Wikipedia talk:WikiProject Chemistry

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Discussion of the WikiProject Chemistry - Please add your comment and discussion here. Older discussions are archived.


This discussion page is about the Chemistry project itself, for detailed, in-depth discussions about specific topics, you'd be best served at the talk page of the specific subject, e.g., Chemicals, Chemical infoboxes, etc. There is also an image request page which might be of interest to you.

European Commission number[edit]

What shall we do with this edit/information? --Leyo 01:22, 5 January 2014

Nobody? --Leyo 21:23, 9 January 2014

Question for debate: the role of primary references[edit]

A citation was added to acetamide today (cited 12 times since its publication in the 1930's). This well intentioned action begs the question - which papers should be cited in a Wikipedia article? According to Chemical Abstracts more than 8800 reports discuss acetamide. Is our goal to cite most of the remaining 8799 sources? Here I suggest guidelines for citations in articles on chemical compounds:

  1. stick mainly to reviews and textbooks sources per WP:SECONDARY
  2. lacking good secondary references, use our judgement but be mindful of WP:UNDUE (giving readers impression that an obscure report is a notable)
  3. exceptions include historically big events - compound discovery, Nobel prize winning work
  4. reports of structures (crystalography or electron diffraction etc)

This topic is not easy one, but maybe we can at least discuss it. --Smokefoot (talk) 14:18, 17 October 2014 (UTC)

Agree that it's a sticky topic, hard to make hard-and-fast rules about this sort of thing, because you aren't going to get a lot of secondary sources on scientific topics which are nevertheless interesting and useful for the encyclopedia (and honestly, a lot of mainstream press about science topics is woefully misinformed as it is). My rule of thumb is that secondary sources (including textbooks and I'd even go so far as to say review articles, particularly in major journals) inform what should be actually covered in the article (per WP:UNDUE), and primary sources are used as verification/justification of factual claims; obviously there's some fuzzing that goes on between these two, particularly in highly technical articles.
I don't see a problem adding one or two primary citations to something that already has a secondary source, so long as it's not citation overkill. If you're getting into a really well-cited fact that is covered by hundreds of primary and secondary sources, I'd say it's appropriate to prioritize by citation number and by likelihood of accessibility (i.e. if the paper is available online or open-access, it's probably preferable, all else equal).
Regarding your "exceptions include historically big events", I don't think I follow. Unless you disagree with my above assertion that a limited number of primary sources is OK in addition to a secondary source, then I would think the exception should go the exact opposite way - for stuff that's a big deal, you're likely to have a lot more coverage in secondary sources so you'll be less likely to need to resort to primary sources, and you'd probably just want to cite the original paper as an ancillary, additional citation that is less of a source for factual verification and more a navigational aid. 0x0077BE [talk/contrib] 15:29, 17 October 2014 (UTC)
I would support the idea of (3), the original primary publication of a big find, or the discover of the subject of the article should also be referenced. Our readers are likely to be interested in the original, and not as keen on reports echoing the find. On the topics I have been writing about text books are pretty weak, but at least a mention in a textbook indicates notability. The other difficulty is that most reviews in Chemistry seem to be behind paywalls, and so I do not have access and I will therefore not use them at all. SO accessibility is an important aspect. Professionals like Smokefoot may have easy access and can use Reviews if they wish. Just because a paper gets a reference does not mean that the paper itself is notable, just that it confirms some fact. I think that we do have avoid the speculative writing and overdrawn conclusions that can appear in primary writings, or the press releases put out by universities. However if a secondary reference states the fact and can be found by our writers, then that should be used in preference to the primary reference. Graeme Bartlett (talk) 03:04, 18 October 2014 (UTC)

  • This discussion pops up at regular intervals, attracting the same people and has never reached a worthwhile conclusion.
  1. the definition of a primary source in Wikipedia is confusing: a witness account to a traffic incident and an article published in Nature are both considered primary sources.
  2. A peer-reviewed scientific article should be considered secondary, the primary component is the supplementary info. Publications such as arXiv (not peer-reviewed) are primary
  3. reviews are secondary literature but hardly impartial: all of them written by a leading expert and contributor in that field. Progress in the field discussed is always "important" and "exciting". Ideally a review should be written by someone not related to the field. Do we want the recent history of lets say Russia written by an impartial historian or by Vladimir Putin?
  4. that leaves us with other encyclopaedias. At least written by an impartial author one may hope but libraries do not tend to have more than one such book on a given topic. My library at least does not. Articles demand multiple sources not just one so there is a problem
  5. Is there any challenge or gratification in copying another encyclopedia for generating Wikipedia content? I think not.
  6. a distinction should be made between important general-interest topics such as chemistry where you would not expect to find scientific article citations and specialist topics such as Aldol reaction where you would expect a lot of them
  7. adding scientific article citations and providing links (DOI) is great added value to an article, the easiest way to verify a claim, and in general the abstract is not behind a pay-wall
  8. if you do not allow editors to cite scientific papers then you will never be able to attract new editors.
  9. articles have to be consistent with reviews and textbooks so each article should at least have one of them
  10. we also want to discuss contemporary topics, we should not have to wait two years for a review to appear.

V8rik (talk) 21:08, 20 October 2014 (UTC)

Italicized below is the definition of primary vs secondary sources as it applies to medical research from Wikipedia:Identifying reliable sources (medicine):
  • A primary source in medicine is one in which the authors directly participated in the research or documented their personal experiences. They examined the patients, injected the rats, filled the test tubes, or at least supervised those who did. Many, but not all, papers published in medical journals are primary sources for facts about the research and discoveries made.
  • A secondary source in medicine summarizes one or more primary or secondary sources, usually to provide an overview of the current understanding of a medical topic, to make recommendations, or to combine the results of several studies. Examples include literature reviews or systematic reviews found in medical journals, specialist academic or professional books, and medical guidelines or position statements published by major health organizations.
  • A tertiary source usually summarizes a range of secondary sources. Undergraduate textbooks, lay scientific books, and encyclopedias are examples of tertiary sources.

All Wikipedia articles should be based on reliable, published secondary sources. Apparently few care and others are unhappy or are looking for glory somehow. Given the lack of interest, I'll drop the subject. --Smokefoot (talk) 17:41, 22 October 2014 (UTC)

• Primary sources aren't prohibited or even discouraged in WP:PSTS which says that primary souces can be used but "any interpretation of primary source material requires a reliable secondary source for that interpretation." Use primary sources to document the "big events", use secondary sources to document evaluative claims about the big events, and use tertiary sources to help evaluate due weight for conflicting primary and secondary sources. --Kkmurray (talk) 19:45, 22 October 2014 (UTC)

While it has never been promoted to guideline status, I think WP:SCIRS is relevant to this discussion. PSTS, MEDRS, and SCIRS are largely in agreement that secondary sources are preferred to primary. However, SCIRS is not quite as strident. In the case of medical related articles, despite the medical disclaimer, secondary sources are especially important because of the potential impact of these articles have on peoples lives. In addition, biological results often cannot be repeated and the conclusions of clinical trials frequently contradict each other. Hence the critical need for review articles. In general, results of chemical and physical experiments are generally more repeatable and have less direct impact on peoples lives. Hence the need for secondary sources in the chemical sciences while still preferred is less urgent. Boghog (talk) 20:19, 22 October 2014 (UTC)
Boghog and Kkmurray: Thanks for your well considered comments. Very helpful! The question remains: for a topic that is subject of many publications (often thousands), what is our policy - we should cite articles that tickle our fancy? --Smokefoot (talk) 22:36, 22 October 2014 (UTC)
If we are trying to get the article to featured standard, then we need to go for the best references, which would not normally be the primary reference at all, so the primary should be changed to a tertiary or secondary reference. Otherwise for lower grade articles we can accept reliable references. For notability purposes we should get references written by two different people, but for most Chemistry topics we don't get the problem of independence, unless we get Chemists writing about themselves. Graeme Bartlett (talk) 05:34, 23 October 2014 (UTC)
With regards to Smokefoot’s 4 starting points, I was under the impression that those were the criteria we always aimed for. A lot has already been said about this - but in my experience the major problem is access to journals.
Currently my access to literature is good, so I’m mostly citing reviews but there have been times when I’ve had no access beyond what I can gleam off Google scholar. When that’s been the case I’ve mostly gotten information from the abstracts of papers - and that resulted in me citing mostly primary literature, because reviews don’t give out free information in their abstracts.
There are pages where I’ve done that and not been happy with the results (P3N5, Cl2O) and I should probably go back and review them but I can’t imagine I’m the only one to have done this and I don’t think it’s going to be easy to fix.
Broadly, the ability to find and access reviews on subjects spanning the breadth of chemistry is something you’d only expect in academia or top-tier companies. Of our most active member I’m only aware of 4 academics (Smokefoot, Edgar181, Beetstra, Dmacks), although there may be more. It should therefore come as no surprise that many pages cite a great deal of primary literature.
Smokefoot is right though, this is a problem. There are pages (like the aldol reaction) where we can be expected to employ our common sense about what’s important, but most of the pages we edit are about chemical reaction we’ve never done and chemicals we’ve never heard of. Too much primary and the page can become an eccentric mess (look at the fun we had with Copper hydride). Secondary reviews are essential for good pages because they provide the guidance of someone who is an expert in that area.
However, now that I’ve better defined the problem I still don’t know how we’re going to fix it. Perhaps we can try and use the page ranking system? A page must cite at least 1 secondary ref to get above ‘Start’ class; 2 secondary and 1 tertiary (i.e. a text book) to be ‘A’ class; ‘GA’ or above must have at least 50% secondary/tertiary sources... Something like that, you can debate the boundaries. Project Osprey (talk) 09:14, 23 October 2014 (UTC)
One thing that I think is missing in this discussion is the quality of the citations, regardless if they are primary or secondary. Far too many secondary sources merely describe what has been published in the field with little or no critical commentary. Conversely there are high qualtiy primary sources published in high impact journals that provide a good over view of the field in their introductions. One needs to carefully evaluate the sources one is using. Coverage in a secondary source tends to increase the notability of a primary source, but only if the secondary source provides a critical review of the field. WhatamIdoing said it best: a secondary source is not automatically better than a primary. Boghog (talk) 18:09, 23 October 2014 (UTC)
See WP:NOTGOODSOURCE for an example of me (and others) saying that, and WP:Secondary does not mean independent too, if you're interested in the subject. WhatamIdoing (talk) 15:45, 24 October 2014 (UTC)
  • @Project Osprey: Regarding access to journals, I think that's a side-issue, and an issue of practicality. Presumably you could use a lower-quality, accessible source and drop a {{Verify}} on it, or (if one doesn't already exist), we could create a template that marks sources as needing improvement/augmentation. And, of course, there's always WP:RX. If you think it's a real problem, we could presumably create a sub-page in our namespace for resource exchange, and look into having them transcluded over to WP:RX (either automatically or by bot), that way you could go to say, Wikipedia:Wikiproject Chemistry/Resource Exchange and see all the requests for Chemistry journals/books, but the more general RX people could also step in. 0x0077BE [talk/contrib] 18:59, 23 October 2014 (UTC)
  • You will be surprised how many academics frequent the Wikipedia chemistry pages. But that aside I do not see how featured article status has anything to do with it, small technical articles should be able to attain that level too (with a higher percentage of peer-reviewed scientific articles) but FA has more to do with quantity (we want a big page) than with quality. The aldol reaction page has just two textbook citations and one actual book citation. The other reviews in the list are too specialized to have been of any use. By your criteria the aldol page should no longer be a featured article V8rik (talk) 19:25, 23 October 2014 (UTC)
  • In response to Project Osprey about criteria, our B class and A class assessment is hardly used, and has nothing to say about use of primary references. GA class is independent of this project, so the criteria there cannot be changed. I don't think that we have to specify a proportion, but for A class we may want a check if the references used are the best. For B class they should at least be reliable and not disputed by later reviews. C class should be pretty easy to achive, so any reliable reference should be good. Graeme Bartlett (talk) 21:38, 23 October 2014 (UTC)

Many many mergers[edit]

This project currently has a backlog of around 50 pages with active merge proposals, some of which have been running for years. I was wondering if anyone would be interested in helping me try to resolve some of these. Apologies in advance to our admins if this results in a surge of merger requests.

-yne General chemistry Nonmetal
Acid base buffers High production volume chemicals Norman Edson
Alkyne High Production Volume Chemicals Programme Optical rotation
Autocatalysis Hydride Organofluorine compound
Autocatalytic reaction Hydrothermal liquefaction Peroxyacyl nitrates
Binary compounds of hydrogen InChI Trust Platinum sponge
Blacktop Industrial mixer Propyl
Bufagin International Union of Pure and Applied Chemistry Radiolysis
Butyl Ionic compound S-equol
Carbonaceous Ionic crystal Silicic acid
Car–Parrinello method IUPAC nomenclature of inorganic chemistry Sorption isotherm
Chemistry education Metal Tetraterpenoid
Chromophore Metalorganic vapour phase epitaxy Transition metal oxides
Cohesion (chemistry) Methylene bridge Unhydrolysable glucose polymers
Entropy (energy dispersal) Methylene group Water number
Ethyl group Nomenclature of Inorganic Chemistry Web of Knowledge
Fluoride Non-specific, adsorptive pinocytosis

Regards. Project Osprey (talk) 11:22, 28 October 2014 (UTC)

I merged the two-sentence thing on [[Transition metal oxides]] into our mid-sized oxide. The tidying up of double redirects can be time consuming.

My two cents, --Smokefoot (talk) 13:00, 28 October 2014 (UTC)

Some should be fairly easy and uncontroversial. I merged tetraterpenoid into tetraterpene and redirected InChI Trust to International Chemical Identifier. -- Ed (Edgar181) 13:05, 28 October 2014 (UTC)
Thanks for the help! I think that Hydrothermal liquefaction, Acid base buffers, Sorption isotherm and Blacktop can propably just be deleted or converted to redirects, there's almost no useful content there. I would support merging Carbonaceous into Carbon and -yne into Alkyne. Project Osprey (talk) 13:16, 28 October 2014 (UTC)
I think the Bufagin/Bufadienolide/Cinobufagin/Arenobufagin/Marinobufagin merger is unnecessary. There's a case to be made for the stubs Arenobufagin and Marinobufagin to be merged into Bufagin, possibly, but Cinobufagin is pretty well fleshed out, and the other two have reliable sources and it's not clear to me that they can't be expanded. 0x0077BE [talk/contrib] 14:53, 28 October 2014 (UTC)
The Fluoride/Fluoride toxicity merger doesn't seem necessary either, but I think DMacks has a point that we should probably defer the discussion until after the article's been cleaned up of non-MEDRS-compliant sources. If it doesn't end up being cut down to a stub, it should probably remain separate. My guess is that Wikiproject Medicine, Wikiproject Skepticism and the Fringe Theories noticeboard will probably want to weigh in there to make sure it's not just a haven for fringe theories or a POVFORK of Water fluoridation. 0x0077BE [talk/contrib] 15:02, 28 October 2014 (UTC)

When merges are complete, please don't forget to consider whether corresponding Wikidata items should be merged and, if so, either do that or leave a note here so that I or someone else can do so (or leave a note if you're not sure). Andy Mabbett (Pigsonthewing); Talk to Andy; Andy's edits 09:00, 29 October 2014 (UTC)

Eucaine for your review[edit]

Please help AfC with Draft talk:Eucaine. Chris Troutman (talk) 04:04, 29 October 2014 (UTC)

Draft:Eucaine got copy-paste moved to mainspace by User:Luklear (WP attribution policy/article-rename procedure failure) even after it was flagged by User:Joe Decker as being likely a copyvio/fair-use violation (Luklear then cloned to Α-Eucaine and Β-Eucaine with the same flagged concern still present). I concur with the flagging as being unusable content, though a possibly-viable topic. DMacks (talk) 21:43, 31 October 2014 (UTC)

What is it that you want me to do, to remove the "quotation" and use paraphrasing? Wikipedia still needs a page for β-eucaine because it is clearly a credible and valid encyclopedic entry. It is not like a vague research compound G567938 that was tested on rats. Eucaine has an official name and history of being used on humans. We should not just delete the whole page, but think of ways how it can be edited to meet the standards of wikipedia----Luklear (talk) 03:27, 1 November 2014 (UTC) (talk) 03:25, 1 November 2014 (UTC)

@Α-Eucaine: Half of the article is a quotation, what is everything else as desirable. I am not sure that - even with citation this is allowed in that extent (excess of fair-use). "1900. α β" does not make any sense. Synthesis should have some more words. Structure formula misleading for non-chemists (what is "Bz", "Et",...?). @Β-Eucaine: First sentence does not make any sense. Second sentence even more confusing: beta replaced alpha just because it is "more soluble"? Really, nothing more? "1900. α β", structure and synthesis as above.

→ Conclusion: In that form not useful. --Yikrazuul (talk) 14:11, 1 November 2014 (UTC)
Oh, it's just the latest incarnation of a long-term sock-puppetry problem. Another admin deleted it as such, no need to worry about it further. WP:RBI DMacks (talk) 02:34, 2 November 2014 (UTC)

A collection of papers in memory of Professor Michael Lappert[edit]

A collection of organometallic chemistry papers by Professor Michael Lappert have been published online in his memory by the The Royal Society of Chemistry (where I am Wikimedian in Residence). They will be free to access until October 2015. Andy Mabbett (Pigsonthewing); Talk to Andy; Andy's edits 08:56, 29 October 2014 (UTC)

Free? All I get is a paywall. Axiosaurus (talk) 15:54, 24 January 2015 (UTC)

"Compound" terminology[edit]

I came across a weird bit a phrasing that I'm unsure about. Is it correct to describe a molecular ion (e.g. phosphate: PO4-3) as a "compound"? In my experience it would fine to say that a salt like Na3PO4 is a "compound", but I don't recall seeing that terminology applied to an ion by itself and I wasn't sure about it. It does have a fixed structure, but since it is charged it won't generally exist in isolation as a pure substance. As far as I can tell chemical compound doesn't say anything about electrical neutrality, but I also don't see any examples of ions as "compounds". Dragons flight (talk) 04:12, 3 November 2014 (UTC)

An ion is most certainly not a compound. That needs correcting. Plasmic Physics (talk) 05:54, 3 November 2014 (UTC)
In normal chemistry, ions are generally always countered by a counter ion (to ensure electrical neutrality of the overall system). However, one could argue that when such a salt is in the gas phase, the different ions are 'separate' entities (one would not have discrete NaCl 'molecules' in the gas phase, rather 'Na+' and 'Cl-' ions). For Na3PO4 on could then argue that there would be three Na+ ions, and 1 PO43- ion - the PO43- is then an ion and a 'separate molecule', or 'separate compound' .. but calling it a compound is a stretch (I know some chemists have a magical bottle of electrons in their lab that they add to their reactions .. so they might consider that a compound as well .. ;-) ).
It gets into a semantics question which is difficult to answer properly. I would just suggest to avoid that type of wording - call it a molecular ion or similar. --Dirk Beetstra T C 07:05, 3 November 2014 (UTC)

Kesarin aroma[edit]

There is an article at Articles for Creation with the title "Kesarin Aroma". It would be helpful if a chemistry expert could have a look at it. Cwmhiraeth (talk) 13:38, 14 November 2014 (UTC)

I can't really tell what that article is about. I find no evidence on scholar or google searching that there's anything called "Kesarin" or "Kesarin Aroma". Searching for 2-Hydroxy-4,4,6-trimethyl-2,5-cyclohexadien-1-one to see if there's a common name (much more likely to be notable if it has a common name), it seems like a significant fraction of the article is lifted from or closely paraphrased from this site. If determined to be notable, the Wikitable obviously also needs to be replaced with an infobox, and there are other basic formatting problems (author info, citation style, etc). I'd definitely say decline as is for quality reasons, and decline as non-notable unless the authors can figure out and convey exactly what the article is supposed to be about. 0x0077BE (talk · contrib) 14:32, 14 November 2014 (UTC)
Possibly notable under the name "Lanierone", actually. The 2D chemical structure is likely unattributed copyright infringement lifted from this page. The 3D may be original work, but it's quite low quality. 0x0077BE (talk · contrib) 14:39, 14 November 2014 (UTC)
Lanierone (2-hydroxy-4,4,6-trimethyl-2,5-cyclohexadien-1-one) seems to be notable as a pheromone[1][2] and a volatile component of saffron[3][4] but I couldn't find any sources for "Kesarin aroma." --Kkmurray (talk) 15:14, 14 November 2014 (UTC)
Thank you. I declined the nomination. Cwmhiraeth (talk) 14:12, 15 November 2014 (UTC)
I created Lanierone since it seems notable and I had the refs. --Kkmurray (talk) 22:16, 15 November 2014 (UTC)

Structure drawing inquiry[edit]

Sulfonylurea herbicides.png

Dear Project Chemistry participants,

I don't own ChemDraw. May someone redraw my harvested chemical general formula as SVG? That would be very kind.--Kopiersperre (talk) 19:31, 15 November 2014 (UTC)

What are A, B and X? B is already the symbol for Boron, so it might not be an ideal generic label... 0x0077BE (talk · contrib) 21:31, 15 November 2014 (UTC)
Knowing the context (what article is this for) would help us decide how best to represent the details that are relevant clearly while simply omitting those that are not. For example, "A" and "B" are a common literature way of representing separate sections of a molecule, so that later prose can talk about the "A ring" and the "B ring". But if we're only wanting to talk about this whole class or certain members of it rather than the structural details section-by-section, then specifically labeling the two rings is not necessary at all. DMacks (talk) 21:58, 15 November 2014 (UTC)
Either way, I made three SVG structures:
I didn't include the text from the first one, because there's a preference to be language-independent for these sorts of things, so that they can be reused on other non-English Wikis, so I think the best way to re-create the structure is to explain in the caption what happens when you replace Y with C or N, respectively. I made it with ChemDoodle. I can make changes to it or send anyone the .icl files or export as .cdl files if anyone wants (though it's not like it's hard to make if you have chemical drawing software). 0x0077BE (talk · contrib) 22:18, 15 November 2014 (UTC)
Thanks a lot. By the way commons:Category:Sulfonylureas should be divided in -sulfuron herbicidal and Gli- antidiabetical sulfonylureas.--Kopiersperre (talk) 17:44, 16 November 2014 (UTC)

Second inquiry[edit]

I need your help again, because the german project Chemistry has lost it's best formula drawer.

May someone draw the general structure of Pyrimidine fungicides: ?--Kopiersperre (talk) 23:15, 3 January 2015 (UTC)

Hier bitte:

Substituted pyrimidine

--Smokefoot (talk) 01:25, 4 January 2015 (UTC)

Dear Smokefoot,

could you also draw 5221-53-4 (Dimethirimol)?--Kopiersperre (talk) 11:31, 4 January 2015 (UTC)

BTW: There is also Wikipedia:WikiProject Chemistry/Image Request. --Leyo 01:12, 6 January 2015 (UTC)

US/UK spelling in templates (like Chembox)[edit]

Currently I am improving template {{Engvar}}, a metatemplate (subtemplate). With it, any article editor can enter in a template |engvar=en-UK, and the template shows the word "vapour" not the en-US "vapor". For example, {{infobox element}} uses it, and today the whole article of phosphorus including its infobox is in en-UK as the MoS prefers.

My question is: does anyone of you see any use or need for this in, for example {{chembox}} or {{drugbox}}? -DePiep (talk) 22:35, 15 November 2014 (UTC)


IKA-Works was created by someone with a COI, and it certainly has issues. Can someone with time on their hands have a look, it needs quite some work (especially references showing notability). --Dirk Beetstra T C 03:47, 16 November 2014 (UTC)

Please help review a draft at AFC[edit]

Please see Draft:MXenes and review it for acceptability in mainspace. Roger (Dodger67) (talk) 20:23, 18 November 2014 (UTC)

Requested article: chemistry societies[edit]

I have compiled a list of chemistry organisations, for which we have no article. Andy Mabbett (Pigsonthewing); Talk to Andy; Andy's edits 13:50, 19 November 2014 (UTC)

New or expanded articles[edit]

Inexperienced editors working with me will be or have been contributing to the following articles. If you see anything really awful or weird, please let me know. Here is the list: Bis(cyclooctatetraene)iron, iron boride, cobalt boride, denitrification, chloropicrin, Ziegler alcohol synthesis, green explosives, lead styphnate, methyltrimethoxysilane, laurolactam-cyclododecatriene-nylon-12, 15N NMR spectroscopy, High potential iron-sulfur protein, FeMoco (active site of nitrogenase), transition metal alkyne complex.--Smokefoot (talk) 13:27, 21 November 2014 (UTC)

List of organic compounds[edit]

List of organic compounds was converted to a redirect to Organic compound on 12 November 2011 and the redirect was modified to Dictionary of chemical formulas on 16 December 2011. There was some prior discussion but, as far as I can see, no consensus was reached. I think the argument against List of organic compounds was that it would become impossibly big. I see that Dictionary of chemical formulas has now sprouted some organic compounds so won't this become impossibly big as well? Biscuittin (talk) 12:18, 24 November 2014 (UTC)

In short, yes. We have a lot of random lists like this, mostly dating back to the early days of wikipedia. There is a list-of-lists [[5]]. Some can be kept, some are unworkably broad in scope and should probably be gotten rid of. Project Osprey (talk) 13:52, 24 November 2014 (UTC)
I propose that Dictionary of chemical formulas be restricted to inorganic compounds and that we have a further discussion about what to do with List of organic compounds. The old list still exists in the revision history. Biscuittin (talk) 14:05, 24 November 2014 (UTC)
I have re-instated List of organic compounds for ease of access. Biscuittin (talk) 14:13, 24 November 2014 (UTC)
It would be a pity to delete the list because people have obviously put a lot of work into it. Perhaps it could be split into separate pages by initial letter. Biscuittin (talk) 14:20, 24 November 2014 (UTC)
Just because someone put a lot of work into something doesn't mean it's worth keeping, the two are independent. People lovingly craft extensive fancruft pretty much constantly, and it just tends to bury useful information and create a lot of extra work to maintain. This really feels like something that should be handled using a category instead of a list. 0x0077BE (talk · contrib) 15:29, 24 November 2014 (UTC)
I have created a slimmed-down page at List of organic compounds with hints for inexperienced users to help find the required compound. Is this what you have in mind? Biscuittin (talk) 20:04, 24 November 2014 (UTC)
Absolutely not. All mainspace articles are articles in an encyclopedia. Do not include meta-comments like, "Search in the box in the top right". That's not even an article, it's all just "See also". The lead also refers to what the article used to be. If all the organic compounds are tagged with Category:Organic compounds, then there should be no problem navigating to it. Good list articles tend to be more than a simple navigation page - they contain additional details and prose content. Look at the entries in WP:Featured lists - e.g. List of Interstate Highways in Michigan or even List of Sites of Special Scientific Interest in Cleveland. I think that "List of organic compounds" is likely to have much, much too broad a scope to be a reasonable list article - even one that simply is used as a navigational aid. 0x0077BE (talk · contrib) 22:16, 24 November 2014 (UTC)
I restored the page to its previous status as a redirect to Dictionary of chemical formulas. Personally, I'd rather redirect it to Category:Organic compounds, as Dictionary of chemical formulas suffers many of the same problems as the original list, plus it includes a large number of inorganic compounds. 0x0077BE (talk · contrib) 22:21, 24 November 2014 (UTC)
We need a long-term solution, otherwise Dictionary of chemical formulas will become too cluttered. Biscuittin (talk) 22:31, 24 November 2014 (UTC)

──────────────────────────────────────────────────────────────────────────────────────────────────── I think that Dictionary of chemical formulas has a reason in a way that List of organic compounds does not, because List of organic chemicals is just denoting the binary yes/no "is this part of this class of compounds" - something that can be easily handled by Categories, and as such I think List of organic compounds should redirect to Category:Organic compounds, assuming that mainspace->category redirects are kosher like that.

At least with the dictionary of chemical formulas, it's an attempt to provide a correspondence between names and chemical formulas, so it has some navigational utility. I'm thinking that in the long term, Dictionary of chemical formulas can be replaced by something on WikiData, but I don't fully understand the vision for WikiData's growth, so maybe that's not the right approach. If it remains a list article, it can always be broken up either in some arbitrary way like alphabetically, as List of colors has been, or in a more natural way like "List of chemical formulas by x" where "x" is element, or something like that. Maybe Pigsonthewing wants to weigh in, as he is the Wikimedian in Residence at the RSC, and also, I gather, involved in WikiData in some way. 0x0077BE (talk · contrib) 22:43, 24 November 2014 (UTC)

I agree that the solution to the large article problem is to split it into smaller ones, e.g. List of chemical formulas: A–F or List of chemical formulas: C3–C5, etc. Also, why is it a dictionary and not a list of chemical formulas? --Kkmurray (talk) 23:01, 24 November 2014 (UTC)
I really don't think this is a good idea, the list is far too open-ended, the only criteria are that something be organic and have a formula. There's nothing to stop the list from growing and the end scenario is ridiculous. The Chemical Abstract service currently has more than 90 million chemicals on its books and it’s been estimated that using currently known synthetic methods we could synthesise between 1020 and 1024 different molecules (DOI:10.1021/ci0255782), that's roughly equal to the number of stars in the universe. We really don't have the resources to curate something like that. Project Osprey (talk) 23:16, 24 November 2014 (UTC)

Chemical structure drawing guide -- why is white space required for PNGs?[edit]

Hi, I think that PNGs for 3D structures would fit more comfortably in the drugbox/chembox without white space so I'd like to know why white space is specifically mentioned here in the CSDG: Wikipedia:Manual_of_Style/Chemistry/Structure_drawing#Generating_PNG_files in the first place. Brenton (contribs · email · talk · uploads) 16:40, 26 November 2014 (UTC)

I'm guessing that's just either to prevent clipping or just stylistically people prefer to have a small buffer (though that can and should be added in the markup rather than in the file anyway). Either way, if you're generating new chemical drawings, please use SVG instead of PNG. PNG files will eventually need to be replaced by SVG files anyway. 0x0077BE (talk · contrib) 21:04, 26 November 2014 (UTC)
It would be pretty awesome if ChemDraw could finally add SVG to its OS X version. It's been on their Windows versions for a while now and been available on many other Mac and cross-platform apps for *many* years. On the other hand, some graphics-workshop editors on commons have mentioned that its svg is technically poor. DMacks (talk) 21:22, 26 November 2014 (UTC)
Generally for stuff like that I assume the SVGs are going to not turn out clean, so I clean it up in Inkscape or Illustrator once I export it. It's an extra step, but preferable to uploading a PNG and waiting for someone else to make an SVG of it. 0x0077BE (talk · contrib) 03:56, 27 November 2014 (UTC)
I wonder whether in future it might be possible for Wikipedia (or Wikimedia Commons) to store data about the structure, and then to render it, much like for our MathML rendering? Andy Mabbett (Pigsonthewing); Talk to Andy; Andy's edits 12:57, 27 November 2014 (UTC)
SMILES data (already reported in most infoboxes for chemicals and drugs) is sufficient for autogeneration of a 2D structure. For simple chemical compounds the common algorithms work well, but for compounds that are complex, the output is sometimes confusing, ambiguous, or just plain indecipherable. -- Ed (Edgar181) 13:07, 27 November 2014 (UTC)
Yes, this is correct: " prevent clipping or just stylistically people prefer to have a small buffer". Wnen we standardised our drawing settings, we decided to include a small whitespace border for those exact (aesthetic) reasons. We didn't want pictures posted where the structures could end up rammed up against one another. This standard was loosely based on an earlier standard from User:Cacycle (one of the earliest people on WP to write a lot of organic chem articles); he likewise included a small whitespace border, so I think we kept the same settings as Cacycle. I think we also got the people at ChemSketch (then including Antony Williams) to allow us to create PNG files directly - a new thing then.
I don't see a problem with allowing "borderless" images in Chemboxes, if (a) there are real advantages in doing so and (b) the "border" markup is spelled out in the style guide. However, the current method has the advantage that hundreds of different people - some with minimal WP knowledge - have posted images that look good. For that reason I think it should remain the default, at least for people inexperienced on WP. Walkerma (talk) 14:01, 27 November 2014 (UTC)
Isn't the margin an integral part of a structure image or model in the same way as there is a margin around text on a page or around the motif in a photograph? I don't think that we would ever want a structure or model to touch the box. Cacycle (talk) 19:42, 27 November 2014 (UTC)

@Fuse809: Chemical structures without any whitespace simply look horrible as thumbnails. There needs to be a margin between the structure and the frame.
@Pigsonthewing: Have you seen yet? It's promising, but the quality is currently not the same as for images created using ChemDraw. --Leyo 02:25, 28 November 2014 (UTC)


Someone engaged in research on the topic Halorespiration is adding a lot of information to the article in an unencyclopedic fashion and needs some help. Cwmhiraeth (talk) 12:30, 28 November 2014 (UTC)

I am no expert but halorespiration looks promising, and unlike a lot of the blog-like or COI-based stuff around here, actually is based on real secondary references. The role of alkyl halides as electron acceptors seems like a real topic. Perhaps related to dehalogenation and bioremediation and such.--Smokefoot (talk) 12:51, 28 November 2014 (UTC)
What has been added is not apparent unless you look at the edit side of the page. Cwmhiraeth (talk) 13:25, 28 November 2014 (UTC)

Rfc on terminology on electronic cigarettes[edit]

Members of this wikiproject may be helpful by participating in this RfC about what to use as terminology for the emission from electronic cigarettes. Outside input would be greatly appreciated. Yobol (talk) 20:01, 3 December 2014 (UTC)


Hello chemists, I came across File:Ssssss9.png on Commons, which has a meaningless file name and an equally useless description. All I could determine is that it has something to do with streptokinase. Could someone please take a look at this image and say whether it is worth keeping or deleting, and if kept, what it actually depicts? Thanks, — This, that and the other (talk) 04:23, 5 December 2014 (UTC)

I categorized and renamed the file and added a description. -- Ed (Edgar181) 20:50, 5 December 2014 (UTC)
Thanks! — This, that and the other (talk) 00:42, 6 December 2014 (UTC)

Energy systems/energy system[edit]

There's a redirect at energy system redirecting to an ATP metabolism article. It occurs to me that there are many energy systems, and that this should lead elsewhere or be a disambiguation page. Do we have a general article or would it be energy ? (note also a discussion at talk:energy systems ) -- (talk) 06:20, 7 December 2014 (UTC)

Launch of WikiProject Wikidata for research[edit]

Hi, this is to let you know that we've launched WikiProject Wikidata for research in order to stimulate a closer interaction between Wikidata and research, both on a technical and a community level. As a first activity, we are drafting a research proposal on the matter (cf. blog post). Your thoughts on and contributions to that would be most welcome! Thanks, -- Daniel Mietchen (talk) 02:15, 9 December 2014 (UTC)

New articles from a class project[edit]

There are some recently created chemistry articles that seem to be essays for a class project:

Should these articles be merged into the "parent" articles (Environmental fate and occurrence of carbamazepine --> carbamazepine for example)? I noticed that Iodoacetic Acid as an Emerging Disinfection By-Product was already merged into iodoacetic acid and then deleted. The new content in the parent article could probably use some review and trimming. ChemNerd (talk) 20:16, 11 December 2014 (UTC)

The project seems to be Education Program:Louisiana State University/CHEM 4150 Environmental Chemistry (Fall 2014). How can we best ensure that these new editors are given a warm welcome and encouraged and supported to keep participating? Andy Mabbett (Pigsonthewing); Talk to Andy; Andy's edits 10:27, 12 December 2014 (UTC)

Warm welcome for unsupervised mediocrity??? The record shows that these homework projects do not lead to new editors. The other issue is that the standards in Wiki-chem are such that it is difficult for students in undergraduate classes to contribute meaningfully. --Smokefoot (talk) 14:35, 12 December 2014 (UTC)
Well, per WP:DBN, we're more or less obligated to give them a warm welcome. I'm not familiar with any literature on the matter, but my guess would be that, by and large, new editors are extremely few and far between, and the proportion of people who consistently make high-quality contributions to the encyclopedia is a miniscule fraction of the people who 1. ever make edits to Wikipedia and especially 2. visit Wikipedia. Given that fact, I would guess that it would be very difficult to assess whether or not these Wikipedia Education classes tend to increase participation, and I would guess that even a small increase in the proportion of new high-quality editors can make a big difference.
Either way, probably the articles should be merged up and it might be worthwhile to try to help the instructor if they want to run a similar course in the future. I get the impression that even if these programs are not creating new editors, with a sufficiently good instructor, they may well be useful in providing some "intellectual leverage" and outsource many man-hours of research to his or her students. 0x0077BE (talk · contrib) 15:01, 12 December 2014 (UTC)
In the case of the LSU project, I did contact the "instructor," who explained that she is not really the prof of the course (probably some sort of "coordinator"). We have repeatedly tried over several years to contact the professors of homework projects. The problem is that the faculty also are disconnected from Wikipedia, and one gets the feeling that, after assigning these projects, they just want the kids "to go leave them (= prof) alone". There is an engaged prof from U of MIchigan, whose (grad) students write specialized articles on soft materials that are high level. And there is an emerging set of articles from Texas A&M, e.g. Carbon–hydrogen_bond_activation, the author of which DMacks and I actually managed to influence in terms of some presentation details. In all cases however, these students write large essays, which they drop into an often mature article with little attention to integration. This style of contribution is non-ideal, obviously. --Smokefoot (talk) 15:18, 12 December 2014 (UTC)
I started a merge proposal discussion here for one of the above articles. Your input is welcome. Boghog (talk) 15:33, 12 December 2014 (UTC)
I mean a warm welcome of the kind generously displayed to this new editor, who didn't know how to use talk pages, and was about to "unleash" their students on Wikipedia. Andy Mabbett (Pigsonthewing); Talk to Andy; Andy's edits 16:35, 12 December 2014 (UTC)
The difference is that the prof you refer to did/does the dirty work of curation and, with rare exception, others don't. They assign student essays and run. One could wish that undergraduate homework assignees (i) become active Wikipedians (low probability, as a decade of observation shows) and (ii) be proficient at chemistry (low probability, as a decade of observation shows). (low probablility)2 = tough odds. On top of that recruitment problem, long essays are poorly compatible with the incremental and integrative growth pathway for articles in Wikipedia. It would be wonderful if someone could figure a way to improve the dynamics of these educational projects, and one could expect that editors here would be highly supportive of efforts in that direction.--Smokefoot (talk) 18:46, 12 December 2014 (UTC)
Then the problem in the more recent example is with the educator, not their students who - like anyone, professor, undergrad or lay person - deserves a warm welcome. Andy Mabbett (Pigsonthewing); Talk to Andy; Andy's edits 20:30, 12 December 2014 (UTC)
As an ambassador in residence, you are ideally suited to reach out. In fact, there is a huge need for someone within this project to monitor/coach on these homework projects and to try to get the attention of the instructors. You would be doing the project a great favor. You might consider maintaining a table of projects underway, the authors, the instructor, etc. Would be great. --Smokefoot (talk) 23:17, 12 December 2014 (UTC)
"ideally suited to reach out": As indeed I have done; but it is incumbent on all editors, not just those of us working "in residence", to welcome new editors. The list of projects underway is at: Special:Courses. Andy Mabbett (Pigsonthewing); Talk to Andy; Andy's edits 12:08, 16 December 2014 (UTC)
These sort of courses should have an online volunteer. I actually thought that Wikimedia Foundation did not want them to go ahead without adequate support being available. There is a whole lot of training material for the students. But it does not mean that they use it or learn from it!Perhaps I can volunteer to help, but I can't put in much time at the moment! Graeme Bartlett (talk) 00:23, 13 December 2014 (UTC)
As it stands, the contributions are pretty poor, often off-topic, generally preachy, textbookish, and awfully sourced. It seems unfair for nontechnical "ambassadors" to impose this editing burden on our handful of technical editors. Its about the opportunity cost as well as setting some standards. Oh, well... --Smokefoot (talk) 13:37, 16 December 2014 (UTC)

Comment: Homework assignments are homework assignments, they are not "new editors". These articles are a genuine headache and present numerous problems, as evidenced by the fact that at least three of this bunch have already gone to AfD. If Wikipedia is going to be a repository of homework assignments, we should immediately re-name it Homeworkpedia, and give up all pretenses of being, or even attempting to be, an encyclopedia. Softlavender (talk) 23:26, 23 December 2014 (UTC)

Iota Sigma Pi[edit]

Hello, if anyone has a free moment can you have a look over this article for me - I have put it as a Start-class and I am hoping to get a DYK for it at some point. I only found it through the 'Random Article' button and tried my best to improve it. Thanks ツStacey (talk) 20:49, 16 December 2014 (UTC)

I don't really have a problem with this as a start, but the primary content seems to be a list of awards they give out. Ideally, it would be nice to have a "History" or "Background" section and some description of their other activities; once there's some more content, I'd recommend consolidating the two "awards" sections and probably trimming them down to awards mentioned only in secondary sources (these awards are all sourced directly to their website). In fact, looking at the sourcing, it looks like nearly all of the article is based on primary sources; likely you'll need to find some additional secondary sources talking about ISP before you'll be able to find something that qualifies for a DYK hool. I would also recommend contacting the organization and see if they have any photos they want to furnish that can be uploaded to the Wikimedia commons, maybe something from an event, a photo of the founder, something like that; they may also have a publicity portfolio or some other record of press coverage they've gotten which could help you find sources. Best of luck! 0x0077BE (talk · contrib) 21:57, 16 December 2014 (UTC)
@Staceydolxx: Presumably United States based, but please make that, and the currency used, clear - Wikipedia is an international project. Andy Mabbett (Pigsonthewing); Talk to Andy; Andy's edits 22:01, 16 December 2014 (UTC)
Thank you both for your help! I've added some more info (including History and secondary sources). I will send an email asking for them to upload a photo for the article and any other info. I didn't even think about stating it was in the US, so thanks for your feedback - as I say, I came across the article through Random clicking and I don't have much interest in the subject! ツStacey (talk) 11:10, 17 December 2014 (UTC)

Free 'RSC Gold' accounts[edit]

I am pleased to announce, as Wikimedian in Residence at the Royal Society of Chemistry, the donation of 100 "RSC Gold" accounts, for use by Wikipedia editors wishing to use RSC journal content to expand articles on chemistry-related topics. Please visit Wikipedia:RSC Gold for details, to check your eligibility, and to request an account. Andy Mabbett (Pigsonthewing); Talk to Andy; Andy's edits 12:42, 18 December 2014 (UTC)

Imidazole tautomers and numbering system[edit]

A slightly tricky situation exists with unsymmetrically substituted imidazoles since tautomers are formally different isomers. 5-Nitroimidazole is, for the drug world, the same as 4-nitro isomer (tautomer, I guess). I just redirected 3-Methylimidazole to 4-Methylimidazole , although to a spectroscopist they would be quite different. Does the N gets priority over NH in the numbering? Someone who enjoys heterocyclic chemistry might look through these articles to make sure we have the naming right. We might add statements to the articles about tautomers being equivalent for practical applications. --Smokefoot (talk) 16:54, 20 December 2014 (UTC)

I think 3-Methylimidazole should redirect to 1-Methylimidazole, not 4-Methylimidazole, because the 2-position will always be the carbon between the two nitrogens. When I use the Convert Name to Structure function in ChemDraw, "3-methylimidazole" produces 1-methylimidazole. 5-Methylimidazole should redirect to 4-Methylimidazole because they are tautomers. In general, I don't think we should have separate articles for tautomers (although vinyl alcohol seems like a reasonable rare exception). ChemNerd (talk) 12:40, 23 December 2014 (UTC)
Yes, absolutely on 1-MeIm = 3-MeIm. Will make appropriate changes. --Smokefoot (talk) 12:56, 23 December 2014 (UTC)

Infobox electrolysis[edit]

There are only two articles using {{Infobox electrolysis}}. Do we need it? Is there a better infobox they could use? Andy Mabbett (Pigsonthewing); Talk to Andy; Andy's edits 15:20, 21 December 2014 (UTC)


Just rewrote this article, but I'm curious; does anyone know what azaadamantane-2-on is supposed to be? I don't recognize the -on suffix. Lukeno94 (tell Luke off here) 22:26, 22 December 2014 (UTC)

Should end in "-one", I think. This is the corresponding ChemSpider record. -- Ed (Edgar181) 22:33, 22 December 2014 (UTC)
Probably not a mistake, but obsolete, or German, terminology. See e.g. aceton. Maproom (talk) 11:41, 10 January 2015 (UTC)

List of largest chemical producers[edit]

A new article. Enjoy. Cobblet (talk) 09:29, 23 December 2014 (UTC)

"Specialists often omit such hyphens that are technically required by good English..."[edit]

Some might be interested in the relabeling of Main Group Compound to Main-Group Compound. The change poses no crisis, but there are implications for us specialists since we use language in ways that might not meet the approval of the brain police. Feel free to share your views at Talk:Main-group element#Name improvements. --Smokefoot (talk) 14:39, 23 December 2014 (UTC)

I've requested the page be moved to main group. Please weigh in with your comments. Cobblet (talk) 12:32, 31 December 2014 (UTC)[edit]

Hi WP Chemistry,

I came across a site when going through the edits of a primarily-spam account: To my eye it was easy to see it as another ad-stuffed site that reproduces free content on a particular theme, e.g. randomly chosen page for scandium -- in other words, not to be considered reliable for Wikipedia purposes. But when I did a quick search for the sites added by this user, this one stood out for having a lot of links around, which makes me doubt my assessment. This is not an area I edit much in, so hoping someone here can provide some direction. Thanks! --— Rhododendrites talk \\ 05:55, 24 December 2014 (UTC)

Webelements is one of the original chemistry websites, going back to 1993.[6] I would consider it an acceptable tertiary source. --Kkmurray (talk) 18:25, 24 December 2014 (UTC)

Webelements is a mixed blessing. It no longer appears to be kept up to date. The data page for astatine, for example, doesn't list the recently experimentally established ionisation energy for astatine nor does it have anything to say about recent modelling work predicting that astatine has an FCC metallic structure. I never give Webelements as a source. Instead I check the sources Webelements gives and use one of those, if possible. This doesn't always work. Webelements gives several sources for enthalpy of vaporisation however I wasn't able to confirm the value given by WE for astatine in any of these sources. Caveat emptor. Sandbh (talk) 00:45, 25 December 2014 (UTC)

Ok thanks for the responses. So it sounds like there's no reason to remove the links, but like with any tertiary source if there's a secondary source given, try to get that one instead. --— Rhododendrites talk \\ 16:27, 27 December 2014 (UTC)

One of your project's articles has been featured[edit]

Today's Article For Improvement star.svg

Please note that Dishwashing liquid, which is within this project's scope, has been selected as one of Today's articles for improvement. The article was scheduled to appear on Wikipedia's Community portal in the "Today's articles for improvement" section for one week, beginning today. Everyone is encouraged to collaborate to improve the article. Thanks, and happy editing!
Delivered by Theo's Little Bot at 01:00, 5 January 2015 (UTC) on behalf of the TAFI team

Binary compounds of hydrogen[edit]

I propose to I exchange the periodic table of Kubas complexes in the namesake article for a periodic table of interstitial hydrides/hydrogen (alloys/solid solutions), showing the solubility of hydrogen in the elements at STP conditions, in the form of molar ratios. Such a table would be much more useful, would it not? Plasmic Physics (talk) 23:55, 5 January 2015 (UTC)

Why can't it be in addition? If you do add in such a solution table, make sure there are references right from the start. The non classical hydride table is largely unreferenced, but the information must have come from somewhere. Do you know where? If it is just made up then fair enough, give it the chop. Though two compounds do have a reference. Graeme Bartlett (talk) 07:59, 6 January 2015 (UTC)
In my opinion, it was a poor choice of mine to have included it in the first place, as it does not contribute much to the article, other than taking up space. Of course I can reference it, but I prefer to exchange it. I say that, because as far as I know, none of the complexes listed in that table are stable at STP, and are extremely esoteric. They only prove that given the right conditions, namely MPa-GPa pressure, it is possible to supercharge metals with hydrogen, in the form of undissociated dihydrogen, as the chemistry of molecular hydrides and hydrogen alloys are related. Even so, it does not require an entire table to prove that. Plasmic Physics (talk) 08:40, 6 January 2015 (UTC)
Where in this article is a "Kubas complex" described? I searched the term within the article and did not find it. Complexes are usually some form of coordination compound, and Kubas is not mentioned in these articles. Kubas complexes are defined, at least to specialists, as molecular complexes of η2-H2. At least if one consults his monograph. I just created Kubas complex as a redirect to Dihydrogen complex. Another comment - given the complicated and sometimes controversial edits, it just seems prudent to leave hydride topics alone and put your editing energies to work on other themes. --Smokefoot (talk) 14:15, 6 January 2015 (UTC)
You just answered your own question. The Kubas complexes are described as non-classical hydrides within the article. Plasmic Physics (talk) 20:02, 6 January 2015 (UTC)
  • A Kubas complex is associated with a dihydrogen complex, this is solution chemistry not high-pressure chemistry. The solubility of hydrogen in metals is a worthwhile topic V8rik (talk) 21:08, 6 January 2015 (UTC)
  • The solubility of hydrogen in metals would be a more useful table. My concern with this is that this table is properly referenced from the outset. Regarding Kubas point- the discrete (H2)MHx species found in low temperature matrix isolation studies of transition metals- not classical solvent chemistry Kubas certainly - but there may well be similarities. If structure is the criterion then if/when these were proved to be true η2-H2 complexes it would surely be hard not to acknowledge them as Kubas complexes.Axiosaurus (talk) 10:19, 7 January 2015 (UTC)

OK, so we are in agreement - the article will benefit from the addition of the proposed table. I will proceed with the addition. However, we still have to decide on whether or not to keep the Kubas table, referenced or not. Plasmic Physics (talk) 04:28, 9 January 2015 (UTC)

Experimental drugs[edit]

Do we (or should we) have a policy on experimental drugs? Looking through Chemical pages needing a CAS Registry Number we have a large number of pages like this one. There's a question as to whether we should have pages on unproven drugs at all but my main concern is that something like 90% of drugs fails at some point in the trails system. So we could end-up with a huge number of pages on failed drugs. Should such pages be deleted? If so, should we write a policy we can cite to ease their passage through PROD and other delete processes? --Project Osprey (talk) 16:26, 9 January 2015 (UTC)

I think that we should keep such articles. These articles dont hurt anyone, so long as they dont distract from more useful articles. Some such unused drugs might even prove of interest to future drug designers for all we know. For an example of some intense but apparently high quality editing activity is this area, check out the contributions by the enigmatic User:Medgirl131. --Smokefoot (talk) 18:24, 9 January 2015 (UTC)

Third opinion on the value 3D models[edit]


What purpose does a 3D model serve if it is not space filling? To my mind it is just a duplication of the 2D model in this case, but may obscure some of the bonds if it is not rotating. With a space=filling model at least there use in seeing a clear 3D structure and being able to make a comparison of, for example, possible binding positions. If I am entirely honest I see little use for 3D models at all without the ability to manipulate them, apart from for the aesthetic appeasement of laymen. I am specifically asking because of some of the edits made by Lazord00d (talk) who "justifies" all of his edits with arguments I find difficult to understand as a chemist but apparently make sense to him as someone without "Chemical training". Testem (talk) 18:58, 9 January 2015 (UTC)

Thianthrene is a good example where a ball-and-stick model provides additional information compared to the skeletal formula. --Leyo 20:43, 9 January 2015 (UTC)
Good example. Is that only because it is rigid? Could the same job be done with more functionality by a space filling model? Testem (talk) 20:57, 9 January 2015 (UTC)
In this case a ball-and-stick model is more useful than a space-filling model, especially since the non-planarity can be recognized more easily. --Leyo 17:55, 10 January 2015 (UTC)
Sorry Jynto, As a chemist, I'm extremely surprised by your position on this. I've justified mine with solid logic. If you feel I haven't please feel free to point out where and I'll gladly explain further. To quote myself from a recent post on Testem's talk page: "The blended type of 3d model translates directly from the formulaic model with minimal differences, except that they show atoms that are omitted in the 2d models, therefore they help the broadest range of minds grasp the concept." I do not feel that this logic is flawed.
Laterz Lazord00d (talk) 22:04, 9 January 2015 (UTC)
@Lazord00d: Which omitted atoms do they include? Why is this helpful to a non-chemist? Testem (talk) 11:39, 11 January 2015 (UTC)
My 2 cents, I think that the new images are often not very useful and should be employed selectively. --Smokefoot (talk) 23:30, 9 January 2015 (UTC)
Selectively by what criteria? Point out a standard that makes sense and I'd be willing to adhere to it. Right now in terms of molecular visualization on Wikipedia it's a mish-mash of styles, there is no standard other than butthurt when someone changes something. I've had changes made to my edits before with very reasonable and logical explanations and had no problem with it. The inability of the other players here to provide a point at which I have deviated from what I consider to be sound logic indicates (at least to me) that the drive behind all this has nothing to do with fact or science.. I have explained my position numerous times and asked for explanations of theirs but all I've seen has been almost entirely opinion-based. I've asked for someone, anyone, to explain why or how editing in a manner that, due to the simplicity of the comparison, will allow for anyone to understand is a problem or flawed logic. Thus far I haven't seen any solid response to that. Lazord00d (talk) 23:43, 9 January 2015 (UTC)
IMO selectively in this case would mean a 3D model would only be used where it makes a clear improvement to the understandability of the article, such as with Thianthrene. Testem (talk) 11:39, 11 January 2015 (UTC)
Agreed that 3D images are of limited value, especially of arbitrarily chosen conformations of flexible molecules. The advantage of stick diagrams over space filling is that it is easier to see the underlying connectivity. Space filling may be useful, especially if the surface is color coded by some property like electrostatic potential. Which depiction is better depends on what you are trying to illustrate. Boghog (talk) 23:45, 9 January 2015 (UTC)

@Lazord00d: Are you sure of who you're talking to? Because you seem to think Testem's comment was written by me. @Testem: To answer your question, I think there is a value in ball-and-stick models. They show geometry, and a possible conformation, whereas the skeletal formulas don't. They are also show the scale of the molecule, if not quite as well as their space-filling counterparts. Most importantly the colour-coded spheres are much more intuitive to the non-chemist than zigzag lines will ever be, which I think is the point Lazord00d was trying to get across.

I do think there should be a place for space-filling models too. But it's difficult to draw a line in the sand about when and when not to use them. It's hard to justify a space-filling model when they don't show the bonding, and parts of the molecule are hidden behind other atoms. Making them spin is not the answer, as hard-line academic types like Leprof 2727 are dead set against them, and I must agree. Spinning models are distracting.

So I must turn the question round and ask you, Testem, what advantages do you think space-filling models serve over 'blended' ball-and-stick ones? When should one be used over the other? I'm thinking space-filling for articles with the drugbox template, and ball-and-stick for the regular chemboxes, but I can already see some places where that would not work. And when is it a good idea to use both? Jynto (talk) 23:55, 9 January 2015 (UTC)

To clarify, I question the utility of any 3D models in a majority of articles. An arbitrary display of a single conformation of many is not useful IMO, which is why skeletal formulae are the standard.
Colour coding may appear intuitive at first but unless there is a legend it is not useful to a non-chemist and chemists do not need the additional intuitiveness.
If 3D models must be used then I feel space-filling varieties are of more use as they have some value in at-a-glance comparisons of molecules for receptor binding, but as I say I do not think 3D models are valuable for conformationally restricted compounds.Testem (talk) 11:39, 11 January 2015 (UTC)
Apologies I had some trouble figuring out who was saying what. I'm not always good at stating things in the simplest manner, so sorry if I didn't word things right but Jynto is correct the features he mentioned are why I feel that the blended or stick and ball type models are best for helping even people with no chemistry experience whatsoever understand what they're looking at/reading about. Lazord00d (talk) 01:06, 10 January 2015 (UTC)
@Lazord00d: Why do they help non-chemists understand what they are looking at? Genuine question as it has been a long time since I looked at something from this viewpoint and there may well be a use I am not seeing.Testem (talk) 11:39, 11 January 2015 (UTC)
If I was to answer by a (perhaps quite flawed) analogy, I'd say it's that the difference between skeletal formulas and 3D models is like looking at the blueprints of a car versus seeing a photo of the actual car. Jynto (talk) 01:34, 12 January 2015 (UTC)
Hoping I've interpreted your analogy as you intended: is that beneficial if the person puts no value in the aesthetic qualities of the car and the photo does not visualise anything better than the blueprint? Forgive my constant questions, I am trying to understand my own viewpoint better too. Testem (talk) 09:31, 12 January 2015 (UTC)
I can't think of a better way to say it, but simply put images should look like the thing they're about. Quoted from the Manual of Style:
"Images are primarily meant to inform readers by providing visual information. Consequently, images should look like what they are meant to illustrate, even if they are not provably authentic images." --Jynto (talk) 03:22, 14 January 2015 (UTC)
So then surely we should be using real-colour SEM images? Ball and stick models look nothing like the molecules they represent. You didn't answer my question by linking that :( Testem (talk) 09:08, 14 January 2015 (UTC)

From my perspective the biggest benefits over 2d are the visible presence of all atoms normally omitted in 2d formulaic models, and visualization of angles which, while there is a system of markings in the 2d system to describe them, are much more easily understood visually whenever possible. The more complex the 3d model, the more angles involved, the harder it gets to render in a static 3d image without masking atoms and sometimes whole structures. This applies to both space-filling and ball-and stick models but it's much worse with the former. I've seen rotating .gif models here of both types and dislike them quite a lot, they're distracting and often the axes positions and visual perspective are not optimal. Also, given that Wikipedia is a publicly edited encyclopedia viewed by millions (billions even?), the people who will ultimately view these images in the context of their articles will span an enormous range in every conceivable way. For the majority of them, the most direct comparison between 2d and 3d is what is most helpful for understanding what they are seeing just like the vast majority of people would rather look at the car than it's blueprint. Because this is Chemistry and not cars, the best solution is a blended concept, the stick and ball model. I make mine the way I do because they're most similar to the 2d models and the double-bonds etc correspond directly to the 2d images.

Lazord00d (talk) 16:13, 12 January 2015 (UTC)

I have to say I completely disagree with the idea that ball-and-stick and space-filling models are not useful. The three dimensional structures of molecules are one of their most important characteristics, responsible for many of their physical, chemical and biological properties. Our readers are not simply either chemists or non-chemists, they range from the general public, through school and university students to professional scientists. In general, I find ball-and-stick models more useful as it is clearer which atoms are where - the structure is more open. Their main use is to help readers to visualise the molecules and highlight key structural features such as bond lengths and angles that are not indicated in any great detail in the 2D formulae. Space-filling models give a useful indication of the relative volumes of different atoms, and how closely two or more molecules can pack together.

In a typical Wikipedia article on a molecular organic compound, the skeletal formula is how the molecule is typically depicted in textbooks and journal articles. The drawing conventions can be obscure to the untrained eye, so I began adding 3D models for a wide range of important compounds around 2006. There were a few such images before I began, and now thanks to the efforts of a dozen or so editors there are thousands.

Regarding flexible molecules, yes there are plenty of them, but many important molecules are actually quite rigid - most drugs have a rather inflexible core at least. There is some harm done in conveying the impression that all molecules are static, which they are not, but having the image is probably better on balance than not having one, especially if the flexibility is described in the text.

If you want an idea of how useful and important molecular models are, open a standard undergraduate organic or inorganic chemistry textbook, such as Housecroft's Inorganic Chemistry, and you will see that half the ink is used on them! --Ben (talk) 19:15, 11 January 2015 (UTC)

p.s. In my images, the colour scheme is generally given if you click on the image and go to its description page. You can also work out which element is which colour by comparing the structural formula and the 3D model. --Ben (talk) 19:16, 11 January 2015 (UTC)

For a layman a ball-and-stick model also seems very rigid. Imho 3d models also distort the reality, because atoms are not colorful. When a layman wants to reach higher, he must be able to derive knowledge from the plain old structural formula. Who does really need to know the 3-dimensional structure if he's not a researcher?--Kopiersperre (talk) 11:56, 13 January 2015 (UTC)

I think the answer to that would be 'almost everyone who learns visually'. Some people, possibly including yourself, might just find it very easy to memorise the structures of lots of different compounds, but to almost everyone else, a skeletal formula is a collection of black lines on a white background, and they all look the same. Molecular models are visually distinctive in a way that skeletal formulas are not, which is why readers with visual learning skills can learn the structure of a compound by remembering what it looks like. This also it makes it a lot easier to appreciate the (otherwise quite subtle) differences between compounds, because again molecular models tend to be visualy distinctive from each other. Flat geometry looks very different from aliphatic geometry in a molecular model. An amide group looks very different from a sulfonamide group, and so on. And many readers will associate what they learn about a particular compound with their visual memory of the molecular model they saw on that page.

I'm hoping this doesn't seem entirely foreign to you, because a lot of us are visual learners. Even if you don't learn anything from the model, it is still a tool to assist your learning. It almost doesn't matter whether you're a layman or an expert. The same learning techniques apply. --Jynto (talk) 03:22, 14 January 2015 (UTC)

Pyrrole (left) and 1-pyrroline (right)
Urea (left) and sulfamide (right)
Pyrrole and 1-pyrroline again
And again, urea and sulfamide

I just thought I'd use some images to illustrate my point. Based on what you can see above, you'd never get sulfamide confused with urea if you just remember that it contains the yellow sulfur atom, and urea doesn't. Similarly you wouldn't get 1-pyrroline mixed up with pyrrole if you can remember from the molecular models that it isn't fully planar, whereas pyrrole is. --Jynto (talk) 04:03, 14 January 2015 (UTC)

@Jynto: I do completely understand where you are coming from, and I completely agree that the use of 3D models of any variety is very useful, possibly even essential, in the examples you give. Do you agree though that where the structure is not constrained, the 3D models are much less useful, especially where the conformation conceals one or more parts of the molecule? Testem (talk) 09:03, 14 January 2015 (UTC)
@Jynto: A chemist should think sulf-ur when he hears sulf-amide.
Maybe I'm contaminated by german conservativism. In school we were allowed to play with molecular model sets. In university books you will find some, but not many 3d models.--Kopiersperre (talk) 12:08, 14 January 2015 (UTC)

I don't think anything relevant to this discussion has to do with your country or which way you lean in life ;-). The atoms are all the same.. even German ones. A well-rounded encyclopedia should appeal to users from "school" to the university and beyond. That's why, when I upload a model, it's of the 3d stick-and-ball type that I position as closely to the existing 2d model as possible.

Lazord00d (talk) 17:30, 15 January 2015 (UTC)

Just to let you folks know: I nominated a bunch of inappropriate ball-and-stick models for deletion. --Leyo 01:04, 17 January 2015 (UTC)

Soap v Detergent[edit]

You may be interested in the discussion at talk:dishwashing liquid, as potential names include "dishwashing soap" and "dishwashing detergent" (as there is a chemical difference between the two, I thought you might be interested) -- (talk) 04:26, 10 January 2015 (UTC)

Request for comments and suggestions[edit]

Please take a look at an article I started on chemist inventor William C. Drinkard and provide comments and suggestions. Nolabob (talk) 11:57, 11 January 2015 (UTC)

I've added an infobox to the page, there are a lot of blank fields in its code which could with being populated. He's very much an industrial chemist which in a way will make this harder to write; they don't put out many papers which makes things difficult to verify. --Project Osprey (talk) 10:07, 12 January 2015 (UTC)
Remarkably, he seems absent from search results for VIAF and ISNI. It would be good to see if he does indeed have such an identifier, and if so to add it. Did he perhaps publish under a different name/ initials or a variation? Andy Mabbett (Pigsonthewing); Talk to Andy; Andy's edits 11:29, 12 January 2015 (UTC)
Thats perhaps not surprising, he only published about 11 papers. He's on 30 or more patents though. He does have a scopus Author ID: 16036436000 but it doesn't seem to tie in to any of the independent authour identifier services. Project Osprey (talk) 11:43, 12 January 2015 (UTC)

WikiProject X is live![edit]

WikiProject X icon.svg

Hello everyone!

You may have received a message from me earlier asking you to comment on my WikiProject X proposal. The good news is that WikiProject X is now live! In our first phase, we are focusing on research. At this time, we are looking for people to share their experiences with WikiProjects: good, bad, or neutral. We are also looking for WikiProjects that may be interested in trying out new tools and layouts that will make participating easier and projects easier to maintain. If you or your WikiProject are interested, check us out! Note that this is an opt-in program; no WikiProject will be required to change anything against its wishes. Please let me know if you have any questions. Thank you!

Note: To receive additional notifications about WikiProject X on this talk page, please add this page to Wikipedia:WikiProject X/Newsletter. Otherwise, this will be the last notification sent about WikiProject X.

Harej (talk) 16:57, 14 January 2015 (UTC)

Hardest material[edit]

In superhard material, it states that diamond is the hardest known material. But a neutron star is "a lattice with density about ten thousand times that of terrestrial iron and strength a million times that of steel.". (talk) 15:25, 15 January 2015 (UTC)

You really should use the talk-page at the article for this sort of thing... That said, neutron star material is different and I don't think it really count. It's not hard because of its intrinsic properties, it’s hard because it’s been compacted by massive gravitational forces. Remove the gravity and it wouldn't be very hard anymore, in fact it would probably be the opposite - first a massive explosion as the atomic forces reasserted themselves, then just a cloud of gas. --Project Osprey (talk) 15:42, 15 January 2015 (UTC)
It would remove some room for interpretation to say "hardest known, naturally occurring material". Plasmic Physics (talk) 07:34, 17 January 2015 (UTC)

3D depiction of aromatic rings[edit]

A number of 3D molecular models have recently been added that depict aromatic rings with alternating single and double bonds (example here). Per Talk:MDMA#Image in header, there appears to be a local consensus that in 3D projections at least, alternating single and double bonds is not a sufficiently accurate model of the resonant bonds in the ring. Is there enough support for a "bond and a half" motif such as File:S-MDMA-3D-balls.png to agree that this should be the standard for ball-and-stick models containing benzene rings? Pings follow. Leyo Odysseus1479 Graeme Bartlett Benjah-bmm27 Lazord00d DMacks Sizeofint VQuakr (talk) 03:41, 17 January 2015 (UTC)

  • That looks OK, but do we have a choice to pick from? Another idea is to have template that is some sort of key to explain to the first time viewer what colour is what atom, and what that dashed line means. This would not be part of the image, but part of the image data page. Graeme Bartlett (talk) 08:59, 17 January 2015 (UTC)
  • I think that we ought to have a think about the merits of 3D models and where they are appropriate. The discussion above suggests some agreement that 3D models may be unnecessary and even inappropriate for molecules which are not conformationally constricted. L4zerd00d is obviously keen to contribute but I think that in this case the lack of technical understanding has hindered the utility of these contributions. Testem (talk) 20:42, 18 January 2015 (UTC)
  • I agree that 3D models are not always appropriate to include in infoboxes. When appropriate, I think the 3D representation should be meaningful (e.g., bioactive conformation), clear (easy to see the correspondence between the 2D and 3D structures), and finally aesthetic (eye-candy to draw the attention of readers to the article). Personally I think including dashed lines or valances in a stick figure make it less appealing and I would prefer to see a cleaner look (see for example File:Etizolam pymol 3d.png). If the 2D and 3D structures are drawn in the same orientation and the figure caption includes the color scheme (carbon = grey, hydrogen = white, nitrogen = blue, chlorine = green), I think the correspondence will be clear enough for most people. Boghog (talk) 23:41, 24 January 2015 (UTC)
Failing to indicate bond order (for example in File:Etizolam pymol 3d.png) can be very confusing, even for experienced chemists. There are cases where the bonding situation is ambiguous or complicated, especially in organometallics and complexes, where relaxing the rules is helpful. Benzene rings pretty robust chemical units and it makes sense to depict them with dashed lines - they indicate the bonding, but more importantly, they make the structure simpler to understand at a glance. Alternating single and double bonds are more intricate. Most 3D modelling software automatically introduces dashed lines, so forcing alternating singles and doubles is a faff. The proposed changes would also require a huge amount of redrawing, for no great benefit. I strongly recommend not changing the guidelines. --Ben (talk) 11:29, 25 January 2015 (UTC)
It is not confusing if the 3D depiction is displayed along side the 2D structure. Boghog (talk) 11:52, 25 January 2015 (UTC)
It is also important to point out that MOS are guidelines, not policies where WP:IAR applies. Changing the guideline doesn't require that we redraw all previous structures, just encourages that all future structures are drawn this way for consistency. If someone has the energy to go back and update structures to conform to the present guidelines, that would certainly be OK too if there is consensus. Boghog (talk) 12:05, 25 January 2015 (UTC)
I disagree. Alternating singles and doubles are also very rare in 3D models in textbooks and articles. Any "updating" by a non-expert risks introducing new errors. 2D structures show alternating bonds because they are easier to draw mechanisms with. No-one draws mechanisms with 3D models, hence the discrepancy. --Ben (talk) 12:42, 25 January 2015 (UTC)
I am not sure that I quite follow your last comment. Consensus would require that any changes made are accurate. In addition, removing valances from 3D depictions would tend to decrease, not increase the number of errors. Designating unsaturated bonds in 2D depictions are essential in defining the structure (e.g., cyclohexane vs benzene). Once the structure is accurately defined, then one can understand reaction mechanisms by electron pushing. The depiction of unsaturated bonds in 3D structures may be useful in understanding stereoelectronic effects in reactions. (Again, the most appropriate depiction depends on what you are trying to illustrate.) Boghog (talk) 18:05, 25 January 2015 (UTC)

Perhaps I should have started with this, but regardless here it is: I'd like to begin a discussion on acceptable 3d model construction characteristics. I feel that space-filling 3d models obscure too much detail, and ball-and-stick models that show aromatic rings as a dotted circle inside a ring of atoms, while accurate, do not help readers with zero to little chemistry knowledge relate the images to the 2d skeletal formulae. The 2d fomulae do not depict aromatic rings as a dotted circle, rather they show them as alternating single- and double-bonds. Also, rotating 3d models have been labeled a distraction by others here, and I agree with them: 3d images in the drugbox should be static. I propose that the 3d models be of a construction method that mimics the 2d model wherever possible (except they would include details intentionally omitted in 2d such as Hydrogens), including depicting aromatic rings in the same manner as the 2d structures. The object of this proposal being greater usefulness across the widest range of minds. Also, there is no question in my mind about the utility of having 3d models for every molecule possible. They show detail that the 2d models do not. Lazord00d (talk) 18:25, 24 January 2015 (UTC)

Actually an interior circle in a hexagon is a very common way to draw benzene, ie File:Benzol2 lb 2d.png. I was taught in orgo to only use alternating single and double bonds if I was illustrating a reaction that eliminated the resonance structure. I know others learned it differently, though. I disagree with your suggestion that it is more important to "help readers with zero to little chemistry knowledge relate the images to the 2d skeletal formulae" than it is to be accurate; depiction similar to File:S-MDMA-3D-balls.png seems plenty easy to understand. Why show it wrong when it is so trivial to show it correctly?
As for space filling models, it simply depends what we are trying to show. In File:DNA Furchen.png, we can see the degree of exposure of the major and minor groove - a detail that would be difficult to illustrate with a non-spacefilling model. I agree though the for most molecules, spacefilling is not ideal because of the structural detail that is lost. VQuakr (talk) 19:39, 25 January 2015 (UTC)

I'm not sure it's wrong so much as simply another way of showing the same thing. For example:

All three of which are from educational or professional resources. Also I am not suggesting changing whats already out there, just setting a standard going forward.

Lazord00d (talk) 20:46, 25 January 2015 (UTC)

The 2D structure already defines the bond orders in which case displaying bond orders in the 3D depiction becomes redundant. Boghog (talk) 21:10, 25 January 2015 (UTC)
I also think this whole discussion of Kekulé vs. delocalized bonding is overly pedantic. Both are generally recognized as valid ways of drawing an aromatic structure. We don't need to worry about this subtle distinction in each and every chem infobox. And since bond orders in 3D depictions are redundant, IMHO these can be dispensed with entirely. Boghog (talk) 21:29, 25 January 2015 (UTC)

Yes, actually that's one of the favorable points, is that showing them in the same way helps novices directly translate between the two. Most of the people here in this thread would likely see things similarly to you. My position is that even though it seems redundant to those who have some chemistry knowledge, that redundancy is useful in this case in expanding the appeal and usefulness to even total noobs. You going to have many of them reading these articles whether you recognize it or not. When you're in a certain field and your understanding is deep, it's easy to forget what it was like not to know any of this.

Lazord00d (talk) 21:27, 25 January 2015 (UTC)

Is this for real?[edit]

Someone please take a look at the new article Hlavaty's reduction. I have been completely unable to verify this name, or variants of it, in the literature at Google Books or Google Scholar. Is it for real? Other possibilities: neologism, unfamiliar name for a familiar process, obscure or unpublished process, hoax? I was tempted to nominate it for deletion as unverified, but I thought I had better seek the advice of experts here first. Thanks for any information! --MelanieN (talk) 06:32, 17 January 2015 (UTC)

I should add that my suspicion level was heightened by the name of the editor - a brand new account named User:AdasBadass. --MelanieN (talk) 06:33, 17 January 2015 (UTC)
I have deleted it. Reduction of camphor is by the Meerwein–Ponndorf–Verley reduction giving Borneol. Graeme Bartlett (talk) 09:28, 17 January 2015 (UTC)
Thank you! MelanieN (talk) 09:48, 17 January 2015 (UTC)

Substrates and products merge[edit]

Just a quick post to both WP:MCB and WP:Chem. There are duplicate stub pages for substrate and product. Since in each case one copy just repeats the other I propose that they're merged into substrate_(chemistry) and product_(chemistry) with the biochem-specific parts just as a section.

Discussion on WP:MCB page. T.Shafee(Evo﹠Evo)talk 09:34, 20 January 2015 (UTC)

Talk pages[edit]

It would be a good idea to create a separate importance category for talk pages. (talk) 04:20, 22 January 2015 (UTC)

Why? Plasmic Physics (talk) 10:01, 22 January 2015 (UTC)
I don't think it is a good idea. If that talk page is more important than the page is associated with then just boost the importance rating. This would be a change across all project not just Chemistry. And I suspect the only talk pages like this would be the ones like this one! Graeme Bartlett (talk) 11:46, 25 January 2015 (UTC)

Occupational safety & health[edit]

Hi lovely chemists! User:Smokefoot suggested that I wander by here and let you all know what I've been up to. I'm User:Keilana, the current Wikipedian-in-Residence at NIOSH, the National Institute for Occupational Safety and Health, which is a US federal research agency. I hadn't realized when I went around telling WikiProjects about this collaboration that I'd be writing about chemistry as much as I seem to be - so here I am! I'll probably be mostly working on safety information on various chemicals, especially since NIOSH puts out the Pocket Guide to Chemical Hazards. If there's anything I can do to help you get information about a specific compound, or connect you with researchers and resources, please let me know. And of course, if you have any questions or concerns about my work, my talk page is always open. Cheers! Emily Temple-Wood (NIOSH) (talk) 19:23, 22 January 2015 (UTC)

Emily, welcome and keep asking, although responsiveness at this talk page can be variable. Here is one over-arching comment or even caution, and these comments only reflect my views, not necessarily consensus. The articles on chemicals are intended to be useful to chemists and those interested in learning or using chemistry. All editors know that we could completely overwhelm each of these articles with safety information regarding proper handling and a laundry list of all the consequences of contact with chemical substances (invariably involving some dizziness, nausea, skin irritations, etc). We choose not to summarize all of the safety-tox-consequences. Instead we defer to the MSDS, which we carefully (hopefully) link in every chemical article. This approach is summarized in our style guide Wikipedia:Manual of Style/Chemistry#Safety, which states "The [safety] information in the Chembox is sufficient for most compounds." The exceptions to this approach are chemical species that are acutely toxic (cyanide, etc). Articles on compounds that are in heavy use but are not always acutely toxic, typically also have sections on safety, but usually not long ones. --Smokefoot (talk) 02:48, 23 January 2015 (UTC)
Thanks for the response! I'm obviously coming from a different perspective, but I'm sure we can find a balance. I think that chemicals in heavy industrial use could do with some explanation of their dangers in the workplace, whereas chemicals that you're only going to find in a specialized chem lab are less important. This is definitely a conversation that we can continue to have! Emily Temple-Wood (NIOSH) (talk) 02:56, 23 January 2015 (UTC)
I agree with Emily (and would extend her comment to cover household chemicals). I also think articles on chemicals - and other chemistry topics - are also supposed to be of interest - and useful - to the general readership. Andy Mabbett (Pigsonthewing); Talk to Andy; Andy's edits 09:16, 23 January 2015 (UTC)
I agree with Smokefoot. I read WP articles about chemicals because I want to learn about the chemicals. I don't want the articles cluttered up with a lot of safety information. But I believe that every chemical article should have an easily-found link to safety sheet, preferably in the info box so that potential users of the chemical will know where to look. Maproom (talk) 10:38, 23 January 2015 (UTC)
  • Hi Emily, it’s nice to see someone specifically addressing safety issues, I'm sure that it's something that people are looking for. As Smokefoot points out MSDS's are a good source of information regarding the safety of compounds, however there is a slight issue in that different countries have different regulations, so depending on where on the internet you get your MSDS the hazards may be described differently. For example, as you're U.S. based I assume that NFPA 704 features in your way of looking at things, whereas here in the E.U. we're using the GHS system (which is replacing the ‘R phrases’ and ‘S phrases’ you may be familiar with). The current Chembox is able to support all of these different systems and provides a nice way of listing everything where it won’t get in the way of the main text. If you're going to take that route I would suggest that GHS hazard statements feature in some way as that system was put out by the U.N. and is supposed to be universal. --Project Osprey (talk) 11:35, 23 January 2015 (UTC)
A useful conversation. The following recent edit at dichloromethane seems too (to me at least) generic and completely covered by the MSDS "Symptoms of acute overexposure to dichloromethane via inhalation include: difficulty concentrating, dizziness, fatigue, nausea, headaches, numbness, weakness, and irritation of the upper respiratory tract and eyes. More severe consequences can include suffocation, loss of consciousness, coma, and death." I do not think that Wikipedia needs to tell people that breathing volatile chemicals (aside from noble gases, SF6 and a rare few others ) makes one sick or to detail the nature of the sicknes. Thanks, --Smokefoot (talk) 13:02, 23 January 2015 (UTC)
Smokefoot makes a good point here. Wikipedia does not need to point out the typical hazards associated with exposure to nearly any chemical. This really falls outside the scope of an encyclopedia article. The safety section should focus on potential hazards that are significant, notable, uncommon, unexpected, etc. For the routine safety information we can (and should) provide external links to authoritative resources such as MSDS sheets, occupational health and safety websites, etc. -- Ed (Edgar181) 13:21, 23 January 2015 (UTC)
I'm not clear on that. Breathing in inert gasses like Helium or Nitrogen won't keep you alive, but as long as you also get enough oxygen it won't hurt you either. The symptoms Smokefoot describes seem like they are caused by actual exposure to the chemical, not by just "breathing stuff other than air". It seems similar to the difference between non-toxic, non-caloric substances like aspartame and sucralose (which are not nourishing but also not damaging) and toxic non-caloric foods (which are not nourishing and will hurt you if you eat them). 0x0077BE (talk · contrib) 13:34, 23 January 2015 (UTC) 0x0077BE: I rephrased my remark, thanks for pointing out the noble gas situation.--Smokefoot (talk) 13:41, 23 January 2015 (UTC)
A little information on the pharmacology might not be a bad idea for common (or interesting) compounds, just so long as it follows WP:MEDRS. Regarding DCM I've moved the information of the PEL to the chembox, as there's an option for it. Very few chemboxes contain information of exposure limits - part of this might be because we don't really have the right fields. Currently we only have the options to enter PEL (U.S. centric) and TLV (again U.S. centric and its a safety rather than regulatory value). As we now have a direct line to NIOSH perhaps we could review those options and see if we need to add any new fields? --Project Osprey (talk) 13:37, 23 January 2015 (UTC)
Excessively detailed health and safety information could potentially violate the medical advice prohibition, so handle with care. Roger (Dodger67) (talk) 13:45, 23 January 2015 (UTC)
Thanks for all the input! I really appreciate it. My one concern with linking to the MSDS is that the lay reader may not understand the MSDS. I remember being a beginning chemistry student and having no idea how to read through an MSDS to get what was useful, so I think including basic information could be a good addition in cases where a chemical is widely used industrially. I know that when I'm writing medical articles, I have a lot of trouble remembering that I am writing for the proverbial "smart 15-year-old" and not just doctors and nurses, so things that may seem obvious to me (epinephrine raises your heart rate!) may not be obvious to the lay reader. [[User:Project Osprey}Project Osprey]], I'm happy to go through and add PELs and TLVs to infoboxes as a start. We can also talk to researchers and see what they think we could add - NIOSH also has contacts at other regulatory agencies and we could use those to sort out what other fields could be useful. Again, my hands are tied a bit on the US-centric issue since NIOSH is a US agency and I'm a US-based person, but I think we can sort some of that out. Best, Emily Temple-Wood (NIOSH) (talk) 14:46, 23 January 2015 (UTC)
Forgot to add - I can add PELs but NIOSH doesn't do TLVs, just Recommended Exposure Limits (which would be a very useful thing to add to the chembox) and the short-term exposure limit, which is another useful thing to add. What do you all think about those as parameters? Best, Emily Temple-Wood (NIOSH) (talk) 14:55, 23 January 2015 (UTC)
  • Well, to start with any data is better than no data. I think the idea with MSDS's was to cite them as references and then transcribe the hazard codes into the relevant Chembox section. I'm aware that those codes are a rather 'dry' description of the hazards but they are all defined against the same standards, so when is says 'toxic' rather than 'harmful' that really means something. Regarding the regulatory stuff, I'm not familiar with the current U.S. standard - so it would be good to check that TLV's and PEL's are still the standard values used before starting on that. TLV's are the limit at which things get dangerous, so they're a medical estimate and not a regulatory limit, as such they should be fairly universal (and a lot more useful than LD50) nevermind! If you want to have new fields added to the chembox then you'd be best to raise it at Wikipedia_talk:Chemical_infobox. The other question of course is where do you being? The popular pages list might show you some low hanging fruit. Do you have any particular areas of interest (or assigned goals?) and is there any particular support that you'd like from us? --Project Osprey (talk) 15:24, 23 January 2015 (UTC)
@Project Osprey: Well, I have quite a lot of data! :) TLVs are the toxicology society and RELs/PELs are from NIOSH and OSHA, respectively. So we're good on that! I'll go put something on the chembox talk page to see if people would find the short-term exposure limits helpful as well. I just spoke to some of my NIOSH colleagues and they did say that they will be reaching out to their contacts and collaborators at other OSH agencies around the world to get their guidelines and have them share what would be useful. So watch this space - more international regulatory data (and other data!) will be coming your way! My personal area of interest is carcinogens, but I have pretty free rein on what to work on. So if there's anything that the project is specifically focusing on, or if any editor needs resources, I'm happy to help out. I of course want feedback from everyone and if I contravene guidelines or screw up in some other way, please do let me know. The most helpful thing in the world would be you letting me know what you need! And, thank you so much for your dialogue and comments, it's good to get to know you all. All the best, Emily Temple-Wood (NIOSH) (talk) 16:11, 23 January 2015 (UTC)
Best wishes to you and your colleagues but please dont become too evangelical in your campaign. If you and your colleagues develop a huge amount of content, we can create a new article on Toxicology of DCM or Toxicology of Chlorinated Solvents. We have that pattern of establishing stand-alone safety articles for a variety of important materials - Cyanide poisoning, fluoride toxicity, CO poisoning. But we need to do better than "Symptoms ... via inhalation include: difficulty concentrating, dizziness, ... coma, and death." --Smokefoot (talk) 18:16, 23 January 2015 (UTC)

I agree with Smokefoot and others on this - chemical articles don't need bogging down with a great list of health risks. I do not think that extracting useful information from an MSDS is particularly difficult at all - isn't that the point? With that said, I really respect that a gov organisation is funding adding information to wikipedia and I appreciate that Emily is not the one setting her own job spec. I hope that we can find a pragmatic compromise on our views. Testem (talk) 20:08, 23 January 2015 (UTC)

Comment: I am opposing such unreferenced additions. --Leyo 11:47, 24 January 2015 (UTC)

Easily fixed, providing we agree to accept web-citation from NIOSH. --Project Osprey (talk) 12:07, 24 January 2015 (UTC)
@Leyo: @Project Osprey: My apologies, I didn't know you had to cite stuff in the chembox. Everything I'm adding there comes from the NIOSH Pocket Guide, which seems to be linked in most chem articles. I read through the chembox documentation and the MOSCHEM and it wasn't mentioned, so perhaps that would be something helpful for chem newbies. :) How would you like me to cite the PEL in the chembox? With a normal inline citation or is there some other way you prefer? Best, Emily Temple-Wood (NIOSH) (talk) 00:19, 25 January 2015 (UTC)
There is no PEL_Ref parameter. Should we add this to the Template:Chembox Hazards? If not then inline reference is the way to go. Perhaps we need a template to assist with NIOSH references if there are going to be a lot of links to the same data source. Graeme Bartlett (talk) 00:39, 25 January 2015 (UTC)
+1 --Leyo 00:44, 25 January 2015 (UTC)
I now see there is a Template:PGCH already. Graeme Bartlett (talk) 23:34, 25 January 2015 (UTC)

Dicarboxylic acids[edit]

I have been tidying up dicarboxylic acid and have come across this issue: The sections

Fatty acid carbonates
Phenyl and benzoic alkanoic acids
Fatty acyl-CoA esters
Divinylether fatty acids

do not appear to be about dicarboxylic acids at all. Should this material be transferred to carboxylic acid? I'm not an organic chemist, so I hesitate to do it.

Can anyone help? reply at talk:dicarboxylic acid, please Petergans (talk) 19:54, 25 January 2015 (UTC)


what (hydroxyethyl)methacrylate? (talk) 01:41, 26 January 2015 (UTC)

What are you trying to ask about (Hydroxyethyl)methacrylate? Graeme Bartlett (talk) 03:36, 26 January 2015 (UTC)
it is an anion, what's the cation for the data? — Preceding unsigned comment added by (talk) 04:07, 27 January 2015 (UTC)
No it is a neutral molecule. pKa/pKb is 13.82, so in very alkaline conditions it could lose a proton, or gain a hydroxyl group to make a negative ion. Graeme Bartlett (talk) 11:37, 27 January 2015 (UTC)
The "cation" you're referring to is hydroxyethyl. And the "anion" is methacrylate. That is to say, it is the hydroxyethyl ester of methacrylic acid. But like Bartlett says, it is still a neutral molecule. Hope that clears things up. Jynto (talk) 11:58, 27 January 2015 (UTC)


The usage of Buckyball is under discussion, see talk:buckyball -- (talk) 09:37, 27 January 2015 (UTC)