Wikipedia talk:WikiProject Chemicals#Ethylene (data page)

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An editor has requested for :Alpha hydroxy acid to be moved to another page. Since you had some involvement with Alpha hydroxy acid, you might want to participate in the move discussion (if you have not already done so).

In [https://en.wikipedia.org/w/index.php?title=Flavin_adenine_dinucleotide&curid=1491100&diff=1264708353&oldid=1247491485 edit] this edit], User:Graeme Bartlett says that 3dmet is dead. Indeed, links such as [http://www.3dmet.dna.affrc.go.jp/cgi/show_data.php?acc=B04792] are timing out for me also. Anyone know if this is a transient problem or else if we should remove this infobox item across the wiki? DMacks (talk) 04:20, 23 December 2024 (UTC)

:3DMet has been dead for years now. So I have not been able to confirm any values to add. Since it is dead, our 3dmet links are no longer useful. So I was thinking that I would remove the parameters when I come across them in the chembox. My current effort is to add missing ChemSpider entries. But as I go I might add other values or change wikidata link if wrong, (or remove 3DMet). Back in 2018 I contacted Miki Maeda from National Agriculture and Food Research Organization about 3DMet, But I have not done that since the recent multiyear outage. Graeme Bartlett (talk) 05:51, 23 December 2024 (UTC)

::Sounds like we should turn off its display ASAP (no sense giving readers a broken link). And also set up an editorial note and hidden tracking category for its use (445 pages, by a quick heuristic). Eventually a bot could simply remove them, but for now at least we'll be aware of it when we edit or if someone gets bored and wants to gnome it. DMacks (talk) 05:56, 23 December 2024 (UTC)

:::I did a quick and easily-reversible turn-off of the display,[https://en.wikipedia.org/w/index.php?title=Template:Chembox_3DMet&diff=prev&oldid=1264773621] pending stronger consensus for removing it as a supported template field altogether. DMacks (talk) 12:52, 23 December 2024 (UTC)

::::Time to kill {{tl|Chembox 3DMet}} and remove its fields from the articles? For anyone who deals with wikidata, there is the {{Wikidata property link|P2796}} property. Should it be annotated as being dead somehow? DMacks (talk) 01:50, 20 March 2025 (UTC)

:::::I contacted the developer, Miki Maeda about it. Apparently the Internet available database disappeared in a server migration. It may come back on line within 3 years as it was supposed to be publicly available. Perhaps there are other options such as incorporating the info into Wikidata, but for the next year or so don't expect to see any publicly accessible system for 3DMet. The data is available for individual researcher use on request. Graeme Bartlett (talk) 11:46, 25 March 2025 (UTC)

Just wanted to point out that finally, all the Chemicals articles in the wikiproject have been assessed. You can view the classification in the big chart on the main page. This is essentially thanks to a combination of the automatic classification of set index articles as List-class added to Module:WikiProject Banner Shell, and people manually classifying articles. Just got the last article classified. Mrfoogles (talk) 21:33, 7 March 2025 (UTC)

{{ping|Lamro}} Lamro, do you really think that "Technical Paper. U.S. Government Printing Office. 1917" and "American Druggist and Pharmaceutical Record. ...1895" are good foundations for something (Ammonium oleate) notable? --Smokefoot (talk) 23:16, 7 March 2025 (UTC)

:Actually those sources have substantial content, and would be reliable. But they are not suitable for how they are used, as there is no chemical formula, and they are both on applications of the substance. Graeme Bartlett (talk) 00:26, 8 March 2025 (UTC)

When a new Wikipedia article is created about a chemical, is there any bot or other tool that looks for an existing Wikidata entry for that substance, creates it if not existing, and links the wp article to it? It's not a hard manual task to "look for, and link if existing" (and then flag if need to create). And I'm glad to see a bunch of editors creating new chemistry/drug articles. But that is leaving a lot of missing wikidata links. Would it be useful as a quick step to have chembox (and drugbox too) populate a category for missing wikidata links? DMacks (talk) 14:44, 12 March 2025 (UTC)

:wikidata:User:Pi bot does this, it just takes a while. I've seen it happen on a couple of articles I've created, like Kuicaoxi. Reconrabbit 16:17, 12 March 2025 (UTC)

:When new articles show on the list, and the PubChem entry links to Wikidata then I will link the page to Wikidata. Quite often though there are duplicate Wikidata entries, so I then try to merge. Graeme Bartlett (talk) 23:44, 12 March 2025 (UTC)

Yesterday, a new editor, User:Bram Lentjes and an IP made a very large expansion of the article on VG. These edits raise several issues which I have not followed up in detail (e.g. [https://en.wikipedia.org/w/index.php?title=VG_%28nerve_agent%29&diff=1280620845&oldid=1280613206 use of predatory journal as source]). What I want to discuss first is [https://en.wikipedia.org/w/index.php?title=VG_(nerve_agent)&diff=next&oldid=1280630841 this edit], which introduced a section saying {{tq|We acknowledge the use of AI assistance, specifically ChatGPT, to help paraphrase and refine portions of this text. While the final content was reviewed and edited by our team, AI was utilized to enhance clarity and readability.}} I have no idea who "our team" refers to and since this is an IP we can't even properly interact with them (although I will leave a message on their talk page). I don't believe there is a consensus that it is acceptable to use large language models in articles, far less to add such acknowledgements. Comments? Is there another venue where this needs to be discussed? Mike Turnbull (talk) 14:06, 16 March 2025 (UTC)

:... just one very obvious flaw in [https://en.wikipedia.org/w/index.php?title=VG_(nerve_agent)&oldid=1280788122 the current version of the article] is the discrepancy between the rat oral toxicity figure of 3300 mg/kg in the "Toxicology data" section and the 5.4 mg/kg value in the chembox. My inclination is to revert back to the [https://en.wikipedia.org/w/index.php?title=VG_(nerve_agent)&oldid=1273946963 version of 4 Feb 2025] and try again. Mike Turnbull (talk) 14:44, 16 March 2025 (UTC)

::I think there's something similar going on in Draft:Norlichexanthone, which is the result of a university group project (see discussion on my talk page for more). Esculenta (talk) 15:39, 16 March 2025 (UTC)

:::Support. Revert VG (nerve agent) and ask for stepwise edits, followed by appraisal by experienced editors. Thank you for identifying this issue. --Smokefoot (talk) 15:48, 16 March 2025 (UTC)

:::I declined Draft:Norlichexanthone. DMacks (talk) 02:21, 19 March 2025 (UTC)

:Support. Also suggest reversion to February 4th. Bizarrely searching google for one of the IP addresses used (213.124.171.69) now brings up the VG page as the top result. Anonrfjwhuikdzz (talk) 16:19, 16 March 2025 (UTC)

::After further investigation, I have reverted all these edits. I will now work to improve the article but that will take time as it needs a complete rewrite. Mike Turnbull (talk) 12:09, 18 March 2025 (UTC)

:I just identified an upload from User:Bram Lentjes on commons as attribution and license failure (claimed own, but is dup of another CC file). So either they are using AI for more than just grammar and tweaks of their own content (and in the process cut'n'pasting AI's failure to cite its own directly copied content) or their original writing itself has a shadow of potential plagiarism over it. DMacks (talk) 04:41, 19 March 2025 (UTC)

::Hi DMacks, could you elaborate on which picture this is? I hope I can shine some light on what went wrong and help fix it. Newtonpersquaremeter (talk) 15:00, 23 March 2025 (UTC)

:Hi Mike, I saw your comment and decided to make an account to contact you. As user Esculenta suggested, the edit on the amiton page was also the result of a group project for our course toxicology. I'm sorry to hear that our edits are not according to Wikepedia's standards and I would like to help improving our work to make it publishable again. About the aknowledgement: Including a statement about the use of AI in our project would result in bonus points for the project. And as the aknowledgement states, I (and as far as I know the rest of my group) only used AI to paraphrase. All the research done and sources found were done manually, without the use of AI. Could you please elaborate on the use of predatory journal as source (and other problems)? Newtonpersquaremeter (talk) 14:59, 23 March 2025 (UTC)

::Here are some comments from a regular editor here: most or at least a lot of homework assignments are substandard. Homeworkers are often undergrads who barely comprehend chemistry. Their work is generally unsupervised or lightly supervised by teachers who have no experience contributing content to Wikipedia. Wikipedia is not a platform for students/teachers who want to feel good about classroom projects. Good sources? Reviews in highly ranked scholarly journals, chapters from iconic textbooks. See WP:SECONDARY, WP:TERTIARY.--Smokefoot (talk) 15:18, 23 March 2025 (UTC)

:::To be fair, I am unqualified in chemistry and have written some fairly decent articles (I don't know nothing, but that's about it). A lot of it is just understanding how to write for Wikipedia, which the education program helps with Mrfoogles (talk) 04:05, 27 March 2025 (UTC)

::@Newtonpersquaremeter there was so much wrong with the version of the article which I linked above that I hesitate to point out all the problems. To take only the most obvious: 1) The toxicology section. Pubchem is not really a source: it is a database that collects together information published elsewhere. The editor who added the figure of 3,300 mg/kg for the LD₅₀ had in any case misread pubchem, which has the value as 3,300 ug/kg (i.e. a factor of 1,000 more toxic) and should have quoted the original source which pubchem provides. Extrapolating this to humans is fraught with problems and should never be done here in Wikipedia without a cast-iron source: none was provided. I used the secondary source from the ICI book, which states the rat LD₅₀ as "about 5 mg/kg", which is close enough: the point is that this value is similar to that for parathion, a widely use material at that time. Amiton was, as far as I am aware, never marketed and over-emphasis on its toxicity is irrelevant to its notability as the first V-agent.

::2) A more egregious error was to use doi:10.13188%2F2328-1723.1000019 as a "source" for the Adverse Effects and Toxicity section. That is a predatory journal and, more to the point, neither it or the other cited source for that section even mentions amiton: which is not surprising since as I've stated, it was never marketed!

::3) Now to the use of doi:10.1080/10426507.2018.1540491 as a "source" for the chemical synthesis section. You editor can't have read that paper, since it doesn't mention how amiton is made: it is a brief account of how it can be assayed for acetylcholinesterase activity. I suspect that this editor made up the information from general knowledge of organic chemistry and then added that citation as a plausible place which might have had the information. Sadly, it doesn't. There are proper ICI sources for the synthesis, which I have now included.

::It is completely unacceptable to me that any set of editors should use Wikipedia as an outlet for coursework without rigorous oversight from experienced supervisors in order to guard against the sorts of errors I have mentioned. Anyone who thinks that LLM are appropriate at their present state of development for writing Wikipedia articles is, in my opinion, seriously misinformed. Mike Turnbull (talk) 15:55, 23 March 2025 (UTC)

:::@Michael D. Turnbull I took some time to dig into these problems.

:::1) the problem with the 3,300 is caused by a mistake of a group member. In the Netherlands (where we live), the , is used as a decimal separator instead of the . Therefore this mistake was made out of habit, and the wrong notation was used. I do agree with you that they should've used the source cited by pubchem. About the extrapolation to humans: I have not done this research, so I cannot comment on what they exactly did there.

:::2) We (or at least I) didn't know this was a predatory journal. I didn't write this section either so again i cant comment on why this happened.

:::3) This is a mistake on my side; I did the reference list, and to make the refences I used the automatic citation tool. The tool grabbed a different paper from the same author, and I did not check if it was correct, the authors matched. As seen in the edit [https://en.wikipedia.org/w/index.php?title=VG_(nerve_agent)&oldid=1280610602 14:34, 15 March 2025], the actual source is Althoff MA (2018). Karaghiosoff KL; Klapötke TM (eds.). Preparation and analytical investigation of Amiton and Amiton-like compounds closely related to the Chemical Weapons Convention, instead of Althoff, M. A.; Unger, C. C.; Bützer, P.; Metzulat, M.; Klapötke, T. M.; Karaghiosoff, K. L. (2019-02-07). "Bioactivity and toxicological study of Amiton and related isomers". This source does contain the information about the synthesis of Amiton. This fault is on me and next time I will make sure all sources are checked.

:::I do agree with you that for this project to be benificial for Wikipedia, more supervision is needed. Also, I agree that LLM's are not appropriate to write Wikipedia pages. I believe this isn't the professors stance either; I think the idea behind the bonus point for AI aknowledgement is that they know they cant make sure we don't use it, so it is better to actually properly reference to the AI used. Newtonpersquaremeter (talk) 20:56, 23 March 2025 (UTC)

::::@Newtonpersquaremeter: a couple of points based on your reply. The source you mentioned above for the synthesis is [https://edoc.ub.uni-muenchen.de/22609/1/Althoff_Marc_Andre.pdf this thesis] by Althoff. We tend to avoid theses as direct sources since they are not peer-reviewed and can be error-prone. They can be good sources if one takes the trouble to drill down into them and seek out the underlying literature. Althoff does cite doi:10.1039/JR9600000637, which is what I have now used for the synthesis section. We have guidance on using LLM: see the essay WP:LLM and its talk page. There is no consensus for their use but they are not forbidden by policy. I personally would never use them but the main point is that anyone who does is supposed to say so in their edit summary, not in the actual article. Thanks for being prepared to discuss these issues: Wikipedia can only be successful if editors communicate. Mike Turnbull (talk) 11:42, 24 March 2025 (UTC)

:::::@Michael D. Turnbull Thank you for your reply. I'll keep these things in mind for the future. And no problem, I'm glad I could help! Newtonpersquaremeter (talk) 19:03, 24 March 2025 (UTC)

File:Information.svg There is a requested move discussion at Talk:Ergoamides#Requested move 23 March 2025 that may be of interest to members of this WikiProject. TarnishedPath^talk 03:22, 7 April 2025 (UTC)

I have nominated for deletion an article, arabilin, that may be of interest to members of this Wikiproject. See Wikipedia:Articles for deletion/Arabilin. Innerstream (talk) 12:58, 16 April 2025 (UTC)

At Tellurophenes, an article with an unusually large amount of detailed content, there is a requested move Tellurophenes → Tellurophene which could use the input of knowledgeable editors. Please comment at Talk:Tellurophenes#Requested move 4 May 2025 if interested. Adumbrativus (talk) 04:56, 14 May 2025 (UTC)

Fluspidine popped up as a new article, listed as PubChem [https://pubchem.ncbi.nlm.nih.gov/compound/71719166 CID 71719166]. PubChem calls that entry "[18F]-Fluspidine", which matches what our article's chemical is (both content and the cited ref). But that database's other mechanically derived entries (IUPAC name, SMILES, etc.) are instead specifically the ¹⁷F isotopolog. ChemBL [https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL2314421 CHEMBL2314421] likewise has contradictory isotopic details within this entry. Should we include these database tokens in the infobox and flag them somehow, or omit them and include a note explaining why? DMacks (talk) 14:09, 14 May 2025 (UTC)

:I'd leave the IDs out until the databases catch up, as they are likely to do. Meanwhile User:Boghog might like to update the .svg image file to show the correct isotope! We can, of course, alter the IUPAC name and SMILES we use as these are "sky-is-blue"-type information that doesn't need a specific citation. Mike Turnbull (talk) 17:01, 14 May 2025 (UTC)

:: :File:Fluspidine.svg {{fixed}}. Good catch DMacks. Boghog (talk) 18:23, 14 May 2025 (UTC)

:::That was me! I've reported the error to Chemspider for their #29397143, so hopefully that will get fixed. Mike Turnbull (talk) 10:18, 15 May 2025 (UTC)

:If there is a correct entry eg [https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL1645202 CHEMBL1645202] then please use that instead of a wrong or narrow one. But in this case I would put in a wikitext comment to state the wrong pubchem entry and what the problem is. That should stop someone else putting in the incorrect entry. Another common type of error in PubChem is a charge error, particularly for transuranic compounds. Graeme Bartlett (talk) 23:11, 14 May 2025 (UTC)

::The CHEMBL1645202 link goes to a page for the parent compound, presumably the 19F (i.e. normal) version. That page has a box lower right which links to CHEMBL2314421, describing it as the 18F compound but with the wrong drawing! Mike Turnbull (talk) 10:26, 15 May 2025 (UTC)

I see missing the articles about some important higher alkanes as hexacosane and dotriacontane, only their redirects exist. Can you create them? Thank you. 176.200.99.221 (talk) 13:42, 5 June 2025 (UTC)

:See Higher alkane.--Smokefoot (talk) 15:47, 5 June 2025 (UTC)

::I think are useful specific articles with chembox templates about hexacosane and dotriacontane like other higher alkanes (tetracosane for example) 109.54.249.228 (talk) 06:12, 9 June 2025 (UTC)

::P.S. Exist also articles about alkanes with more carbon atoms (nonacosane and hentriacontane) 109.54.249.228 (talk) 06:36, 9 June 2025 (UTC)

:::IP editor. So do them yourself if you wish. The existing articles that you mention barely demonstrate the notability of the ones we do have. Mike Turnbull (talk) 11:51, 9 June 2025 (UTC)

Cocaine this article needs some attention from an expert in the field it has been overwhelmed with copy pasting. Moxy🍁 00:08, 10 June 2025 (UTC)

Do I just add something like "also abbreviated as GA" in the article so I can finally include it in the GA (disambiguation) page? I had a talk with Bkonrad; more details over there. CheckNineEight (talk) 12:54, 11 June 2025 (UTC)

Over at Talk:Ecarin, {{ping|Altoids0}} proposed a merge of the articles Ecarin and Scutelarin. To quote them, this was their reasoning:

{{Quote|"I am not an expert in this field or anything but it seems to me that, per the BRENDA entry, Ecarin is a synonym or alternative name for Scutelarin. Is this grounds for merging, or is it acceptable that the two enzymes share the same number?"}}

Should the merge happen? I'd like your inputs. 1isall (talk/contribs) 20:42, 21 June 2025 (UTC)

:To elaborate, by "number" I mean that they seem to share the same Enzyme Commission number. The article on the topic seems to indicate that enzymes sharing a number is possible, but that plus the "alternative name" thing (and the fact that this article has an LLM maintenance tag) left me still skeptical. Altoids0 (talk) 20:43, 21 June 2025 (UTC)

::Thanks for the elaboration! 1isall (talk/contribs) 21:09, 21 June 2025 (UTC)

Aspirin 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) 02:01, 25 June 2025 (UTC)

The article prose identifies itself as the set of isomers ever since its creation, consistent with its infobox and the associated wikidata item :d:Q55974003. Most, but not all of the other languages linked from that wikidata item are likewise the set of isomers. However, one language is instead just the 1-chloro isomer. And our article's prose discussing use (and the only mentioned aspect of notability) is only the 2-isomer (stereochemically agnostic), which is consistent with what I find from a quick lit search as being the one worth an article. So...

Should our article have its isomer-specific content split off to a new article, and potentially nuking (or stripping down, or redirecting to the chemical-formula set-index) the isomeric-mix page? Or should our article be tweaked to be only about the notable isomer? Either way, we need some multi-wiki wikidata cleanup and new items also, but I as usual don't know how wikidata items get created. DMacks (talk) 23:19, 29 June 2025 (UTC)

:My opinion is that the article should be on the one useful isomer. It can mention the other isomer, but should be primarily about the single useful one. Wikidata should have separate entries for a group of isomers with the same name, group of stereoisomers and an individual stereoisomer. So it should link to another Wikidata entry other than the group. The other isomers are probably not notable, and so do not deserve separate articles or a set index! If a Wikidata item is missing we can create it. But many are pre-existing based on I don't know who's work. Graeme Bartlett (talk) 04:40, 30 June 2025 (UTC)

:It's possible that's just produced this way. The reaction of phosgene and ethylene oxide, or the chlorination of ethyl formate might both give a mixture of isomers? Project Osprey (talk) 09:52, 30 June 2025 (UTC)

::Both compounds (one as a racemate) are available from Aldrich but neither has a REACH listing as they aren't produced on a large enough scale. I'll do some tweaking now based on the Aldrich data sheets and any other decent references I can find, which hopefully will deal with the notability issue. In principle there's no reason why all isomers can't be described in one article but let's see how the search for more information goes. Wikidata is beyond my competence. Mike Turnbull (talk) 11:20, 30 June 2025 (UTC)

:::Whatever the heck kind of magic happens over there, I finally found :d:Q5103063 and :d:Q27259425 and shifted Claudio Pistilli's eowiki nonsense to the correct one. DMacks (talk) 13:33, 30 June 2025 (UTC)

::According to SciFinder, there are distinct methods that give one vs the other constitutional isomer. For example, the phosgene (or synthon of it) + ethylene oxide (or synthon of it) are a set of known reactions for producing 2-chloro but not 1-chloro, and I can't think of a likely mechanism that would give that alternate product. Conversely, phosgene (or synthon of it) + acetaldehyde gives only 1-chloro. A review article that discusses some advances in the phoshene route to 1-chloro, and calls that isomer "industrially important".{{cite journal |doi =10.1081/SCC-120021030 |year =2003 |volume =33 |issue =12 |last1 =Flosser |first1 =David A. |last2 =Olofson |first2 =Roy A. |title =Improved Synthesis of Dialkylaminopyrrolines |journal =Synthetic Communications }} but 2-chloro does have lots of "reactant" uses in journal articles. Free-radical chlorination does give a mixture, but is only listed in a patent (not WP:RS itself). So I don't see "mixture of 1- and 2- isomers" as a basis for an article (not a notable thing itself) or necessary WP:PARTIALDAB (we already have C3H4Cl2O2 as a DAB). DMacks (talk) 11:29, 30 June 2025 (UTC)

:::I would support splitting in that case. EROS has separate articles for them: 1-Chloroethyl {{DOI|10.1002/047084289X.rc102}}, 2-Chloroethyl {{DOI|10.1002/047084289X.rn01309}}. Project Osprey (talk) 12:22, 30 June 2025 (UTC)

:::In that case splitting sounds good, as long as there is some content! Graeme Bartlett (talk) 12:44, 30 June 2025 (UTC)

::::I've added some content. The syntheses are interesting if only for their simplicity from common starting materials. I wouldn't object to a splitting, if anyone wants to do that. Mike Turnbull (talk) 15:55, 30 June 2025 (UTC)

:For the isomers, wikidata: d:Q5103063 is for 1-chloroethyl chloroformate and d:Q27259425 for 2-chloroethyl chloroformate which has 2 articles linked.

:I did the split. Thanks everyone for working on these! DMacks (talk) 05:53, 1 July 2025 (UTC)

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