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    Chemical formulas on Wikidata

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    During a discussion on Wikidata (see https://www.wikidata.org/wiki/Wikidata:Property_proposal/chemical_formula), it came out pages like https://en.wikipedia.org/wiki/C15H20O4 would benefit from the proposal, maybe of interest for people here to add their opinions? AdrianoRutz (talk) 08:40, 29 August 2024 (UTC)[reply]

    {{ping| AdrianoRutz} What exactly is the proposal? These discussions seem to be dominated by editors who have little cred in chemical editing.--Smokefoot (talk) 13:21, 29 August 2024 (UTC)[reply]
    It looks like the proposal is to convert every chemical name into a formula. As shown in the example: 2-hydroxy-5-octanoylbenzoic acid (Q209407), abscisic acid (Q332211), and Santonic acid (Q7420590) will all be changed to be defined as C₁₅H₂₀O₄ (Q129998552). This seems like a bad idea. It's noted in the first comment that the general formula would be "isotope-agnostic", but subclasses could be made for each isotope. Never mind what the implications are for structural isomers. I could be completely misconstruing what the proposal is though because it isn't clear to me either. Looking at it again it appears the proposal is to, instead of defining each chemical's formula as a unique string, defining a specific item for every single chemical formula that can be shared between structural isomers and isotopes. Reconrabbit 15:30, 29 August 2024 (UTC)[reply]
    The proposal is about switching the actual way chemical formulae are modelled internally in Wikidata. Currently, they are strings and not items and this comes with many disadvantages for efficient querying and data redundancy. Having them as items on Wikidata would allow more refined queries (such as "give me all chemical entities that contain X carbon, Y hydrogen and Z oxygen", for example) and drastically reduce the number of "mass" statements needed as these could move from the chemical entity item to the formula item and thus help maintainers focus on less, higher quality masses.
    I will pass above you "street cred" statement. No place for such things, but I invite you to look at the Chemistry project on Wikidata and see the beautiful things some fantastic contributors are doing. AdrianoRutz (talk) 09:33, 23 September 2024 (UTC)[reply]
    This is also highly relevant to Wikipedia, as some existing pages about chemical formulas (https://en.wikipedia.org/wiki/C15H20O4) linked to different chemical entities could heavily benefit from it, or even the chem info box. AdrianoRutz (talk) 09:36, 23 September 2024 (UTC)[reply]

    Made-up chemical names!

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    Hi! I wanted to let you all know of something I came across while browsing today. I removed multiple "alternate names" for very common chemicals that I believe are completely made up, all added in 2023 by the same IP editor:

    None of these names appeared in any legitimate chemical context that I could find aside from a couple of obvious typos, so I went ahead and removed them, but that user has some other questionable naming edits that I wasn't 100% sure about and it seems like there may be others doing the same thing (I think this is likely the same person).

    Thanks, Cystathionine (talk) 07:11, 17 September 2024 (UTC)[reply]

    They would be in the category of WP:Original research. Did any get created as redirects? Graeme Bartlett (talk) 09:03, 17 September 2024 (UTC)[reply]
    The good news is that they're all simple article edits — no redirects — by one or more well-meaning but unhelpful editors (no malicious vandalism). The bad news is that there appear to be other IPs in this cluster. Cystathionine found 42.117.40.173 and 115.74.10.44, and 115.74.4.110 looks like another one. Pattern seems to be edits in early-mid 2023, with no commit messages, by IPs that geolocate to Vietnam (albeit Hanoi and Vũng Tàu, so they might not be exactly the same editor).
    Here's a list of edits from the first two IPs that hadn't been reviewed yet — I'd appreciate if someone else could have a look over my doco here and clean up any remaining mess:
    • Dibenzene in Biphenyl — seems incorrect to me, reverted.
    • Xenene in Biphenyl — valid, kept.
    • Benzoylic acid and Carboxylbenzene in Benzoic acid — both names appear to be rare but valid, kept.
    • Dicarboxylbenzene, Carboxylbenzoic acid, 1,2-Phenylenedicarboxylic acid, Phenylene-1,2-dicarboxylic acid in Phthalic acid — 1,2-dicarboxylbenzene would be valid (but is not what they added), other two aren't really used, reverted.
    • Carbonous acid in Formic acid — not just invalid, but refers to a different compound, reverted; have also removed Isocarbonous acid (added in 13:41, 5 April 2017) as this isn't in PubChem or ChemSpider (or anything else either); could also have added back Aminic acid (rare but valid) but elected not to.
    • Acetocarboxylic acid in 00:43, 3 February 2023 and 00:44, 3 February 2023 (as Acetonoic acid already removed, as well as Acetoic acid, Oxoacetol in 03:39, 4 February 2023 already removed) — invalid, reverted. Also noticed Acetoic acid had been removed from the chembox but not the article body — fixed.
    • Phosphinol in Phosphinous acid — invalid, reverted.
    • Their edits for Lead(IV) acetate and Lead(IV)_chloride actually seem to be OK
    • Plumbous acid in Lead(II) hydroxide — invalid, reverted.
    • Pentylene (and other changes) in Pentene — perhaps technically correct but unhelpful, reverted.
    I haven't had a proper look at the ones in 115.74.4.110 but I think most (though not all) of these need to be reverted too — would someone else be able to have a look over those? Preimage (talk) 14:20, 17 September 2024 (UTC)[reply]
    @Cystathionine Well spotted. ChemSpider and Pubchem both have extensive lists of synonyms for chemical names. If any of the ones the IPs added aren't there, they should certainly be removed and even if they are present in those databases, Wikipedia's chemboxes don't need to include every possible alternate name. Mike Turnbull (talk) 13:16, 17 September 2024 (UTC)[reply]
    Google Patents turns up a couple East Asian patents which Google translates as using "acetoic acid"; compare e.g. TW I462957B  vs US 8952099B2  - though espacenet does not use "acetoic acid" in its own machine-translated version of the Taiwanese patent. As both IP addresses mentioned are from Vietnam, I wonder if this is either a regional form, or a Google Translate issue. In either case I don't think it merits mention on English Wikipedia. Fishsicles (talk) 14:17, 17 September 2024 (UTC)[reply]
    I'd also note that as best I can correlate the two translations, "acetoic acid" does not appear to refer to pyruvic acid, which probably pushes it more in line with a possible MTL issue. Fishsicles (talk) 14:23, 17 September 2024 (UTC)[reply]

    Chembox for a mixture?

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    I wanted to start an article on F-53B, a PFAS mixture mostly used in Asia. It currently does not have a wiki page and since it came up in my masters research (and it is often misused) I thought it would be a good way of putting my degree to use. However, F-53 is a mixture of 2 compounds, one major and one minor. How would I put this in the chembox? Do I make 2 chemboxes, one for the major and one for the minor? Did the Mixbox ever get off the ground?

    I'm still unsure if I can find enough secondary and tertiary sources to actually get the paper off the ground, but I want to hope.

    Speederzzz (Talk) (Stalk me) 13:59, 26 September 2024 (UTC)[reply]

    @Speederzzz A brief search shows this entry in Pubchem and this in Wikidata. These seem to be for F-53B, or at least one of its components. What's the other? My suggestion would be to make the article about that one material (including chembox) and if the minor component is important then place a second chembox later on for it, or just ignore that part. Chemboxes can have multiple components (e.g. see cyhalothrin) but usually only for various notable isomers; I've never seen one for separate substances. doi:10.1016/j.teac.2019.e00066 looks like good review source. Mike Turnbull (talk) 14:26, 26 September 2024 (UTC)[reply]
    Chembox can handle mixtures, with effort, but I wouldn't do so here. Industrial mixtures are prone to change. There seems to be some disagreement as to whether F-53 is a mixture or a pure product (see here) which implies that it might be either, depending on where you buy it. --Project Osprey (talk) 14:43, 26 September 2024 (UTC)[reply]
    You're right, the definitions differ (which caused me much grief during my literature studies). It's one of the struggles I've had in finding a way to formulate the page. Perhaps it would be best to focus on the traits of 6:2 and leave 8:2 for a separate section (with perhaps one mention of the very rarely occurring 10:2). Finding sources on it that aren't scientific papers sadly is still a struggle, although I expect some more attention in the future due to the EU ban that might come to a vote next year (I hope). I still gotta fully look at which sources I can and cannot use here in this corner of wikipedia, but I've had a busy real life that takes precedence. Thanks for the input!
    Speederzzz (Talk) (Stalk me) 22:45, 26 September 2024 (UTC)[reply]
    I feel your pain. It might be worth trying to figure out if it's an intentional blend of 2 or more compounds (which might be done to exploit a synergism, but those details would probably only be in the patent literature), or if it's just a reactor bottoms product (in which case it'll be a huge horrid mess of things). The latter is more common than you might expect (or wish), for instance tricresyl phosphate is effectively a mixture of up to 10 compounds. You biggest problem is that it seems to be used mostly in china, so the literature will mostly be in Chinese. There seems to be some use in the US. The situation in the EU is weird. As best as I can tell it's not ECHA registered, so it shouldn't be possible to use it, but it has been detected in places (here), so it's getting in somehow. If it's not approved in the EU already then the ban wont effect it, so you shouldn't expect any major attention I'm afraid. Project Osprey (talk) 11:22, 27 September 2024 (UTC)[reply]
    I do expect it is an unintentional mixture, seeing how there is a nice series of 6:2 - 8:2 - 10:2 of decreasing percentages that seem probably for a reaction where the one of the reactants is a 2C PFAS, however I have not yet found (and do not expect to ever find) how F53-B is made so I can't be sure. You make a good point on the EU situation, I feel I was a bit too much like this XKCD where I hoped that more attention would be given to all PFAS, but the last time I went to a talk about PFAS the non-expert host did not know the difference PFAS and PFOS. *sigh*
    Speederzzz (Talk) (Stalk me) 11:35, 27 September 2024 (UTC)[reply]
    The synthesis is nightmare fuel. Tetrafluoroethylene and sulfur trioxide react to give a sultone, which ring opens to give a sulfonate-alcohol. More reactions with tetrafluoroethylene and what looks like iodine monochloride (first time I've seen that in an industrial process) give the expected structure except with iodine at the end. The original F53 was made by radical fluorination of this with HF and antimony pentafluoride (truly awful chemistry I assure you - it will slowly chew through your PTFE reactor lining, after which it will rapidly eat through the metal). Seemingly this proved too expensive to make so they switched to F53-B where they displaced with chloride instead. The details are (here), you probably will need to download and open on your desktop so Adobe will know to install the correct character set. I can read not a word of it but the schemes are universal. It confirms low oligomers n=1-4. Project Osprey (talk) 14:06, 27 September 2024 (UTC)[reply]
    It's a shame there is still a barrier between languages for such interesting chemistry. I was suprised by this paper claiming F53 is F(CF2CF2)4OCF2CF2SO3K, being the 8:2 version (8 CF2 on one side of the O, 2 CF2 on the other side). I do remember reading about the fact they used the chlorinated version because of the difference in cost (and seemingly as a loophole in the PFOS ban, since it's almost just as harmful as PFAS).
    Speederzzz (Talk) (Stalk me) 14:40, 27 September 2024 (UTC)[reply]
    Google translate does an OK job. At least you know enough to write a chembox now. For an image show the core structure with appropriate brackets, use indexed parameters to show a mixture of values from the commercial mixture and the dominant isomer depending on what you've got. You know more about it than the regulators now. Project Osprey (talk) 15:02, 27 September 2024 (UTC)[reply]
    Thanks for the review, I should check over my sources from the piece I wrote for my masters on the occurrence and alternatives for PFAS. The idea to write a wiki page on F53-B came partially from my frustration from how unclear the definition of F53-B was. Speederzzz (Talk) (Stalk me) 22:47, 26 September 2024 (UTC)[reply]

    Organic Reactions-sourced articles

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    User:Mevans86 and User:OrganicReactions, probably the same person, were very actively creating articles in 2010. These articles are characterized by many detailed chemical equations (ChemDraw) with yields and conditions. One puzzle: despite the detailed descriptions of the chemistry, the references are bare - no doi's and no titles. That omission really hurts. See Reductions with diimide. It has finally dawned on me that these authors are basically summarizing/transcribing the contents of reviews in Organic Reactions. These editors are copy-pasting references, which also lack doi's and titles (as was typical a few years ago). So now my proposal: almost all of the references in these articles could be replaced with the reference to the parent review. Doing so would accord with policies of Wikipedia, I think. --Smokefoot (talk) 17:04, 4 November 2024 (UTC)[reply]

    Yes, you are right, the reference actually used should be supplied. It is an academic misconduct to pretend that you used a reference that you did not. In the case of our articles, when we write an article we should be checking that the reference actually supports the facts it references, rather than relying on that another writer checked that out. Quite often I find that those references in references do not support the statements. Graeme Bartlett (talk) 22:50, 4 November 2024 (UTC)[reply]

    Good article reassessment for Catalytic triad

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    Catalytic triad has been nominated for a good article reassessment. If you are interested in the discussion, please participate by adding your comments to the reassessment page. If concerns are not addressed during the review period, the good article status may be removed from the article. Z1720 (talk) 17:03, 6 November 2024 (UTC)[reply]

    Radium chlorate

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    Thanks to an issue recently brought to our attention by Nucleus hydro elemon, we had a RfD in pl.wiki and we couldn't confirm any information that was present in our article that was based on Encyclopedia of the Alkaline Earth Compounds by R.C. Ropp. The current text in pl:Chloran radu is everything we could find about this (hypothetical) compound. Maybe it will help you improve your article (and BTW I see that this publication has been added to your article as a source again). Wostr (talk) 22:11, 15 November 2024 (UTC)[reply]

    @Wostr and Nucleus hydro elemon: Why would any editor work on this topic?--Smokefoot (talk) 22:44, 15 November 2024 (UTC)[reply]
    Four hours before @Wostr posted here, a non-specialist editor added the Ropp citation back to radium chlorate. I've just removed it, again leaving us with a completely unsourced article. I think @Wostr is suggesting we should either (1) improve the article using the sources identified by the pl.wiki discussion, or (2) delete the article — the status quo is not acceptable.
    Per the Polish discussion, radium chlorate is mentioned briefly by Gmelin (1977), though not in pure form, only as a 0.5%-1% cocrystal with barium chlorate. They also found a couple of primary sources (e.g. Goldschmidt (1936)) supporting this. I'll leave it to y'all to decide whether this is sufficient to base an article upon, or whether we should delete it (just like we did with Beryllium chlorate, though admittedly this didn't have a Gmelin entry). Preimage (talk) 04:46, 16 November 2024 (UTC)[reply]
    Upon reflection, for highly radioactive elements, it's common to state that compounds exist based on studies of trace amounts (from micrograms down to a few atoms), including cases where they use other compounds as a carrier. Radium's stable enough you don't have to do that, but this observation's making me lean towards keeping the article, provided we improve sourcing and content as suggested. Preimage (talk) 05:51, 16 November 2024 (UTC)[reply]
    Just updated with those additional references. @Wostr, the Polish version of the article might need a slight tweak: Goldschmidt (1936) studied solutions containing 1mg or less of radium salt and 200g of barium chlorate (as well as "1 à 2g de sel" — as far as I can tell, this is sodium chloride, not radium salt) (EDIT: in context, "sel" is actually the barium chlorate seed crystal he's using to initiate the crystallization); he claims Ra/Ba ratios of 10−5 to 10−11 in the solutions (and precipitates) being studied, rather than 0.5–1% as the article currently states. Preimage (talk) 08:21, 20 November 2024 (UTC)[reply]
    Preimage, thanks for clarification. It was my fault. Ra/Ba = 10−5 is correct. Lower ratios refer to other isotops of Ra studied by Goldschmidt. I have corrected this value in pl:Chloran radu. Michał Ski (talk) 18:10, 20 November 2024 (UTC)[reply]

    Probably unrelated, but I want to point out citations like this:

    "Alkaline Earth Hydroxide - an overview | ScienceDirect Topics". ScienceDirect. Retrieved 8 June 2023.

    will also link into that publication. There might be more unreliable sources hiding in articles. Nucleus hydro elemon (talk) 05:32, 16 November 2024 (UTC)[reply]

    For the record, ScienceDirect topic pages are considered "generally unreliable" by WP consensus for several reasons (Wikipedia:Reliable sources/Perennial sources). DMacks (talk) 10:41, 16 November 2024 (UTC)[reply]
    @Wostr and Nucleus hydro elemon: Again, why would any editor write an article on radium chlorate? I am puzzled that when so much is to be done that editors would decide to write on this topic?? Can someone please explain what it is about radium chlorate that encouraged its creation? Do the Polish editors know something that we don't? For example, maybe it played a key role in the isolation/purification of radium? Curie used the technique of coprecipitation, for example. What is worrying is the possibility that we have editors with an urge to create articles on any concoction they dream up. That would be unfortunate, because - surprise, surprise - within Wiki-Chem there are actual needs for article improvement on serious topics.--Smokefoot (talk) 14:48, 16 November 2024 (UTC)[reply]
    Honestly, I don't care at all what you do with this article. We had a problem with it in pl.wiki and your article is in the same form, with the same source. It seemed appropriate to me that since an editor from another project took the time to let us know about this problem, I would do the same and let other projects know. However, since you consider this to be the wrong approach, I will not do it in the future. Wostr (talk) 22:24, 16 November 2024 (UTC)[reply]
    That was not a critisism of your alert here, it applies to the person that wrote the page to start with. Others of us care that the articles are good, and as you point out this is not good, and not supported by any reliable reference. Graeme Bartlett (talk) 04:37, 17 November 2024 (UTC)[reply]
    Reading her doctoral thesis, Skłodowska-Curie doesn't mention chlorates as part of her process, only chlorides. That doesn't preclude chlorate being used in earlier attempts to isolate radium, but it wasn't part of the final published method, and I can't find anything more specific. I'd expect if there were something further available in Polish-language sources, those sources would be cited on pl.wiki. The creator of the en.wiki page seems to have made a large number of stub articles about nonexistent or minor compounds, so I suspect it's just part of that pattern. Fishsicles (talk) 18:46, 18 November 2024 (UTC)[reply]

    I've done some search in Google Books and there's an early 1970s that mentions the use of radium nitrate or chlorate in making luminous dials for watches. Added the source into the article. Graywalls (talk) 02:23, 19 November 2024 (UTC)[reply]

    The World Surface Coatings Abstracts citation might not be as reliable as we would ideally want, as it describes a Japanese patent application — it mentions "Derwent Jap. Pat. Rept.", a reference to the Derwent World Patents Index — and patents often make over-broad claims. Albeit I can't find an exact match: the closest hit on Google Patents was GB1341460A, "Improvements Relating to Luminous Timepiece Dials", issued 1973-12-19, assigned to Suwa Seikosha Kk .
    Your Gmelin citation is fantastic though — that Google Books URL displays the text of the entry in snippet view, which is what we really needed here :) Preimage (talk) 10:51, 19 November 2024 (UTC)[reply]

    Computational chemistry

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    Dejasj and I are having a discussion (polite disagreement) on the external links on Computational chemistry, specifically under the section Specialized journals on computational chemistry and the link to WebMO at the top, are allowed under WP:EL. Ldm1954 (talk) 15:53, 20 November 2024 (UTC)[reply]

    Requested move at Talk:Heavy metal element#Requested move 19 November 2024

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    There is a requested move discussion at Talk:Heavy metal element#Requested move 19 November 2024 that may be of interest to members of this WikiProject. Raladic (talk) 19:17, 26 November 2024 (UTC)[reply]

    Is there a place in Wikipedia to describe the history of atomic weight determination?

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    I think most editors would agree that the convoluted history of the atomic weight of carbon in the 19th century is somewhat notable, but it's only mentioned in passing at the Karlsruhe Congress article. Could we have a more obvious place to describe the controversy (and perhaps weight of some other elements)? 5.178.188.143 (talk) 10:36, 3 December 2024 (UTC)[reply]

    Atomic mass#History points to Dalton (unit)#History, which has a big gap between 1803 and 1898, as well as History of chemistry, the mid-1800s section of which points to Stanislao Cannizzaro and Karlsruhe Congress. Early 1800s concepts of atomic weight are instead covered in History of chemistry#New elements and gas laws. So I think you're right — the early (19th century) history of atomic weight isn't the primary topic of any of these articles. If you can find good references, it might be worth creating a new article to cover it. Preimage (talk) 17:27, 3 December 2024 (UTC)[reply]

    Attribution (alkynylation reactions)

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    Currently, Reppe Chemie and Favorskii reaction both claim the reaction of alkynes with carbonyls to give propargyl alcohols (and related). Who should win here? Project Osprey (talk) 11:15, 3 December 2024 (UTC)[reply]

    Reppe would have turned 13 in 1905, so I imagine Favorskii probably came first. Trofimov (2002) (from the A. E. Favorsky Irkutsk Institute of Chemistry [ru]) states "The base-catalyzed reactions of acetylene and its homologues represent an important part of the classic acetylene chemistry initiated mostly by Favorsky during the two latest decades of the 19th century and then further developed by Reppe, Nazarov and Shostakovsky."[1] From a quick look, it depends what catalyst is employed: Favorskii uses alkali hydroxides (or alkoxides), whereas Reppe uses metal (including alkali) acetylides or other strong bases. Preimage (talk) 12:08, 3 December 2024 (UTC)[reply]

    References

    1. ^ Trofimov, Boris (1 November 2002). "Acetylene and its Derivatives in Reactions with Nucleophiles: Recent Advances and Current Trends". Current Organic Chemistry. 6 (13): 1121–1162. doi:10.2174/1385272023373581.
    Favorskii reaction is my vote. "Reppe chemistry" is (to me) a vague collection of reactions of CO and C2H2 often with metal catalysts. Alkyne trimerization, hydrocarboxylation (C=C + ROH + CO -> HC-C-CO2R), that sorta thing.--Smokefoot (talk) 14:23, 3 December 2024 (UTC)[reply]

    Erosion corrosion of copper water tubes

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    What the Di hydro gen monoxide?! Bearian (talk) 02:41, 8 December 2024 (UTC)[reply]

    Better or worse than Cold water pitting of copper tube? DMacks (talk) 03:24, 8 December 2024 (UTC)[reply]
    I have worked a bit in both tribology and corrosion. Both articles are badly written but definitely relevant topics. I am personally not a big fan of erosion corrosion as an approach, but there are people who use it. As the main article says it is combined tribology and corrosion which can be faster or slower than the two independently for reasons that are not as yet fully understood in many cases.
    I would be inclined to tag both for needing work. I know a few people I could ping to see if they have PhD students willing to improve the articles, but my success rate in such requests is to date terrible. The professional societies should be the people to act, but... Ldm1954 (talk) 13:55, 8 December 2024 (UTC)[reply]

    Good article reassessment of Boron

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    A good article reassessment of Boron has been posted. From what I can see there are a couple of sections, #Boranes and #Organoboron chemistry without sources, although there might be a bit more. Can someone here with boron expertise please add relevant sources -- it's far into my areas of incompetence. Ldm1954 (talk) 14:29, 8 December 2024 (UTC)[reply]

    Stereochemistry and isomers status report

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    In recent weeks some of us have been re-examining our basic articles on isomers. This activity was partly instigated by a homework assignment from UBC. Further propelling my actions was my new-found realization that isomers, practically speaking are separable, and that conformational isomers probably should be considered rotamers, and rotamers probably should not be considered isomers (except when there is some major steric clash). Within the article on rotamers we acknowledge that they could be considered isomers. IUPAC speaks thusly:

    So, stereoisomer and isomer and rotamer (formerly conformational isomer) have been revised, sometimes significantly. Other editors are welcome to review, initiate debate, etc.

    So for the sake of completeness, here are some related articles

    --Smokefoot (talk) 00:25, 10 December 2024 (UTC)[reply]

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