Wikipedia talk:WikiProject Chemistry/Archive 55
 | This is an archive of past discussions on Wikipedia:WikiProject Chemistry. Do not edit the contents of this page. If you wish to start a new discussion or revive an old one, please do so on the current talk page. |
| Archive 50 | ← | Archive 53 | Archive 54 | Archive 55 | Archive 56 |
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)
- Support Pygos (talk)
- 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
- 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)
- 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)
- 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)
- 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)
- 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
- 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)
- 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)
- Contents from American Elements may contain original research. --Leiem (talk)
- 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)
- Sciencenotes.org is another site that shows up infrequently and is written largely by two people with scientific backgrounds but no oversight. Reconrabbit
- I have now replaced or removed all but one reference to Sciencemadness.org. Graeme Bartlett (talk)
- Thanks for doing that heavy-lifing! DMacks (talk)
- @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)
- Use in Nicotine and pyridine is not a copyvio, as works are in public domain. Graeme Bartlett (talk)
- OK, I'll check as I go. Mike Turnbull (talk)
- 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)
- 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)
- 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)
- 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)
- OK, I'll check as I go. Mike Turnbull (talk)
- Use in Nicotine and pyridine is not a copyvio, as works are in public domain. Graeme Bartlett (talk)
- @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)
- Thanks for doing that heavy-lifing! DMacks (talk)
- 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)
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)
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)
- 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)
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)
- phospha-Fries rearrangement might be of interest? Fishsicles (talk)
- Interesting, and new to me. Thanks --Project Osprey (talk)
- 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)
- 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)
- Interesting, and new to me. Thanks --Project Osprey (talk)
- Phosphoenolpyruvate mutase might be something to explore as well. Hopefully there are some nice mechanistic studies on the enzyme reaction. ― Synpath
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)
- Pro-forma, please note that @LaundryPizza03 did notify me that he is cross-posting. Ldm1954 (talk)
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)
- 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)
This discussion may be of interest to the community here. XOR'easter (talk)
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)
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)
- McMurry's Organic Chemistry is now free-access online. DMacks (talk)
- Yes, at Openstax, (at 193 Mb) which also has several other useful textbooks. Mike Turnbull (talk)
- .... See also John E. McMurry and the McMurry reaction. Mike Turnbull (talk)
- .... See also John E. McMurry and the McMurry reaction. Mike Turnbull (talk)
- Yes, at Openstax, (at 193 Mb) which also has several other useful textbooks. Mike Turnbull (talk)
- 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)
- Maybe we should assemble a list with links on our project page?--Smokefoot (talk)
- 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)
- 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)
- 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
- 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)
- 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
- 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
- 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)
- Maybe we should assemble a list with links on our project page?--Smokefoot (talk)
- 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)
- 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)
- 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)
- 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)
- 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)
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)
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)
- 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)
- Under standard conditions it would appear to exist in the claudetite forms, so maybe switch one of those? --Project Osprey (talk)
- Under standard conditions it would appear to exist in the claudetite forms, so maybe switch one of those? --Project Osprey (talk)
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)
- 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)- Many thanks. Dedhert.Jr (talk)
- @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)- @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)
- @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)
- 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)
- @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)- @Dedhert.Jr: This Chemistry Stack Exchange comment contains links to papers describing such compounds. Double sharp (talk)
- @Dedhert.Jr: This Chemistry Stack Exchange comment contains links to papers describing such compounds. Double sharp (talk)
- @Double sharp, @Michael D. Turnbull Many thanks again. However, are there any chemical compound with pentagonal pyramidal structure other than IOF2−
- 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)
- @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)
- @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)
- @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−
- Many thanks. Dedhert.Jr (talk)
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)
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)
- @Espresso robusta Great suggestion! Unfortunately, the upvotes are currently only at 30, which still places us quite low in the list. Mike Turnbull (talk)
- @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)
Potassium hexacyanidoferrate(III)... wha?
This tortured IUPAC nomenclature. Unfortunate. Practicing chemists do not use this term. --Smokefoot (talk)
- 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
- 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)
- 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)
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)
- Let me see what I can find. Usually Ben Mills does these images. --Smokefoot (talk)
Ethanol vs. methanol
Hello WikiProject Chemistry! Could I get someone's eyes on 2016 Irkutsk mass methanol poisoning to make sure I've characterized these two substances correctly? The article is currently at WP:FAC. (And would anyone be game to stage and take a comparison photo of the two to demonstrate how similar they appear...?) Ed [talk] [OMT]
- I have stock of both chemicals around, I can easily do a photo of each in side-by-side labeled vials later today. We've generally shied away from those on chemical articles (so I'm not surprised we don't already have each in c:Category:Methanol and c:Category:Ethanol), since they're both identical appearance clear colorless liquids. But obviously that comparison is relevant here. DMacks (talk)
- @Dmacks: Thank you so much! A photo was a great suggestion from a reviewer at the FAC and will help to communicate how these people unknowingly drank methanol. Ed [talk] [OMT]
- @DMacks: fixing ping. Ed [talk] [OMT]
- I actually think that showing ethanol and methanol side-by-side is a great idea because (not despite) them being
both identical appearance clear colorless liquids.
That would illustrate rather beautifully why the poisonings happen. Jo-Jo Eumerus (talk)- They also have similar odours, which is rather harder to show in an article here! Concluding that the similarity in appearance was the reason for the poisonings would be original research: those who drank the stuff knew they had purchased bootleg "bath oil" to avoid the tax on alcohol. Mike Turnbull (talk)
- Sorry for the delay, @The ed17 and Jo-Jo Eumerus:! Here you go: File:Methanol ethanol vials.jpg. Mike Turnbull makes a good point, that there should be a cited statement that they cannot be distinguished by appearance. This is mentioned without cite in methanol#Toxicity, and surprisingly not even mentioned at all in methanol toxicity. The statement in the FAC article is "Methanol is cheaper than ethanol, and the two cannot readily be distinguished." but the given NYTimes ref does not appear to mention anything related to that second clause. DMacks (talk)
- @Michael D. Turnbull and DMacks: Oof. So I dug into that and found the phrase was added just a day after the article was created, and I never noticed that the info didn't match up with the attached ref. Thank you for your diligence, and to Dmacks for the photo. I've added a Britannica reference to replace it -- I was surprised to find that it wasn't the easiest thing to find a replacement ref for. Ed [talk] [OMT]
- @Michael D. Turnbull and DMacks: Oof. So I dug into that and found the phrase was added just a day after the article was created, and I never noticed that the info didn't match up with the attached ref. Thank you for your diligence, and to Dmacks for the photo. I've added a Britannica reference to replace it -- I was surprised to find that it wasn't the easiest thing to find a replacement ref for. Ed [talk] [OMT]
- Sorry for the delay, @The ed17 and Jo-Jo Eumerus:! Here you go: File:Methanol ethanol vials.jpg. Mike Turnbull makes a good point, that there should be a cited statement that they cannot be distinguished by appearance. This is mentioned without cite in methanol#Toxicity, and surprisingly not even mentioned at all in methanol toxicity. The statement in the FAC article is "Methanol is cheaper than ethanol, and the two cannot readily be distinguished." but the given NYTimes ref does not appear to mention anything related to that second clause. DMacks (talk)
- They also have similar odours, which is rather harder to show in an article here! Concluding that the similarity in appearance was the reason for the poisonings would be original research: those who drank the stuff knew they had purchased bootleg "bath oil" to avoid the tax on alcohol. Mike Turnbull (talk)
- @Dmacks: Thank you so much! A photo was a great suggestion from a reviewer at the FAC and will help to communicate how these people unknowingly drank methanol. Ed [talk] [OMT]
Carbocation business
I am contemplating changes affecting at least 4 articles. The evolving plans are described at Talk:Carbocation#Merge proposal:
- relocate most, not all, carbenium ion (R3C+) content from carbocation to carbenium ion article.
- relocate most, not all, carbonium ion (R5C+) content from carbocation to the carbonium ion article with a sections on some individual nonclassical carbocations such as 2-norbonyl cation and many others.
- convert carbocation into a concise summary of these two kinds of cations, keep the "history" and the "nomenclature".
move 2-Norbornyl cation to Norbornyl cation debate to incorporate all that history. This debate, once a "thing", was settled when the X-ray structure was announced in 2013. It is doubtful that many readers want to wade through that history. 2-Norbornyl cation would redirect to carbonium ion#2-Norbornyl cation together with related cations such as homoallyl cation and cyclopropyl methyl cation.I am not an expert on these topics in case you are wondering.--Smokefoot (talk)
- I would appreciate the "debate" to be a separate article, as it gets difficult to read what the current beliefs about it are with that massive history and theory included. But I think 2-Norbornyl cation has enough material to be its own article. Graeme Bartlett (talk)
- I like it! For (3), don't forget to include vinyl cation, and a mention of the false teaching tool of drawing acylium ions with a carbonyl-carbocation resonance form (see doi:10.1021/ed5002152). DMacks (talk)
- Sounds good. There is a problem with the lead in carbenium ion "But IUPAC confuses...." which is only referenced to the IUPAC definition. This needs to be re-written carefully to avoid being WP:OR. Carbocation#Definitions may clear this up. Mike Turnbull (talk)
- I will follow the suggestions above. Also, this thing showed up: nonclassical ion, which could be a home for relatives of 2-Norbornyl cation-like species or could be redirected to carbocation. And then Pyramidal carbocation. Someone might inspect (remove???) the extensive calculations and theory, we dont do that kind of analysis typically.--Smokefoot (talk)
- If you think you can improve it then be bold. If you have reservations, then maybe do the new pages in a sandbox and we can see later? Some comments: (1) We normally use the simplest example of a functional group as an archetype for our descriptions, but methenium basically doesn't exist. It might be easier to use the t-butyl cation. Butylation is big business, so it is relevant and there may be better references. (2) The alkylation of alpha-olefins to give linear alkylbenzene illustrates the behaviour of secondary carbenium ions (i.e. they clearly exist, but the the charge moves freely up and down chain, giving a range of products). The Wagner–Meerwein rearrangement for the industrial production of vitamin E (not shown on our page) is a nice example of this willingness to rearrange being put to practical use. The presence of a 3c-2e bond in some protonated alkenes (ethanium) seems to be at odds with Markovnikov's rule as it implies the cations can be terminal-ish, I'm not sure what the reality is there (do we ever see any completely linear alkylbenzenes?) --Project Osprey (talk)
- If you think you can improve it then be bold. If you have reservations, then maybe do the new pages in a sandbox and we can see later? Some comments: (1) We normally use the simplest example of a functional group as an archetype for our descriptions, but methenium basically doesn't exist. It might be easier to use the t-butyl cation. Butylation is big business, so it is relevant and there may be better references. (2) The alkylation of alpha-olefins to give linear alkylbenzene illustrates the behaviour of secondary carbenium ions (i.e. they clearly exist, but the the charge moves freely up and down chain, giving a range of products). The Wagner–Meerwein rearrangement for the industrial production of vitamin E (not shown on our page) is a nice example of this willingness to rearrange being put to practical use. The presence of a 3c-2e bond in some protonated alkenes (ethanium) seems to be at odds with Markovnikov's rule as it implies the cations can be terminal-ish, I'm not sure what the reality is there (do we ever see any completely linear alkylbenzenes?) --Project Osprey (talk)
- I will follow the suggestions above. Also, this thing showed up: nonclassical ion, which could be a home for relatives of 2-Norbornyl cation-like species or could be redirected to carbocation. And then Pyramidal carbocation. Someone might inspect (remove???) the extensive calculations and theory, we dont do that kind of analysis typically.--Smokefoot (talk)
Guidelines on chemistry solubility?
I originally posted this at the help desk: Wikipedia:Help desk/Archives/2024 September 1 - Wikipedia but was recommended to post this here.
On the MoS for line equations it merely says "Do not include phase definitions unless they are absolutely essential". Normally, the states of matter as written as, for example, AgCl(s), but on the silver chloride page the precipitate is written as a down arrow for 2 equations and with a subscript for the remaining. Does Wikipedia have a preferred style?
Also, on some pages, like silver phosphate, as well as the main article for solubility product, the solubility product is written with units at the end of it, when it is usually treated as a dimensionless quantity. Is there a preferred style? SecretSpectre (talk)
- You have already found WP:Manual_of_Style/Chemistry#Line_equations, which is where any agreement on the preferred style is likely to have been recorded. You can suggest/discuss additions to the guidelines right here, if you like. IMO if you are making a proposal to fix on a preferred style, you also need some way to identify by a search where we would need to change existing articles in the "wrong" style. Mike Turnbull (talk)
- The first question (states) is actually two ideas. One idea is whether to use the parenthetical letter vs up/down-arrow in an equation based on the merits or context of that equation. My position is that both are acceptable, but the arrow emphasizes that there is a phase change (such as "becoming a solid" or "coming out of solution") vs just being a solid. The other idea is the general goal of Wikipedia:Consistency, such as using the same thing within any one article. But I think consistency should always be secondary to clear and correct meaning, so I'm having trouble thinking of a time that both would be equally appropriately meaningful and still worth including. DMacks (talk)
- The first question (states) is actually two ideas. One idea is whether to use the parenthetical letter vs up/down-arrow in an equation based on the merits or context of that equation. My position is that both are acceptable, but the arrow emphasizes that there is a phase change (such as "becoming a solid" or "coming out of solution") vs just being a solid. The other idea is the general goal of Wikipedia:Consistency, such as using the same thing within any one article. But I think consistency should always be secondary to clear and correct meaning, so I'm having trouble thinking of a time that both would be equally appropriately meaningful and still worth including. DMacks (talk)
I have started a Featured article review of Heavy metal (elements), please follow the link to the source. Based upon reading the sources too many did not validate; Johnjbarton also had some serious criticisms. Ldm1954 (talk)
- N.B., the main page is Wikipedia:Featured article review#Heavy metal (elements), the link above goes directly to a page just on this FAR. Ldm1954 (talk)
Errors in a Periodic Table on Wikimedia Commons
It was brought to my attention that File:Periodic Table Of Elements Black And White.svg on Commons has multiple errors. There has been a comment on the file's talk page about the wrong atomic numbers since 2020. Does anyone know how to either get the file fixed or deleted? See below for comments copied from the file's talk page.
- The elements Te, and Ir -> Hg all have the wrong atomic numbers assigned to them. Griceylipper (talk)
- I noticed Thallium has "TI" (capital T, Capital I) as its symbol, not Tl (capital T, lower case l) - look at Chlorine (Cl) or Aluminum (Al) to see what a lower case "l" looks like. Ruhrfisch (talk)
Thanks, - Ruhrfisch ><>°°
- @Ruhrfisch That file doesn't seem to be used in any article in any language version of Wikipedia (see its Commons page) and the uploader hasn't made any contributions there since 2016 when it was uploaded. You can nominate the file for deletion using the menu on the left of its file page on Commons. Mike Turnbull (talk)
- @Griceylipper Apologies, I see it was you who made the original post, not Ruhrfisch. Mike Turnbull (talk)
- @Griceylipper Apologies, I see it was you who made the original post, not Ruhrfisch. Mike Turnbull (talk)
- For now I have added the Disputed chem template to the page so that others are warned about the problem and are less likely to attempt to use it. File:Periodic Table Of Elements.svg by the same uploader had similar issues, but most of the errors have already been corrected (Te still has the wrong atomic number though, so I've marked that one as disputed too). Marbletan (talk)
- I suggest just nominating both for deletion, I think there are enough others. Ldm1954 (talk)
- Thanks everyone - I have nominated the Commons file for deletion, here: c:Commons:Deletion requests/File:Periodic Table Of Elements Black And White.svg. - Ruhrfisch ><>°°
- The link is c:Commons:Deletion_requests/File:Periodic_Table_Of_Elements_Black_And_White.svg Mike Turnbull (talk)
- The link is c:Commons:Deletion_requests/File:Periodic_Table_Of_Elements_Black_And_White.svg Mike Turnbull (talk)
- Thanks everyone - I have nominated the Commons file for deletion, here: c:Commons:Deletion requests/File:Periodic Table Of Elements Black And White.svg. - Ruhrfisch ><>°°
- I suggest just nominating both for deletion, I think there are enough others. Ldm1954 (talk)
Hi! The regulars are CFD are not chemistry experts, so we would really appreciate your input at Wikipedia:Categories for discussion/Log/2024 September 15#Category:Chemical looping technologies. No knowledge of CFD policies/procedures necessary – the participants have a question about whether Chemical looping combustion and Chemical looping reforming and gasification belong in Category:Chemical process engineering or Category:Chemical processes. Best, HouseBlaster (talk • he/they)
Made-up chemical names!
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:
- "Benzane" for Cyclohexa-1,3-diene
- "Phenane" and "Phenylene hydride" for Benzene
- "Acetoic acid" and "Oxoacetal" for Pyruvic acid
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)
- They would be in the category of WP:Original research. Did any get created as redirects? Graeme Bartlett (talk)
- 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)
- @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)
- 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)
- 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)
- 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)
Chemical formulas on Wikidata
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)
- {{ping| AdrianoRutz} What exactly is the proposal? These discussions seem to be dominated by editors who have little cred in chemical editing.--Smokefoot (talk)
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- 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)
- 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)
- 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)
Chembox for a mixture?
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)
- @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)
- 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)
- 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)
- 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)
- 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)
- 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)
- 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)
- 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)
- 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)
- 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)
- 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)
- 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)
- 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)
Organic Reactions-sourced articles
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)
- 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)
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)
Computational chemistry
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)
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)
- @Wostr and Nucleus hydro elemon: Why would any editor work on this topic?--Smokefoot (talk)
- 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)
- 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)
- 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)
- 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)
- 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)
- 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)
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)
- For the record, ScienceDirect topic pages are considered "generally unreliable" by WP consensus for several reasons (Wikipedia:Reliable sources/Perennial sources). DMacks (talk)
- @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)
- 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)
- 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)
- 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)
- 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)
- 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)
- @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)
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)
- 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)
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)
Attribution (alkynylation reactions)
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)
- 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) 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)
References
- ^ 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.
Is there a place in Wikipedia to describe the history of atomic weight determination?
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)
- 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)
What the Di hydro gen monoxide?! Bearian (talk)
- Better or worse than Cold water pitting of copper tube? DMacks (talk)
- 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)
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)
Stereochemistry and isomers status report
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:
- "rotamer: One of a set of conformers arising from restricted rotation about one single bond." https://doi.org/10.1351/goldbook.R05407
- "conformer: One of a set of stereoisomers, each of which is characterized by a conformation.. minimum" https://doi.org/10.1351/goldbook.C01262
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
- Molecular geometry (24000 bytes)
- Comment: a lot is not about geometry, Sorta ungainly (molecular structure redirects here)
- Diastereomer (9400)
- Mostly focused on sugars
- Ring flip (9200)
- Mostly about cyclohexane
- Cyclohexane conformation (33,000)
- pretty redundant with ring flip
- Gauche effect (7600)
- Staggered conformation (1800)
- Eclipsed conformation (8100)
- Cyclic compound (28000)
- Seems ungainly to me, proteins, all chelate complexes, heterocycles….
- Conformation (980)
- Sorta a disambiguation site
--Smokefoot (talk)
Protein 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)
ZrSiS infobox?
Would it be possible to add an infobox to the Zirconium silicon sulfide article, or is there currently insufficient data to even make a start on this? — The Anome (talk)
- @The Anome: I added a box, but it appears not to be included in PubChem or ChemSpider (yet). Are there any related substances? Graeme Bartlett (talk)
High-level radioactive waste management 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)
AI is coming fast
So, I am constructing simple article on 4-nitroanisidine, which has many names depending on which functional group gets priority and whether one uses number, or ortho,meta, para. Then I Googled 2-methoxyl-4-nitroaniline and got this: "AI Overview: 2-Methoxy-4-nitroaniline (MNA) is an aromatic organic compound with the molecular formula C7H8N2O3: Appearance: A deep yellow powder;Melting point: 141°C; Density: 1.211 g/cm3 at 20°C; Solubility: Slightly soluble in water, soluble in alcohol, acetone, and DMSO; MNA is used in many applications, including:Textile dyeing: Used to dye cotton" on and on.
Not too shabby. To some extent the AI info makes me feel partially obsolete. And the above blurb is only some primitive form of AI, so one can only imagine.--Smokefoot (talk)
- If it's any consolation, WP is a prime source of training material for AIs, so they'll have been influenced by the tens of thousands of chemistry articles you've worked on. Preimage (talk)
- I've not used chat GPT for wiki articles but I can see how it might be useful. For example, I put the following prompt into GPT
- Can you suggest improvements to my next post which would make it easier to understand.
- And then copy and pasted in the TEMPO article. The suggested improvements weren't too bad. Some lot of our larger pages suffer from editors making many small changes which slowly degrade the overall readability of the article. AI can copyedit near instantaneously. Obviously, always double-check the output. Project Osprey (talk)
- The amount of pure chemistry bullshit even the "good" AI/LLM produce is astounding. Collegues and I have found it generates correct summaries of known correct material and correct answers where the answers are actually directly known in the corpus, but poor generalizations or even trivial extrapolation from known to close-analog unknown, and it is surprisingly poor at simple nomenclature. Many do train on WP content, and I was recently amazed how quickly a statement someone added to a WP article, that was uncited and likely nonsense based on logic and lack of any support by multiple other searches, became a touchstone part of a response to an AI prompt. So WP:CIRCULAR is just one of many caveats. I've seen it be useful for cleaning up prose, but only with an actually intelligent human carefully double-checking the meanings. WP as a whole is still grappling with policies and guidelines. DMacks (talk)
- One really important consideration is documenting the sources that are used to generate the AI text. Ask ChatGPT for sources to support the text it has generated, it will often invent (hallucinate) citations which is absolutely unacceptable in both science and Wikipedia. These invented sources often appear legitimate but are entirely fictional. Even when ChatGPT is confronted with hallucinations, it will continue to generate hallucinated sources. Perplexity at least will provide links to real sources and you can make your own judgment as to whether the sources support the text. Boghog (talk)
- I wouldn't trust it to make a new page from scratch, and doing so probably wouldn't save any time, since I would then have to verify every fact. To me its a Chinese room, so I don't think it really knows what a fact it - but its good with prose. I don't know what happens if its given references and told to stick to them. GPT will always tell you that is doesn't have access to proprietary databases or subscription-based content but I'm not sure if I believe it. I expect it has access to all sorts, but that its just hard-coded to say that it doesn't in order to stop people trying to use it as a back-door. Of course this is now - as Smokefoot says, one can only imagine. Project Osprey (talk)
- If you have access to the source pdf, you can upload it and ask the chatbot to summarize the entire article or portions of it. I think a reason that the chatbot states that it doesn't have access to proprietary content, even though it does, is so they won't be sued by the copyright owners. Boghog (talk)
- It is possible to train a bot to prioritize factual accuracy. If you ask Perplexity to find sources that support a verifiably false claim, it will do fact checking and provide sources that contradict that claim. Boghog (talk)
- ...although it won't always notice that the sources contradict the claim, I've noted. Jo-Jo Eumerus (talk)
- ...although it won't always notice that the sources contradict the claim, I've noted. Jo-Jo Eumerus (talk)
- If you have access to the source pdf, you can upload it and ask the chatbot to summarize the entire article or portions of it. I think a reason that the chatbot states that it doesn't have access to proprietary content, even though it does, is so they won't be sued by the copyright owners. Boghog (talk)
- I wouldn't trust it to make a new page from scratch, and doing so probably wouldn't save any time, since I would then have to verify every fact. To me its a Chinese room, so I don't think it really knows what a fact it - but its good with prose. I don't know what happens if its given references and told to stick to them. GPT will always tell you that is doesn't have access to proprietary databases or subscription-based content but I'm not sure if I believe it. I expect it has access to all sorts, but that its just hard-coded to say that it doesn't in order to stop people trying to use it as a back-door. Of course this is now - as Smokefoot says, one can only imagine. Project Osprey (talk)
- One really important consideration is documenting the sources that are used to generate the AI text. Ask ChatGPT for sources to support the text it has generated, it will often invent (hallucinate) citations which is absolutely unacceptable in both science and Wikipedia. These invented sources often appear legitimate but are entirely fictional. Even when ChatGPT is confronted with hallucinations, it will continue to generate hallucinated sources. Perplexity at least will provide links to real sources and you can make your own judgment as to whether the sources support the text. Boghog (talk)
This is the primary technology used to remove CO2 from other gases, but I can't find any structural diagrams that show the process. I wondered whether someone might be able to help out and make something very vaguely like File:Glyphosate_degradation.svg showing how CO2 is captured and then released from the amine? doi:10.1016/j.rser.2022.112902 has various equations in that could be used as a source e.g. in 2.1.1. Thanks! SmartSE (talk)
Are the chemistry templates preferred over raw HTML? I encountered an article with raw HTML chemical formulae and I wanted to see if there was any consensus on the preferred method. I would imagine that {{chem2}} would be preferred for maintainability reasons, but—again—I wanted to judge consensus before making any changes. Thanks, /home/gracen/ (they/them)
- I prefer the templates, except for the rare instance where there are so many that it causes the parser to break. But I don’t know if there is an official WP:MOS about this. YBG (talk)
- Don't use {{chem}} as it inserts extra characters that make the formula unsearchable or useless on a copy. But the worst is <chem> markup which uses a weird font and is also bad on copying. Please change that <chem> if you see it. Chem2 is good. HTML sub and sup are fine, so there is no need to change them. There are also some templates like {{CO2}} which seem OK. Graeme Bartlett (talk)
- I know there are some editors who strongly prefer using {{sup}} when writing isotopes rather than HTML. I am unsure if there is any MOS, accessibility, or quality article consideration for that, but I try to keep it to one standard if I see either. {{chem2}} is by far the best way to represent things you could otherwise use {{chem}} or <chem> for in the body of an article. Reconrabbit
- Another thing to watch out is where templates are used. There can be trouble when using them in references or as part of other templates. I will also comment, that if you don't change the appearance for the better in the final article, it is a time waster (busywork) for you and others who check, if you change existing articles. Also note that math markup may be used for complicated notations. But ⇄↑↓←→ all have their own Unicode that can be entered. Graeme Bartlett (talk)
- I know there are some editors who strongly prefer using {{sup}} when writing isotopes rather than HTML. I am unsure if there is any MOS, accessibility, or quality article consideration for that, but I try to keep it to one standard if I see either. {{chem2}} is by far the best way to represent things you could otherwise use {{chem}} or <chem> for in the body of an article. Reconrabbit
This template is intended to link to a search of Organic Syntheses to return all preps that mention a given chemical. However, Org. Synth. redid their website 11+ years ago, breaking the template. I flagged it 6 years ago with no response. The current site does not appear to give an easy way to link to a specific search. And it seems we (as editors) have never really been using this template anyway (there was only a single invocation of it, and it didn't even spell the chemical name correctly). Time to delete it? DMacks (talk)
- Sounds good to me. YBG (talk)
- @DMacks, please start a discussion at WP:TFD. I suggest that you quote this criterion, which is listed on that page:
- The template is not used, either directly or by template substitution (the latter cannot be concluded from the absence of backlinks), and has no likelihood of being used.
- wiki markup:
- The template is not used, either directly or by [[WP:SUBST|template substitution]] (the latter cannot be concluded from the absence of backlinks), {{Strong|and has no likelihood of {{em|being}} used}}.
- While WP:SUBST may not be easily verifiable, if what you say is correct, the subst-ed result would be useless. YBG (talk) 02:18, 10 January 2025(UTC)
- Wikipedia:Templates for discussion/Log/2025 January 10#Template:OrgSynth preps. Given this one's contents and stable history, it was easy to search for its content string to find subst's. DMacks (talk)
- Wikipedia:Templates for discussion/Log/2025 January 10#Template:OrgSynth preps. Given this one's contents and stable history, it was easy to search for its content string to find subst's. DMacks (talk)
- @DMacks, please start a discussion at WP:TFD. I suggest that you quote this criterion, which is listed on that page:
- Yes, delete it. Bduke (talk)
- I try not to cite Collected Volumes of Org Syn (OS). Its not a huge deal but the Collected volumes are not really a time marker like the original article.
- Here is a significant problem with OS: If one tries to access it through Wiley, a paywall appears (https://onlinelibrary.wiley.com/doi/10.1002/0471264180.os046.02 for 2,2'-Bipyridine) but if one accesses OS through the Organic Syntheses Corp, no problemo (https://www.orgsyn.org/demo.aspx?prep=cv5p0102). An imperfect explanation is that when it was constituted, Org Syn owned its content and made so much money on it that they made their content free to the world, but Wiley, who prints OS would rather that we go through them. Blah, blah, etc. The point is that the accessibility of OS articles depends on the pathway.--Smokefoot (talk)
- I didn't even realise Wiley was involved, I've only ever used the OrgSyth website. I suspect the template was created because the pages were historically awkward to cite - OrgSyth were late in adopting DOIs, so references had to be written manually. That isn't the case anymore. DOIs from OrgSyth do auto-convert into odd looking refs - but that's a pedantry up with with I cannot put. We can generate refs automatically which link back to the papers in question, the template is therefore redundant. You may fire when ready. --Project Osprey (talk)
- This template has nothing to do with citing refs, linking to preps by product-name or volume/page, or collected vs annual volumes. Sounds like you are thinking of {{OrgSynth}}? There are some cleanups related to that also needed, maybe we should start a new section with Smokefoot's comment. DMacks (talk)
- You are correct, I had misunderstood the question - but having reread it I think that one should be deleted too. Project Osprey (talk)
- You are correct, I had misunderstood the question - but having reread it I think that one should be deleted too. Project Osprey (talk)
- This template has nothing to do with citing refs, linking to preps by product-name or volume/page, or collected vs annual volumes. Sounds like you are thinking of {{OrgSynth}}? There are some cleanups related to that also needed, maybe we should start a new section with Smokefoot's comment. DMacks (talk)
- I didn't even realise Wiley was involved, I've only ever used the OrgSyth website. I suspect the template was created because the pages were historically awkward to cite - OrgSyth were late in adopting DOIs, so references had to be written manually. That isn't the case anymore. DOIs from OrgSyth do auto-convert into odd looking refs - but that's a pedantry up with with I cannot put. We can generate refs automatically which link back to the papers in question, the template is therefore redundant. You may fire when ready. --Project Osprey (talk)
Tumblr as a reliable source?
I noticed that Tumblr is being used as a source? Isnt that like citing Facebook?--Smokefoot (talk)
- That would be a very dubious source. However I suppose if it is a blog from a known expert that has published other acceptable materials, it might be useful. But it is not peer reviewed and so less acceptable than something published in a journal. Graeme Bartlett (talk)
General term for n-ary carbon?
I've been writing up some stubs for Simple English on chemistry topics, and have run into an unexpected wall: is there a general term for ordinals on carbon in alkanes (primary carbon, secondary carbon, tertiary carbon, quaternary carbon)? I don't think they really warrant separate pages there (honestly, maybe not even here?), but can't find a good overall title. As a mathematician, we'd use n-ary, but I'm not aware of that being a major thing in chemistry literature.
I want to call them "degree" - mostly because they're written with the degree symbol, but also by analogy to degree of substitution on heteropolymers - but I've not found an actual source for that handy. Is anyone aware of a proper term? Fishsicles (talk)
- I had the same problem writing the Polish article pl:Rzędowość. It turned out that what is most normal in other languages that this topic is always defined by one phrase (in Polish "rzędowość", in German "Substitutionsgrad" etc.), in English... such a term basically does not exist in sources. There are some terms in d:Q9325500 that users added, but I am not convinced whether they actually appear frequently in English-language sources. Wostr (talk)
- Degree of substitution seems right to me. Looks like this usage goes back at least to 1881. Would #1 count as a good enough source?
- Bünzli-Trepp, Ursula (2007). Systematic Nomenclature of Organic, Organometallic and Coordination Chemistry: Chemical-Abstracts Guidelines with IUPAC Recommendations and Many Trivial Names. Lausanne (Suisse) Boca Raton (Fla): EPFL Press. ISBN 9781420046151.
- Strecker, A.; Wislicenus, J.; Hodgkinson, W.R.E.; Greenaway, A.J. (1881). Adolph Strecker's Short Text-book of Organic Chemistry. K. Paul Trench & Company. Retrieved 16 January 2025.
- (with the caveat that methanol is considered a primary alcohol, despite having zero substituents: https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:15734)
- Preimage (talk)
- I suspect "nullary" compounds in general are just grouped as primary on the grounds that they're never going to be a whole family of compounds, and they're less far from primary than anything else. Much as it would be fun to torment the chemists in my life by asking if I can infer that water is a -1-ary alcohol...
- Thanks for the source, that'll work just fine. Fishsicles (talk)
This is picture correct?
This 2008 image is used at Pinacol rearrangement and several other pages, but on closer inspection the last step looks wrong to me. Chromium(VI) compound are powerful oxidisers but I've never heard of them achieving this sort of dealkylative-oxidation. What stays my hand is that the reaction is referenced (I cannot access the paper, and 18th Century German isn't my area) and it was made by V8rik, who was a competent editor.
Any opinions? Project Osprey (talk)
- Unless it's full oxidation to the keto acid, followed by decarboxylation and another round of oxidation? If so, I think the intermediates should be shown. Project Osprey (talk)
- Yes, that's correct, I think. Most ketones can be oxidised by acid dichromate: that was an industrial process for producing adipic acid from cyclohexanone according to my 4th edition of March, p.1176. So the reaction with pinacolone will be oxidation of its enol to the alpha-hydroxy compound and then further oxidation to give tBu-COCOOH and a final decarboxylation. Mike Turnbull (talk)
- Yes, that's correct, I think. Most ketones can be oxidised by acid dichromate: that was an industrial process for producing adipic acid from cyclohexanone according to my 4th edition of March, p.1176. So the reaction with pinacolone will be oxidation of its enol to the alpha-hydroxy compound and then further oxidation to give tBu-COCOOH and a final decarboxylation. Mike Turnbull (talk)
- Dichromate definitely shouldn't be oxidising a ketone on its own, which was my first read on the picture; that's one of the main empirical tests to check aldehyde vs ketone. Assuming it's still in the H2SO4, oxidative cleavage is an option, but it's definitely not a one step process like the image portrays. Fishsicles (talk)