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Question for debate: the role of primary references

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

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

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)

"Compound" terminology

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)

European Commission number

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

Kesarin aroma

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)

US/UK spelling in templates (like Chembox)

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

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

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

Requested article: chemistry societies

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

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

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?

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: "....to 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 http://mol.wmflabs.org 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)

Halorespiration

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

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)

File:Ssssss9.png

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

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 ) -- 67.70.35.44 (talk) 06:20, 7 December 2014 (UTC)

Launch of WikiProject Wikidata for research

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)

Iota Sigma Pi

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

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)

Infobox electrolysis

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)

List of largest chemical producers

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

Imidazole tautomers and numbering system

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)

New articles from a class project

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)

webelements.com

Hi WP Chemistry,

I came across a site when going through the edits of a primarily-spam account: webelements.com. 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)

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

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)

Hello,
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

Structure drawing inquiry

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:
  • Sulfonylurea herbicides
    Sulfonylurea herbicides
  • Triazinylsulfonylurea herbicides
    Triazinylsulfonylurea herbicides
  • Pyrimidinylsulfonylurea herbicides
    Pyrimidinylsulfonylurea herbicides
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

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: http://i.imgur.com/hzC7Bu4.gif ?--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)

Binary compounds of hydrogen

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

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)

Soap v Detergent

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) -- 65.94.40.137 (talk) 04:26, 10 January 2015 (UTC)

Amidicity

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)

Request for comments and suggestions

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!

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

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.". 49.148.118.251 (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)

Is this for real?

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)

A collection of papers in memory of Professor Michael Lappert

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)

Talk pages

It would be a good idea to create a separate importance category for talk pages. 68.47.56.58 (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)

Dicarboxylic acids

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)

3D depiction of aromatic rings

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/Archive 2#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:

  • "Textbook-Integrated Guide to Educational Resources: Aromatic Hydrocarbons: Physical Properties and Sources". Chemical Education Digital Library.
  • "5-allyl-benzo-1,3-dioxole". SpringerMaterials: The Landolt-Börnstein Database.
  • Zoë J. Wood. "3D Molecule". users.csc.calpoly.edu.

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)

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