Wikipedia talk:WikiProject Chemistry/Archive 55

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Archive 55

Sciencemadness.org

An insource search shows that we currently have 70 cases where Sciencemadness.org has been used in chemistry articles. Some uses (e.g. in Copper(I) phosphide, current citation #6) have that wiki as a source for our Wikipedia article, although Sciencemadness itself usually does not cite any sources and is clearly not reliable by our standards. More worryingly, it seems that many of the instances of links to that website are to books and articles which are copyright. For example, Tetrafluorohydrazine has a citation #3 to John Drury Clark's 1972 book "Ignition" with a link to a scanned copy as a .pdf. I think we need to go through all 70 instances and either remove the cite or, if the cite itself is valid, remove the links to the copyvio. Comments? Mike Turnbull (talk) 14:29, 28 May 2024 (UTC)

Support Pygos (talk) 15:07, 28 May 2024 (UTC)

I've changed the Tetrafluorohydrazine citation to point to the Google Books preview rather than Sciencemadness.org. I can probably do the same with a lot of these links. Reconrabbit 15:22, 28 May 2024 (UTC)

Thanks, User:Reconrabbit. I was intending to do similar but was waiting a bit to see if anyone had reasons not to do that. Mike Turnbull (talk) 15:27, 28 May 2024 (UTC)

Support replacing those links. A number of dubious sources are cited in our articles, so it is a good idea to root them out. Educational sites include Khan Academy (https://www.khanacademy.org/science/organic-chemistry) and ChemLibre (https://chem.libretexts.org/Bookshelves/Organic_Chemistry) seem to present legitimate information, but they probably are not reliable sources. The overarching problem is that most good content sits behind paywalls.--Smokefoot (talk) 15:48, 28 May 2024 (UTC)

That's a good point. Editors here who write chemistry articles should have access to paywalled sources either through their institution or the Wikipedia Library, for example. Provided we summarise such sources accurately, it doesn't matter that the average reader can't themselves easily read the sources. We must try to write quality articles and that often means citing specialist publications. Mike Turnbull (talk) 17:36, 28 May 2024 (UTC)

Chemistry LibreTexts is a tricky one out of these; the attribution is terrible, but I have included them as references on some topics because I have had trouble finding online sources that define in basic terms specific concepts like crystal field excitation. Reconrabbit 16:02, 28 May 2024 (UTC)

In the spirit of gaining some consensus on on-line sources, another one is American Elements (https://www.americanelements.com). Dozens or hundreds of chem articles cite this website. Maybe someone can comment on their status as an RS. Like Sigma-Aldrich or other vendors, their physical data are probably acceptable. But they dress up their articles with a narrative, which is not verifiable and is not reviewed in any way. Their narratives are window dressing for the products that they are selling.--Smokefoot (talk) 22:49, 28 May 2024 (UTC)

I support not using American Elements for "use" verification, as we cannot see where their info came from, and when trying to confirm, perhaps only one researcher tried that application. Graeme Bartlett (talk) 00:01, 29 May 2024 (UTC)

Contents from American Elements may contain original research. --Leiem (talk) 15:08, 29 May 2024 (UTC)

Sciencenotes.org is another site that shows up infrequently and is written largely by two people with scientific backgrounds but no oversight. Reconrabbit 23:43, 28 May 2024 (UTC)

I have now replaced or removed all but one reference to Sciencemadness.org. Graeme Bartlett (talk) 01:36, 29 May 2024 (UTC)

Thanks for doing that heavy-lifing! DMacks (talk) 02:24, 29 May 2024 (UTC)

@Graeme Bartlett:Thanks for removing the direct Sciencemadness.org cites. The insource search at the top of this thread is still giving 62 hits which are copyvios IMO. I'll start trying to replace them, and User talk:Reconrabbit will probably assist. Mike Turnbull (talk) 10:17, 29 May 2024 (UTC)

Use in Nicotine and pyridine is not a copyvio, as works are in public domain. Graeme Bartlett (talk) 12:46, 29 May 2024 (UTC)

OK, I'll check as I go. Mike Turnbull (talk) 13:36, 29 May 2024 (UTC)

There are also several US government publications which are in the public domain. Though I am not sure about LANL publications: are they government or not? Graeme Bartlett (talk) 04:48, 1 June 2024 (UTC)

I think the LANL ones are OK. Part of the website says that's where those documents originally came from. Their library has many books that are clearly PD owing to age but also quite a few I would consider to be copvio as too recent. Anyway, those linked from cites in our articles has been trimmed down to the extent where I'm giving up on the final ones. Mike Turnbull (talk) 11:04, 1 June 2024 (UTC)

Sources

Ok, maybe we transition to a related topic. If one does not have access to basic textbooks, it is next to impossible to edit technical content. "Crystal field excitation" is not a term encountered very often. Yes, one can imagine what it is, but the phrase is not indexed in usual textbooks (Wiberg, Cotton&Wilk, Shriver). My somewhat obnoxious point is that if one is struggling to find a source for a topic, maybe that topic does not merit an article. --Smokefoot (talk) 17:23, 28 May 2024 (UTC)

Ninovium

I just found ninovium article. I think this article should either be merged with Victor Ninov or with oganesson. Could somebody please take a look? ReyHahn (talk) 13:26, 15 May 2024 (UTC)

It is probably better merged with Ninov's article, since the fraud has become a pretty defining event of his career; for oganesson, it would be a history subsection at most.

Certainly doubt it merits its own page, especially under the current name - and especially one that introduces it as "a synthetic element", and says things like "ninovium's existence as a valid element remains unsubstantiated, and its characteristics remain uncertain" - which makes me wonder if the page's author understands that the claimed "ninovium" necessarily is oganesson. The whole incident could warrant something like element 118 falsification scandal, I suppose?

I would say redirect "ninovium" to oganesson#Unconfirmed discovery claims, while integrating the salvageable parts of the existing article into Ninov's? Fishsicles (talk) 18:28, 7 June 2024 (UTC)

More organophosphate questions

Sorry for the continuing questions in this area. Are there any reactions of organophosphates that can change the PO₄ core (i.e. other than hydrolysis or transesterification)? I can't find any, beyond perhaps carbothermal reduction to elemental P. I find that surprising - it would make it the only functional group I can think of that cannot be converted into different functional group. Project Osprey (talk) 21:35, 9 June 2024 (UTC)

phospha-Fries rearrangement might be of interest? Fishsicles (talk) 22:34, 9 June 2024 (UTC)

Interesting, and new to me. Thanks --Project Osprey (talk) 23:17, 9 June 2024 (UTC)

Well, phosphate, sulfate, and orthosilicate are indeed pretty dead. A look at the "bible" (Greenwood and Earnshaw) does not help much. In synthetic chemistry, it seems that the negative charge needs to be dealt with before anything happens. Maybe protonation sets the scene for condensation leading ultimately to P4O10 or things like that, which then can be sulfided (by P4S10) and chlorinated. The other way to address the issue is, of course, is biochemistry: organisms have been stuck with these oxyanions for billions of years. A quick glance shows the pyruvate enol phosphates, i.e., a phosphate ester, can be reduced to phosphinic acid level. doi 10.1146/annurev.biochem.78.091707.100215. You never get PH3 or element but organophosphorus compounds. On the silicate front, industry has long wishes to avoid SiO2 down to Si then back up to SiMe4-xClx, but I digress.--Smokefoot (talk) 23:21, 9 June 2024 (UTC)

Phosphoenolpyruvate mutase might be something to explore as well. Hopefully there are some nice mechanistic studies on the enzyme reaction. ― Synpath 05:15, 10 June 2024 (UTC)

Categories for Fiveling

There is a dispute between me and the article creator about how broad the categories for this article should be. See Talk:Fiveling#Intractable dispute over categories. –LaundryPizza03 (dc̄) 22:50, 10 June 2024 (UTC)

Pro-forma, please note that @LaundryPizza03 did notify me that he is cross-posting. Ldm1954 (talk) 02:05, 11 June 2024 (UTC)

Removing some Hindawi refs?

Apparently Hindawi (publisher) is a huge operation, occasionally putting out some controversial journals. Here are some that appear to apply to the Chemistry project:

• Advances in Materials Science and Engineering
• Biomed Research International
• Contrast Media & Molecular Imaging
• Disease Markers
• Evidence-Based Complementary and Alternative Medicine
• Journal of Environmental and Public Health
• Journal of Healthcare Engineering
• Journal of Nanomaterials
• Oxidative Medicine and Cellular Longevity

According to Retraction Watch the above journals (and others) have been "delisted" from Web of Science. So, I started to remove some of these references from chemistry articles. Are my removals a good idea?--Smokefoot (talk) 04:19, 13 June 2024 (UTC)

I think it would be a mistake to just remove the citations. Just because some indexer thinks a journal is lower quality, does not mean that an article in it is low quality. We'll probably need to replace by another reference if we take them out. I see usage in some broad topics that would easily be replaceable for important facts. Otherwise if the referenced text is garbage based on a garbage publication, then it should be removed altogether. So we should examine each use. {However I have deleted a chemical referenced to Journal of Nanomaterials from an article I wrote (as substance not well proved to exist) }. Graeme Bartlett (talk) 07:32, 13 June 2024 (UTC)

OK, I undid my edits. --Smokefoot (talk) 16:51, 13 June 2024 (UTC)

Helium Featured Article review

This discussion may be of interest to the community here. XOR'easter (talk) 20:35, 17 June 2024 (UTC)

RfC on meaning of nonmetal

There is a RfC on this topic at Talk:Nonmetal#RfC_on_meaning_of_nonmetal which may be of interest. Is the primary use of the term nonmetal for elements in the periodic table, see discussions in Talk:Nonmetal and also at Talk:Nonmetallic compounds and elements. Editor Sandbh is arguing that this is the case, with some other additions. Editors Johnjbarton, Ldm1954 and YBG have questioned this, and both Johnjbarton and Ldm1954 have questioned the scientific accuracy.Ldm1954 (talk) 07:46, 18 June 2024 (UTC)

Op-Ed: Runnin' blind

It is nearly impossible to write an overview of a topic without good sources. It can also be a disservice because the topic might be misrepresented. If one does not have access to the major works in an area, ask for help, pray that Google books gives you a glimpse to the good stuff, or forget the writing project because you will be forced to rely on old-timey literature and junky online stuff. Almost all the good on-line content is behind a paywall or is inside of major textbooks and encyclopedias. Some major works are online as pdf's, possibly illegally. March's Organic Chem is one example, Greenwood and Earnshaw for Inorganic (especially Main Group) is another. The major review journals (Chem Soc Rev, Angew, Chem Rev) have some open-access content. Org Syn is open access, but it does not provide sufficient context for an overview. --Smokefoot (talk) 13:32, 23 June 2024 (UTC)

McMurry's Organic Chemistry is now free-access online. DMacks (talk) 14:46, 23 June 2024 (UTC)

Yes, at Openstax, (at 193 Mb) which also has several other useful textbooks. Mike Turnbull (talk) 14:51, 23 June 2024 (UTC)

.... See also John E. McMurry and the McMurry reaction. Mike Turnbull (talk) 15:05, 23 June 2024 (UTC)

All true. One recent welcome trend is for authors of "the good stuff" to make it open access. A recent example is Peter Atkins making the latest version of Concepts in Physical Chemistry freely available and even downloadable at doi:10.1039/9781837674244. I've added that link to our article about him and would encourage anyone to use this to update relevant topics. In a related move, IUPAC have licensed their Gold Book CC BY-SA 4.0 which has allowed User:Walkerma to include their definitions unchanged into articles such as adsorption and Boltzmann constant. Fortunately, many good review articles are available via University subscriptions to journals, which is how some of our student editors will gain access. Others can reach JSTOR via the Wikipedia library. My pet peeve is that the American Chemical Society don't seem to provide better access via that or other similar mechanism. Mike Turnbull (talk) 14:46, 23 June 2024 (UTC)

Maybe we should assemble a list with links on our project page?--Smokefoot (talk) 15:01, 23 June 2024 (UTC)

Good idea, which I see you have begun to do. We just need to ensure that no-one adds a WP:ELNEVER to a copyvio version of something. Mike Turnbull (talk) 15:56, 23 June 2024 (UTC)

It would be great if Chemical & Engineering News was easier to access beyond the first "free article"; their online archives are extensive. Could be a proposal for WP:TWL? Reconrabbit 16:40, 23 June 2024 (UTC)

Its an ACS magazine, hence that problem. However, if you know the URL (from their website) that you want, you can often find it archived at the Wayback Machine etc. So, for example, this one . How this squares with WP:ELNEVER I leave to the lawyers: safest would be to use the information you find to write your Wikipedia entry and cite it but not link it. Mike Turnbull (talk) 17:01, 23 June 2024 (UTC)

I don't imagine it would be different from any other situation where we link to paywalled articles. I did some digging and found a discussion on the External Links noticeboard that is tangentially related: Wikipedia:External_links/Noticeboard/Archive_25#Potential license laundering through ghostarchive.org Reconrabbit 17:52, 23 June 2024 (UTC)

I am guilty of sometimes citing refs that I cannot access. The usual scenario is that I'm reading paper 'A' and it states a fact with a reference back to paper 'B', but I cannot access paper 'B', If I can't find another option then sometimes I just accept the fact stated by 'A' and cite 'B' as the source. I've never been certain about this type of by-proxy sourcing. Similarly, I've cited Chem Rev articles when I cannot access them, but only when they are unambiguously relevant (name reactions, for instance). I have no access to pay-walled content beyond the Wikipedia Library, nor any SciFinder etc. I feel that I have become very good at finding sources by other means, but it can still be a challenge to write a new overview. Mostly it's just very slow, I've working on organophosphate for months and I'm still not done with it. What I will say is that I think it's better then when started. There are lots of pages like that, where if not good, they can at least be made not bad. --Project Osprey (talk) 20:32, 23 June 2024 (UTC)

A plea for help with the short list of good (and legal) open source reference works (which I put on our project page). Should we put this list in our Manual of Style (would it be ignored there?), should we leave it on the project page, should we do something else with this list? --Smokefoot (talk) 22:50, 23 June 2024 (UTC)

Our project page is a good place for it. The list is a bit out of scope for a manual of style. Reacting to Project Osprey's A references B, you must be very careful. You could just reference A. But in a significant number of cases I have found that the A paper misrepresents B, so it is best to make sure what it says before using it as a reference. Also thanks to Smokefoot for recommending Shriver & Atkin's Inorganic Chemistry 5th ed, which can also be found to read on archive.org. It is 14 years old. If this is entirely legal, then it would be worth a link too. Graeme Bartlett (talk) 10:35, 24 June 2024 (UTC)

Good article reassessment for Nature

Nature 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) 20:11, 26 June 2024 (UTC)

Arsenic trioxide dimer?

In Wikipedia:Featured article candidates/1858 Bradford sweets poisoning/archive1, I objected to the image File:As4O6-molecule-from-arsenolite-xtal-3D-balls.png being labeled as "arsenic trioxide" and suggested it might be a dimer. But I'm not sure if that's actually the correct term for this kind of structure. Could somebody with better chemistry-fu than me take a look? RoySmith (talk) 01:07, 16 July 2024 (UTC)

According to Arsenic trioxide it seems like it forms dimers at temperatures below 800 degrees Celsius, so for these circumstances it is accurate (assuming that the Wikipedia article is correct, of course). There are also polymeric allomorphs. Jo-Jo Eumerus (talk) 06:56, 16 July 2024 (UTC)

Under standard conditions it would appear to exist in the claudetite forms, so maybe switch one of those? --Project Osprey (talk) 08:59, 16 July 2024 (UTC)

Names of chemical formula with anions

Are there any names of chemical formulas with anions in the examples of Pentagonal pyramidal molecular geometry? I'm not expert at chemistry, but I probably need explanation. For example, can I called IOF²⁻
₅ as "iodine pentafluoride with two anions"? Dedhert.Jr (talk) 13:37, 18 July 2024 (UTC)

IOF
₅ is not iodine pentafluoride because there is an additional oxygen atom - it's iodosyl pentafluoride. IOF²⁻
₅ can be referred to as iodosyl pentafluoride dianion. Marbletan (talk) 14:53, 18 July 2024 (UTC)

Many thanks. Dedhert.Jr (talk) 01:26, 19 July 2024 (UTC)

@Dedhert.Jr Note that the dianion you are interested in is not the same thing as iodosyl pentafluoride. To take a simpler example, we have sulfur trioxide SO₃ and the sulfite dianion SO²⁻
₃. As these articles explain, the shapes of these are quite different and the latter has two more electrons than the former: you can have a sample of sulfur trioxide as-is but the sulfite can only exist in combination with a counterion, as a salt. So, returning to IOF²⁻
₅, the article in which it was first characterised is doi:10.1021/ja980057+ and you'll see that this was as its tetramethylammonium salt. Naming the dianion is complicated according to IUPAC conventions, and I don't suggest you try! The relevant guidance would be the Red Book, which you can download, but if you are not an expert, I would recommend just sticking to the molecular formula. Mike Turnbull (talk) 10:08, 19 July 2024 (UTC)

@Michael D. Turnbull Many thanks as well. I'm thinking about the GAN Pentagonal pyramid in which I wrote the molecule with a pentagonal pyramid structure. The name of the chemical formula is technically needed if I want to avoid WP:TECHNICAL. Dedhert.Jr (talk) 13:20, 19 July 2024 (UTC)

@Dedhert.Jr I'm not sure that guideline is very useful here! I think that the anion might formally be called pentafluoro-oxo-iodate based on the related X-ray structure of the hexafluoro one. However, Pubchem call the hexa compound hexafluoro(oxido)-λ⁷-iodane, which means this one would be pentafluoro(oxido)-λ⁶-iodane and that's more in tune with the Red Book. You need an expert in inorganic nomenclature: maybe User:Double sharp could oblige. Incidentally, a better citation for the GAR than your current Baran one is his 2008 review at doi:10.1016/j.jfluchem.2008.06.016, which talks about all sorts of coordination geometries. I added that cite to the chemistry article today after replying here. Mike Turnbull (talk) 16:17, 19 July 2024 (UTC)

I have to agree with Michael D. Turnbull here: it's probably going to be easier to understand the formula than the name! I think he's given you the correct substitutive name indeed, but probably the additive name is more familiar: pentafluoridooxidoiodate(2−). Double sharp (talk) 03:30, 20 July 2024 (UTC)

@Double sharp, @Michael D. Turnbull Many thanks again. However, are there any chemical compound with pentagonal pyramidal structure other than IOF²⁻
₅? In GA square pyramid, it mentions the name of chemical compound with square pyramidal structure. Since both articles are mathematics topics, I cannot add the chemical compound rather than its name; or we can see another in Triaugmented triangular prism. Dedhert.Jr (talk) 04:40, 20 July 2024 (UTC)

@Dedhert.Jr: This Chemistry Stack Exchange comment contains links to papers describing such compounds. Double sharp (talk) 04:44, 20 July 2024 (UTC)

RfC: On discovery of the 23 nonmetals

Should this content on the discovery of the 23 nonmetals be removed from the nonmetal article?

RfC is here. --- Sandbh (talk) 13:39, 23 July 2024 (UTC)

Access to ACS journals via The Wikipedia Library

Currently, the TWL offers comprehensive access to literature ressources relevant to chemistry. The likely most important collection of scientific journals in the field of chemistry, which also partially covers neighboring disciplines including physics, biology, materials science or nutritional science, is published by the American Chemical Society (ACS). Unfortunately, TWL does not offer access to the ACS journals. In the Wikimedia Phabricator's TWL area the potential subscription to the ACS journal collection is currently listed under "Prospects". The number of Wikipedia authors supporting such a subscription is apparently relevant to the prioritization of new TWL subscriptions. Therefore, my request would be that anyone, who is also interested in getting access to the ACS journals, supports the proposal to subscribe to the ACS journals. For this purpose, log in to TWL, go the "suggest a collection" page (https://wikipedialibrary.wmflabs.org/suggest/), scroll down to the ACS entry and click on "Support". This doesn't cost much... Thanks for any support! Espresso robusta (talk) 13:42, 4 August 2024 (UTC)

@Espresso robusta Great suggestion! Unfortunately, the upvotes are currently only at 30, which still places us quite low in the list. Mike Turnbull (talk) 16:50, 4 August 2024 (UTC)

@Espresso robusta thanks for suggesting! I have an ACS membership so get some access that way but for scientists who don't have access via industry or university it would be a great resource. 34 upvotes isn't too bad for a niche area... Nnev66 (talk) 17:03, 5 August 2024 (UTC)

Potassium hexacyanidoferrate(III)‎... wha?

This tortured IUPAC nomenclature. Unfortunate. Practicing chemists do not use this term. --Smokefoot (talk) 16:51, 13 June 2024 (UTC)

Any time I've seen this out in the wild (I'm sure I have somewhere) it's been potassium ferricyanide which is where it was just moved from. If it really had to be at the IUPAC name, shouldn't it get moved to Tripotassium;iron(3+);hexacyanide? There's a reason the water page isn't called Oxidane.

Also possibly relevant, Potassium trichloridocuprate(II). Reconrabbit 20:20, 13 June 2024 (UTC)

Even Potassium hexacyanoferrate(III) was much more commonly used. I have moved the page back to potassium ferricyanide which is more commonly used by about a factor of 1000. Wikipedia policy is to use the most frequently used name rather than official (here closest to IUPAC). Letting @JWBE: know about reversion of the move. Graeme Bartlett (talk) 22:48, 13 June 2024 (UTC)

Greetings, Smokefoot! I have also found several instances of this, like with DIBAL and Red-Al. I am pretty sure that it would be fine to refer to DIBAL as, well, DIBAL. However, do you think it appropriate to refer to Red-Al as Red-Al due to it being a trade name? Pygos (talk) 13:19, 14 August 2024 (UTC)

The structure of tantalum pentoxide

File:Kristallstruktur_Triuranoctoxid.png

Tantalum pentoxide (Ta₂O₅) currently shows the crystal structure for Triuranium octoxide (U₃O₈). We frequently use use crystallographic archetypes in this way, but looking closer, I don't think this one is right. The stoichiometries don't add up, the uranium compound is mixed valance (V,VI) but the Tantalum one isn't. The imagine has been used this way on all the non-English pages as well. Project Osprey (talk) 15:38, 16 August 2024 (UTC)

Let me see what I can find. Usually Ben Mills does these images. --Smokefoot (talk) 16:03, 16 August 2024 (UTC)