomers of methylaniline (common names vs. IUPAC issues again  :-/). When I created the Thiophenols article, I intended to cover both (1) the thiophenols class of compounds and (2) the compound thiophenol itself, perhaps eventually adding a Table of Properties to it. I think it would be nice to have a Wikipedia article or articles on these two topics somewhere, although there may not be enough material to write separate articles on topics (1) and (2) above and some may consider that thiophenols or toluidines are not important enough to be on our Building Blocks list. My insertion of these compounds in the BB list was merely like a proposal; you can take them out if you think they are not sufficiently important enough to be on the list. There are separate articles on (a) the compound Phenol and (b) the class of compounds Phenols of which phenol is the skeleton structure; however at this time anyway, those compounds are more widely used and there is enough material for two separate articles. I did not intend to "create more work" for the Chemicals WikiProject by adding those compounds to the list. Also, I never really thought of the number 30 as being a particularly magical number that we must adhere to. H Padleckas 11:15, 13 November 2005 (UTC)

The IUPAC preferred name is toluidine. I'm intrigued as to what you are planning to put in thiophenols regarding "the class of compounds", but I look forward to learning something. As for the parent compound, I once managed to close the Chem Dept for three days with a spillage... Physchim62 (talk) 11:36, 13 November 2005 (UTC)

Maybe we can take the Thiophenols article off the Building Blocks list for now. Adipyl dichloride is a significant industrial intermediate in polymer production, but does not have its own separate article, and I'm not suggesting we create one. It is covered as an example with its own structure pic and mini-industrial discussion under Acyl halides. So I think it's possible to cover certain compounds in their general compound class articles, similar to the way thiophenol is covered in the Thiophenols class article. Not too long ago, I started stubs on Diethanolamine (DEA) and Triethanolamine (TEA). They were added to the "Other important compounds" list. Monoethanolamine (MEA) is definitely important enough to have on this list. Although the other two ethanolamines have applications, I concede they may not be important to make this prestigious list. I'm even thinking maybe someday I'll merge them into the Ethanolamine article. There is still more to be said about monoethanolamine in there. H Padleckas 11:58, 13 November 2005 (UTC)

Here's the list of group-of-compound articles (I alluded to previously above) which I've worked on and off for the past week or so:

Status of some isomer articles and suggestions?? Any suggestions on the individual compound/group articles can be placed right after it.

• Xylene - All three isomers are important and inter-related (although admittedly, from an industrial point of view, para- is most important). All three isomers are in 1 article with a triple Table.

My recommendation: keep it this way. I actually would like to eventually write more on xylenes; there is more to say about them.(HP)

These are really important commodity chemicals, millions of tonnes per year things, they each deserve their own page IMHO. Walkerma 19:13, 15 November 2005 (UTC)

I'm in favour of a single article for the time being, unless someone can convince me that the chemistry of the three isomers is significantly different. Physchim62 15:16, 16 November 2005 (UTC)

• Cresol - All three isomers are equally important. All three isomers are in 1 article with a triple Table.

My recommendation: keep it this way.(HP)

At this point, I agree, a family page is fine. In a year or two we may want to split these.Walkerma 19:13, 15 November 2005 (UTC)

as for Xylenes. Physchim62 15:16, 16 November 2005 (UTC)

• Dicarboxybenzenes (Phthalic acids) - All three isomers are important (although the meta isomer (Isophthalic acid) may be less important than the other two). There are several articles on these by various names - a rather messy situation.

At this time, I don't know what to do about these. (HP)

Again, important commodities, they deserve for each to have their own page. I guess we currently have a transition over to this.Walkerma 19:13, 15 November 2005 (UTC)

I think we need three articles, I will have a go at cleaning up the current situation. Physchim62 15:16, 16 November 2005 (UTC)

• Benzenediols - All three isomers are about equally important. All three isomers are in 1 article and I am preparing a triple Table offline to be added later. There are a couple of independent articles on a couple of these isomers. My recommendation: keep the Benzenediols this way for now, although I concede someday the 3-isomer may be split up into independent articles on each isomer as Wikipedia evolves.

We can live with a common article for now, but within a year I expect us to have separate articles, as they each have their own chemistry. Hydroquinone has all of the quinone chemistry associated with it, resorcinol is the only one where the ring activation is doubled so it has its own chemistry (very common in natural products such as umbelliferone, and catechol is unusual too, forming things like catecholborane and complexes with boric acid.

Separate articles, the chemistry of the three isomers is quite different. Physchim62 15:16, 16 November 2005 (UTC)

The seperate articles already existed, and the redirects were a mess. I have sorted this out now, so we can bask in the glory of Pyrocatechol, Resorcinol and Hydroquinone! Physchim62 (talk) 12:49, 20 November 2005 (UTC)

• Toluidines - All three isomers are about equally important enough to be covered in Wikipedia. All three isomers are in 1 article with a triple Table which I would like to update later. A separate article on the para-isomer has been started.

My recommendation: I favor having one 3-isomer article, but updating the Table eventually. (HP)

At this point, I agree.Walkerma 19:13, 15 November 2005 (UTC)

Weak agree. Physchim62 15:16, 16 November 2005 (UTC)

• Butane and Isobutane - Both are almost equally important. Currently, the article covers n-butane with an n-butane Table only and mentions isobutane as a sideline. A separate stub on Isobutane has recently been started.

My recommendation: Give n-butane and isobutane equal status and make a double Table which includes n-butane and isobutane. Move to article to Butane isomers with redirects coming from all possibilities. Alternatively, there could be two separate rather equal articles, one on each isomer. (HP)

These are both multimillion tonne commodities, with different uses and different chemistry. They should have separate articles. Walkerma 19:13, 15 November 2005 (UTC)

'Twas me who put in the stub for isobutane, to mark off the IUPAC preferred name. Physchim62 15:16, 16 November 2005 (UTC)

OK, let's have separate articles for Butane and for Isobutane. H Padleckas 20:56, 16 November 2005 (UTC)

• 1,3-Butadiene - 1,3-Butadiene or buta-1,3-diene is definitely more important than 1,2-butadiene or buta-1,2-diene. The 1,2-isomer by itself probably wouldn't merit its own article. Currently, the 1,3-isomer is covered in detail with a single Table and the 1,2- is mentioned in passing without a Table.

My recommendation: I favor an article called Butadiene where there is some elementary introductory discussion of both isomers, but mentioning that 1,3-butadiene is far more important industrially and that the rest of the article will effective cover and have a Table for only the 1,3-isomer. Please see the comment to that effect in Talk:1,3-Butadiene. (HP)

I agree, the 1,2 isomer is obscure and doesn't deserve its own page, unless we create a stub to make the 1,3 page simpler. However Henry's suggestion seems very logical to me. Walkerma 19:13, 15 November 2005 (UTC)

Agree. Physchim62 15:16, 16 November 2005 (UTC)

• 1-Propanol and 2-Propanol (or Propan-1-ol and Propan-2-ol) - are almost equally important. Each has its own separate article; the original article I started for both, Propanol, has been separated into 2 separate articles.

My recommendation: Merge the 2 articles into Propanol isomers with a double Table, although it's ok to keep them separate. (HP)

I did the split, so obviously you can see my opinion. These are both really important compounds that could easily have separate A-class articles. Their chemistry is also quite different, their manufacture is by different methods, their uses are different. Keep separate. You are right to point out the name issue, we need to discuss that. Walkerma 19:13, 15 November 2005 (UTC)

We should have separate articles, surely. Isopropanol is the simplest secondary alcohol... Physchim62 15:16, 16 November 2005 (UTC)

OK, let's have separate articles for 1-Propanol and for 2-Propanol. H Padleckas 20:56, 16 November 2005 (UTC)

• Isomers of Butylene - All the isomers are important enough to have an article covering them, although isobutylene is somewhat more important than the others. All 4 isomers are in 1 article and I plan to prepare a quadruple Table offline to be added later.

My recommendation: keep it this way and add a quadruple Table. Most of the discussion on each isomer is common to the others anyway. Alternatively, the article name can be changed to Butylene isomers. The reason I didn't call it Butene isomers is because isobutylene would be methylpropene in IUPAC.

By all means keep a family page, but these are also important commodity chemicals e.g. for making MTBE, and I think we will need separate pages for each isomer in the next year or two. The debate in my mind is whether or not 2-butene needs to have one cis article and one trans article, I'd be OK with a joint page for both isomers there. Walkerma 19:13, 15 November 2005 (UTC)

• Butanol isomers - All 4 isomers are equally important. All 4 isomers are in 1 article without a Table.

My recommendation: keep it this way and add a quadruple Table. Most of the discussion on each isomer is common to the others anyway. (HP)

At this point I think we can keep them together, like we have for amyl alcohol (which has 8 isomers). I think we will need to split this eventually, but it's not too important for now. Walkerma 20:55, 15 November 2005 (UTC)

Four isomers? I think we should have separate articles for n-butanol, s-butanol and t-butanol on the basis of distinct chemistry and uses. Physchim62 15:16, 16 November 2005 (UTC)

4 isomers:

• (1) 1-butanol or n-butyl alcohol
• (2) 2-butanol or sec-butyl alcohol
• (3) 2 methyl-1-propanol or iso-butyl alcohol
• (4) 1,1-dimethylethanol or tert-butyl alcohol

I never heard anybody use the above IUPAC names for (3) or (4) above. Probably iso-butanol and tert-butanol are ok in IUPAC.

What was I thinking of? of course four! In fact, isobutanol and tert-butanol are not OK for IUPAC (although I would still support them as article titles on the common use principle). The radicofunctional names (2) and (4) would pass, (3) should be "isobutyl" not "iso-butyl". Physchim62 (talk) 05:32, 17 November 2005 (UTC)

• Dioxane - The 1,4-dioxane isomer is far more important than the 1,2- and 1,3-dioxanes. The Dioxane articles mentions and has a chem. structure pic for all three isomers, but after an elementary introduction on all three covers and has a Table for only 1,4-dioxane.

My recommendation: keep it this way. (HP)

I agree, at least for now. Walkerma 20:55, 15 November 2005 (UTC)

I cannot see the logic behind having 1,2-dioxane and 1,3-dioxane on the same page as 1,4-dioxane: we are proposing to discuss a peroxide, an acetal and an ether in the same article simply because they have similar names? Physchim62 15:16, 16 November 2005 (UTC)

• Triazine - There is an an article on triazines as a class of compounds based on substituted analogs of the three triazine isomers: 1,2,3-triazine, 1,2,4-triazine, and 1,3,5-triazine (or s-triazine, deemed to be the more important of the three). A separate article on 1,3,5-triazine has been started. The structures of all three triazine isomers are almost equally important because they are the skeleton structures for a variety of biocides, so Wikipedia should show all three structures somewhere. The three triazines in themselves are not very prevalent as end products as far as I can tell, so Tables of Properties for all three are a low priority.

My recommendation: maybe we can keep things the way they are. (HP)

I agree. Walkerma 20:55, 15 November 2005 (UTC)

So do I. Physchim62 15:16, 16 November 2005 (UTC)

• Ethanolamine, often called monoethanolamine (MEA) to distinguish it from diethanolamine (DEA) and triethanolamine (TEA). There has long been an article on MEA which covered some important consumer uses for it, but no Table yet. There is another industrial use for MEA I would like to expand the article with some day, so there should definitely be a full article on MEA. A while ago, I made and uploaded separate chem. structure pics of all three compounds. I saw some red links to the DEA and TEA compounds and I have started stubs on Diethanolamine and Triethanolamine, adding my previously uploaded pics to them. DEA and TEA have some use, but are not as important as MEA.

My recommendation: I am now thinking I should merge the DEA and TEA articles into Ethanolamine, but have the article effectively cover only MEA in any detail and have a Table for only MEA, but mention DEA and TEA and, near the end of the article, include their structure pics.

Since we have separate articles on DEA and TEA at this point, I think we should leave them and try to expand the stubs a little.

I don't think the stubs are hurting anyone where they are. Physchim62 15:16, 16 November 2005 (UTC)

OK, I'll keep the MEA, DEA, and TEA articles separate. H Padleckas 20:56, 16 November 2005 (UTC)

Have I left any out? Judging from certain comments made since I started working in this list, I'm afraid I suspect some of my recommendations may get a chilly reception.  :-/

I think there are dozens, even hundreds not mentioned! Butyllithium comes to mind, but there are many, many more. Walkerma 20:55, 15 November 2005 (UTC)

In many of the cases of related isomers, much of the discussion is very similar and it would be redundant to have the same similar discussions in 2 or 3 separate articles, but it can be done. Splitting up some of these multi-compound articles may result in short, stubby, rather repetitive, single articles. Separate single Tables of Properties can be made for each isomer, to be put in separate articles. A benefit of having a double or triple Table is that the properties of the isomers (compounds) can be compared side by side. However in this day and age, printouts of separate pages can be made and compared side by side that way. Some 2 or 3 compound articles may eventually be split up as Wikipedia expands.

Also in many cases, there may be a "parent" compound which has a certain skeleton structure, often a ring or group of rings, whose name serves as the name for a group or class of compounds which have that same skeleton structure but with substitutions on it. I think this should be explained in Wikipedia whenever there is an article on a compound which has an important such group of compounds named after it, such as purines, pyrimidines, thiophenols, dibenzofurans, etc. All three triazine isomers are in this "category." H Padleckas 10:48, 15 November 2005 (UTC)

Yes, this is a recurring problem, I think it's different from the "isomer" problem. Instead of being 2 to 8 compound scenario (a closed problem), it is a 1 plus infinite # compounds scenario (open-ended problem). K and I discussed this problem with indole on my talk page this summer (here). Walkerma 20:55, 15 November 2005 (UTC)

n-Butane or Butane

The vote is open after a recent page move. Note that Isobutane exists as a substub. Physchim62 (talk) 12:28, 12 November 2005 (UTC)

• Butane as per IUPAC, with a dismbig link to isobutane. Physchim62 (talk) 12:28, 12 November 2005 (UTC)

Butane Walkerma 15:07, 12 November 2005 (UTC)

As an active mover, I'm also a pliant mover, readily to bow before people who really know the IUPAC naming conventions. It is back. Wim van Dorst 22:07, 12 November 2005 (UTC).

There are two systems of nomenclature for organic compounds (and likely inorganics as well):

• IUPAC naming system (the official one) and
• a common naming system.

In addition to these, there are sometimes trivial names.

I believe the naming for C₄H₁₀ is as follows:

• IUPAC names are butane and methylpropane for the straight and branched chain isomers, respectively.
• common names are n-butane, standing for normal or straight-chained butane, and isobutane for an alkane isomer that is straight-chained except a terminal n-propyl group is replaced by an isopropyl group.

The common naming system is often used more than the IUPAC naming system.

The two compounds have a lot in common, and probably of roughly equal importance. Previously, a single article covered both of them, with the n-butane being the main compound having its own Table and isobutane being its sidekick without its own Table. Some of the discussion for the two compounds would be very similar if each compound had its own separate article. If it was all up to me, I would have one article giving both compounds about equal importance and have a double Table covering both compounds. I have created a couple of triple Tables of Properties already for cases of closely related isomers, for example: Xylene and Cresol. I was planning to create more such Tables; for example, I am working on a triple Table for the three isomers of Benzenediol offline. Is it the WikiProject Chemical's intention to have separate articles for every chemical compound ? H Padleckas 07:47, 13 November 2005 (UTC)

The link for the names of the butanes is here, and for acetyl chloride (mentioned above) here. Physchim62 (talk) 09:34, 13 November 2005 (UTC)

From Physchim's second link above, it seems the names methanoic, ethanoic, propanoic, and butanoic acids are out of IUPAC terminology and formic, acetic, propionic, and butyric acids are now the official IUPAC names. H Padleckas 10:41, 13 November 2005 (UTC)

They always have been... You have to take care with substituted acids, only acetic can be used as a basis for substituted names (although formic is widely used as a basis as well): hence Propionic acid but 3-Chloropropanoic acid. Physchim62 (talk) 11:06, 13 November 2005 (UTC)

Regarding Henry's (possibly rhetorical?) question, my view is that WP:Chem does aim to have an article on every significant compound. Of course the debate is on the subject of significance! It depends on (a) personal opinion, (b) perspective of the contributor (long term or short term) and (c) the extent of the existing articles. This last variable (c) is of course growing; at present, having separate articles on each isomer of p-toluidine seems a bit much, but in a couple of years time it will probably seem very reasonable. Thanks a lot for listing out all of the family pages up above, Henry, it's been great to have a chance to discuss these.Walkerma 06:10, 17 November 2005 (UTC)

I actually think it's much easier to write a single compound article than a family page, because each compound has specific properties and reactions. My feeling is that I was able to write four articles on the phosphorus(III) halides in only a little more time than it would take to write one big article on those four compounds. IMHO, this is where we want to go anyway, so it saves a lot of time over the longer term (1-2 years). Also, the goals for WP:Chem are for specific compounds – this is not coincidence, because I was the one who conceived the goals. These goals reflect the dire state of compound articles that existed a year ago, but this project has turned things around completely since then. If we want to consider goals on family pages or isomer sets, then we should perhaps discuss this, but at present such pages strictly lie outside our specified goals. I think some family pages like phosphorus halides provide a useful broad perspective and should remain forever, but I regard some like the old propanols page as simply a stepping stone to the individual articles. Certainly our functional group/larger family pages are in dire need of help, and (as PC pointed out) should be part of any future plans and goals. Walkerma 06:10, 17 November 2005 (UTC)

Alkanes

On a related note, where should we draw the line for alkane articles? At present, we have articles for all straight-chain alkanes up to hexatriacontane (C₃₆H₇₄), which seems to me to be overkill! My proposal is to merge all articles from nonane to hexatriacontane into a higher alkanes article, while keeping a seperate article for tetradecane hexadecane (because of its role as the basis for cetane numbers). I am currently working on the hexanes, so watch this space! Physchim62 (talk) 09:05, 18 November 2005 (UTC)

Even if these articles aren't merged, it would be good to have Higher alkanes as an overview. ‣ᓛᖁᑐ 10:20, 18 November 2005 (UTC)

Done. Nonacosane is worth keeping as a seperate article too. Physchim62 (talk) 17:05, 18 November 2005 (UTC)

Higher alkanes is a great idea. Can I suggest that we keep separate articles at least until C₂₀? This is just that fatty acids go this sort of length, and the alkanes are the parents of the systematic names too, twenty seems like a good cutoff. Walkerma 17:54, 18 November 2005 (UTC)

Hmm, I see your point; the problem is that there is very little on most of these pages (with the notable exceptions of hexadecane and nonacosane). Maybe the fatty acid problem is best solved by starting with the articles for the saturated fatty acids C₁₄ to C₂₄. Physchim62 (talk) 07:17, 19 November 2005 (UTC)

I don't see any advantage in removing those articles. I would probably have argued against the effort of creating them in the first place, but once it's already done they aren't doing any harm. Even if they are trivially short and perhaps redundant now, many of them may eventually end up with useful/interesting information on them - such as is the case with nonacosane. Edgar181 12:21, 21 November 2005 (UTC)

Data repositories

I've started Wikipedia: WikiProject Chemicals/Data as a repository of useful web sites for finding physical properties & other info in composing chemical compound articles. Shimmin 17:55, 19 November 2005 (UTC)

• Did you know of Wikipedia:WikiProject Chemicals/Data_book? Wim van Dorst 20:14, 19 November 2005 (UTC).
  • And of the External links section in Wikipedia:WikiProject Chemicals/Style_guidelines? Physchim62 (talk) 08:05, 20 November 2005 (UTC)
    • The extlinks do serve the purpose. The Data book does not, as it is a collect of data, while what I had in mind were links to much larger collections of data. Shimmin 19:57, 20 November 2005 (UTC)
      • This is my first discussion thread edit, so please have mercy on me! Isn't there a couple of articles regarding Chemical_databases, Chemistry_resources and alike info already? I’ve been visiting and editing a bit the Chemical resources and Chemical databases articles, so I see that info is fragmented between those pages and the ones you are proposing right here. Wouldn’t it be better to unify all the chemical resources or info center in a single page?, or at least link al data from one page? Antrax 13:47, 5 December 2005 (UTC)

Transfer from Talk:Methane

Methane entry needs a complete overhall

The information on methane and its presentation is not up to the standard of other articles in Wikipedia.

Much of it is simply unintelligible (perhaps written by people who speak English as a second language?). There are many statements that are, at best, misleading, and at worst complete nonsense, eg: "Methane acts on organic rich shales and produces a minor contribution (1-3%) to form petroleum with true biomarkers as hopanoids and others insaturated hydrocarbons (n-alkenes). Methane interacts with peats, forming coal and bearing mercury, nickel, arsenic,cadmium, selenium, vanadium, uranium and other toxic metals."

Someone with a good knowledge of organic geochemistry AND the English language please should rewrite the entire entry. —Preceding unsigned comment added by 82.83.210.13 (talk • contribs)

I agree. That article is a real mess. However, the article on methane in the German Wikipedia (http://de.wikipedia.org/wiki/Methan) seem to me to be very good (based on my rusty German). That would probably be a good place to start in order to get the English version up to a higher standard. Edgar181 19:05, 21 November 2005 (UTC)

Statistics table

Changes in worklist status between 2005-06-02 and 2005-09-02, all articles grouped
	Grade	From A-Class	From B-Class	From Start	From Stub	From unclassified	New to list
To	A-Class	X	2	1	2	0	2
To	B-Class	6	X	1	2	0	5
To	Start	0	0	X	2	7	6
To	Stub	1	0	0	X	14	15
To	Unclassified	0	0	0	0	X	5
To	Deleted from list	0	0	0	3	5	X

Acetic acid will be on the Main Page on Dec. 1st, 2005

Now that we've worked hard and acetic acid is a featured article, it will be on the main page on December 1st, 2005. I don't know exactly what this will mean for the acetic acid page itself, but I can guess that there will be a LARGE amount of editting to the article that day. I'm guessing that some of the edits will be useful, some will be useless, but most will be vandals. I just want to ask people to keep an eye out for vandalism and useless edits. ~K 08:50, 26 November 2005 (UTC)

• Additionally to all this good and succesful spreading the word of chemistry by good examples, I also put the acetic acid crystals picture on Featured picture candidates. For the first two days, you can add comments only, and after that you are invited to give your support. Wim van Dorst 19:50, 26 November 2005 (UTC).

It was moved to December 2nd, 2005. I can wait. ~K 15:55, 1 December 2005 (UTC)

I see Acetic acid on the English Wikipedia front page now. H Padleckas 01:49, 2 December 2005 (UTC)

Congratulations!

I just wanted to say congratulations on getting acetic acid featured. It's not easy to write featured-quality articles on technical subjects. And I'd like to see more science-related featured articles. Incidentally, we borrowed your organization scheme for WP:MED—good idea! — Knowledge Seeker দ 07:21, 3 December 2005 (UTC)

• Thanks. While browsing for what you did with our worklist scheme, I saw your Trophy Box, and borrowed your good idea back for our WP:Chem. Wim van Dorst 20:43, 3 December 2005 (UTC).
  • I'm glad to see it. Even while keeping track of where to improve, it's important to highlight the progress we've made! Here's to seeing more science articles on the front page! — Knowledge Seeker দ 07:43, 4 December 2005 (UTC)