User talk:Project Osprey/Archive 3

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Not sure it matters, but in case ...

 * Aww, that's really kind of you, it's always nice to have a pat on the back. --Project Osprey (talk) 12:18, 27 September 2015 (UTC)

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Eglinton reaction
Thanks for your continued help and contributions, which I enjoy reading. You might consider creating Eglinton reaction as a stand-alone article. It seems more important than the Cadiot... reaction. --Smokefoot (talk) 18:20, 10 December 2015 (UTC)
 * Seems better than the current arraignment. I think that the Cadiot–Chodkiewicz and Hey reactions should be merged into the Glaser coupling; they all look to be the same process, just with different counter-ions. I'll need to make sure the mechanisms aren't different though. Watch this space. --Project Osprey (talk) 11:50, 11 December 2015 (UTC)

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Mass merger of some surfactant pages
Hello Project Osprey,

I left you a message at https://en.wikipedia.org/wiki/Wikipedia_talk:WikiProject_Chemistry#Mass_merger_of_some_surfactant_pages in case you don't have this page on your Watchlist.

Cheers.

Georginho (talk) 14:20, 17 May 2016 (UTC)

sodium dithionite
Dear Project Osprey, Many thanks for all your excellent work for Wikipedia chemistry pages. I was reading the sodium dithionite pages, and noticed that the Em = -0.66 vs NHE. Should that be vs. SHE as I think it was in the original Mayhew paper? — Preceding unsigned comment added by Thmsclrk (talk • contribs) 21:29, 30 June 2016 (UTC)
 * Thanks for the note. Electrochemistry really isn't my area but he's using the nernst equation so I'm guessing that its SHE. I've changed the page accordingly.--Project Osprey (talk) 09:28, 1 July 2016 (UTC)

Fluoro-cannabidiols
Hi there. Saw you had PROD'ed these and User:Aethyta objected to it. After a quick read of the source article, I would say the 4'-Fluorocannabidiol (HUF-101) is just notable enough for an article, given the claimed increase in efficacy on all parameters and as there is not that much SAR research into cannabidiol as yet. The other two compounds though I do not think are worthy of stand alone articles as there was no increase in activity, indeed HUF-102 was actually inactive and the other one only slightly more active, so clearly any further research into this series will use HUF-101. The other two pages can just be redirects to that. Reasonable compromise? Meodipt (talk) 08:04, 23 August 2016 (UTC)


 * I guess. A lot of what you two work-on tends to be about designer drugs and I've always thought of them as being WP:MEDRS exempt - people are already taking them and that makes them notable compounds, regardless of how patchy the literature data is. The same argument can't really be made for these fluorocannabidiols; it's just primary research and the claims (based on a study of 20 mice) don't meet our usual standards for inclusion. Perhaps a solution for these sorts of pages might be to convert them into drafts? That way if they become more notable later on you already have a page that's half written. --Project Osprey (talk) 10:44, 23 August 2016 (UTC)


 * Yeah these fluoro cannabidiol pages are a stretch to claim notability for I agree. I'm not sure they would survive a formal deletion discussion. Still there are few enough CBD derivatives reported that any advance in the SAR is interesting, hence why I'd favour keeping the page for the most active compound. I certainly don't think three separate pages can be justified from one paper in the primary literature though.Meodipt (talk) 11:49, 23 August 2016 (UTC)


 * I didn't really have a chance explain it in the tiny edit summary, I objected the removal because of the reasoning "primary research on mice, not yet applicable to people", which didn't really appear to be a valid concern - Wikipedia isn't MedlinePlus after all, it shouldn't matter whether research is applicable to humans as we're not going to provide medical advice as per WP:NOMEDICAL anyway. WP:MEDRS, by definition, doesn't apply to designer drugs either (medicine = pharmaceutical drug != designer drug; can't give (bio-)medical information about something that isn't actually medicine). That being said, are there any issues regarding the quality of newer designer drug articles? I try to keep it as technical and neutral as possible, nothing encouraging, no description of effects other than well referenced side effects, and of course update the articles as soon as new information is released, from law changes to post-mortem case reports. Very, very different style compared to some of the ancient PiHKAL drugs with 3/4 of the page being subjective effects. Back on topic, inactive substances (no opportunity for future encyclopedic content) with a single reference aren't really notable; a legitimate reason for removal. Keeping HUF-101 around as a stub or even just draft (conclusions based on 20 mice are indeed not very convincing) sounds good, but the other two articles are a lost cause. While you're at it, mind deleting the crap that is Mary Joy? Aethyta (talk) 14:24, 23 August 2016 (UTC)


 * Thanks for getting in touch. The text limit for PRODing is also quite short and I didn't really make efficient use of the safe, so apologies for that. I have an general issue with a lot of phara-stubs that begin with: "Name" is a chemical compound which has been shown to have "medical effect" - because I think most people would read that and assume that it refers to people, whereas it's often initial research using mice or zebrafish or cell-line studies. Such compounds do feel much less notable when you point that out but deleting them remains a lot of work; these ones caught my eye because they were fairly new. I try to help out a with the designer drugs pages from time to time, mostly doing CAS look-ups and structure checks, so I'm aware of some the problems you have and I know they're things that we basically can't fix. I do wonder about the pagenames though, lots of them are just an alphabet-soup "AMB-FUBINACA (also known as FUB-AMB and MMB-FUBINACA)" is anyone searching for them under these names? --Project Osprey (talk) 16:04, 23 August 2016 (UTC)

I don't think that a compound is necessarily less notable because it is only used in animals (or indeed only in vitro), many research ligands are perfectly notable even though no one has any intention of ever developing them as medicines. Especially for obscure receptor targets that not that much is known about yet, I always try to make pages for the first ligand discovered for that target, the most potent ligand and/or the most selective ligand, and none of those early probe compounds end up being developed as medicines. It is certainly important to make clear when results are only applicable to animal models though. Regarding the designer drugs, I'm afraid we are rather stuck with this alphabet soup of compounds, some of which are systematic and some are just random codes. It doesn't help that the vendors selling the compounds often use a different code from what it is called by the analytical chemists that first report it in the literature, or that independent labs in different countries each come up with their own code and then insist on using that from then on. But yes I can assure you that people will be searching for these compounds by those odd names, at least for the more widely known ones anyway. Meodipt (talk) 00:01, 24 August 2016 (UTC)

CX717
Hi there. I noticed someone had added a CAS number to the page for this mysterious compound, which apparently the structure of has been kept secret since its discovery in 1996! The company have many patents and a few scientific papers published on the series, and CX717 itself has been through human trials for several applications with mixed results, but they seem never to have confirmed which of their dozens of example compounds it actually is. Anyway though if it is listed on CAS does this mean the structure is disclosed? I didn't think they assigned numbers to "secret" compounds. The listed CAS number 867276-98-0 seems commonly associated with a patent US 6110935 but a quick read through looks like this is the patent for an older compound farampator (CX691). I don't suppose you would mind looking this number up on the CAS registry and see what it says about it? Meodipt (talk) 08:36, 28 November 2016 (UTC)
 * I didn't think it was possible to do human trials without disclosing what the compound is... you'd of thought there would be ethical issues there. I'll look into it. --Project Osprey (talk) 09:35, 28 November 2016 (UTC)
 * This 2015 review notes that the structure has not been published, apparently due to DARPA restrictions. I'm guessing their interest might step from it's reported ability to hold off the effects of sleep deprivation? . I've looked at the literature post 2015 without luck, SciFinder also has nothing, ditto the DARPA website, so I guess we're going to have to wait. --Project Osprey (talk) 10:03, 28 November 2016 (UTC)
 * Thanks for trying anyway! Yeah DARPA's trials against sleep deprivation failed though, as did the trials against ADHD - ironically after decades of research and presumably millions of dollars in funding it appears the compound is only of a similar in vivo potency to the parent compound aniracetam, despite the claimed much higher potency in vitro. It was only the unexpected finding that these compounds also block the respiratory depressant effects of opioids without affecting analgesia that has kept the research going. Interestingly enough these days Cortex seems pretty happy to send out samples to researchers all over the place (presumably so fresh publications keep coming), its a bit surprising none of them have sent it off to be analysed but I can only assume there are some very stringent NDAs involved.... Meodipt (talk) 18:24, 28 November 2016 (UTC)
 * Well I for one would take an NDA from U.S. military quite seriously. I guess they just protected it for a set amount of time and that's still running, even if their interest in it has ended. --Project Osprey (talk) 09:19, 29 November 2016 (UTC)

Two things
Thats for now, --Smokefoot (talk) 16:24, 2 December 2016 (UTC)
 * Based on recent Talk on our mutual interest ethoxylation, I was thinking of moving this article to alkoxylation. I dont know if other epoxides are used widely, something to check on.
 * Ullmann's has a big section on fatty amines. So I might work on that topic.  As usual the even-numbered amines are more important.  Apparently made from fatty nitriles.
 * I replied at the article talk regarding the confusion between ethoxylation and alkoxylation. I'm not in favour of a merger. Ethoxylation is a large stand-alone industrial process and there is plenty to say about it. Ullmann's is already referenced at fatty amine, but if it has more to say that go ahead. For context, in surfactant chemistry fatty amines are less important than you might expect, they're invariable more expensive than fatty acids or alcohols and tend to by more harmful in the aquatic environment so their use as starting materials is somewhat limited. --Project Osprey (talk) 00:26, 4 December 2016 (UTC)
 * I foresaw your recommendation and did not try to merge ethoxylation. I did however add a short article on alkoxylation as a way to mention the EO and PO uses. Also I revised the lede to ethoxylation to make it clear that in principle one can ethoxylate stuff other than ROH.  I was thinking of amines. I have little direct experience with this area, but the topic has been a pet of mine since I sensed it was under-represented in Wikipedia relative to the role of these materials in commercial sphere.  --Smokefoot (talk) 02:52, 4 December 2016 (UTC)

Jahn-Teller
Well apparently I was wrong, the elite rewriters of Jahn-Teller effect never came back to reconcile their article that I took down. So I put their elegant but almost indecipherable version back up and merged in most of the older version as a preface. --Smokefoot (talk) 17:41, 24 December 2016 (UTC)
 * Well Christmas is a dead period for most people, so I hold a slender hope that they may return. Thanks for straitening out the merger and I wish you a happy New Year. --Project Osprey (talk) 00:01, 3 January 2017 (UTC)

Hydrogen Peroxide
Hey I wanted to talk about your comment on hydrogen peroxide talk page. I believe its completely wrong and I have numerous citations and examples proving otherwise. I was also wondering what reference material you had that said otherwise. Hydrogen peroxide is water in a higher oxidation state (True). The reduction potential for the half reaction between hydrogen peroxide and water is published in Descriptive Inorganic Chemistry by Calhoun and Overton (pdf free online). You can read my lengthy comment on the hydrogen peroxide talk page and respond there but I would like you to include references to where you information comes. Right now peoples opinions are confusing some of the wiki publishers and its upsetting me because there is no cited material to support their side of the argument but they are sure they correct. Could you help them find material that says hydrogen peroxide isn't water in a higher oxidation state? I'm supporting the other side of the debate and I have the numbers describing the half reaction for the oxidation of water to hydrogen peroxide. I am going to rewrite the introductory paragraph if no one has reference material to support your side of the debate in a week. Thanks for your time TerpeneOtto (talk) 17:25, 12 January 2017 (UTC)
 * Thanks for getting in touch. To keep things simple I'll reply at the article talk page. --Project Osprey (talk) 11:18, 13 January 2017 (UTC)

Dumbbell-shaped?
Hello, just thought I'd give you some fun grief. 'dumbbell' C22− ions? I confess to using the term in weaker moments, but what on earth does that mean? Its just two atoms, linked. Otherwise the following comments are not anything we can put in Wikipedia: I concur that M-C2H species might even dissolve in amines. It would be a shocker if the second pKa were below that of NH3. The real proof of salt-like for me would be an Xray structure of a salt like Na(crown)+C2 R. The term saline is probably mine, it is used in textbooks to refer to saline hydrides (NaH), and probably just extrapolated. Cheers,--Smokefoot (talk) 13:14, 2 May 2017 (UTC)
 * The term was new to me but I'd seen it twice while looking at the literature this morning and though it might of been one of those descriptive conventions that you see in some areas. Having looked for the term specifically it doesn't seem to be that common, I've taken it out. Definitions like ionic and covalent always seem to get a bit fuzzy when you're describing series like these but there does seem to be some sort of tipping point somewhere. --Project Osprey (talk) 14:00, 2 M ay 2017 (UTC)
 * We're both right probably. But I just dont see how a diatomic is usefully described as dumbbell shaped.  Maybe too picky. --Smokefoot (talk) 13:37, 8 May 2017 (UTC)

Ullmann says its a soap, I dont know though
Here's the TOC from Ullmann's chapter on "Metallic Soaps" .... Its not my idea and I was surprised by the terminology. Your friendly stalker. --Smokefoot (talk) 13:37, 8 May 2017 (UTC)
 * 4. Occupational Health and Environmental Protection . . . . . . . . . . . . 5
 * 5. Individual Metallic Soaps . . . . . . . 6
 * 5.1. Sodium Soaps . . . . . . . . . . . . . . 6
 * 5.2. Potassium Soaps . . . . . . . . . . . . . 6
 * 5.3. Lithium Soaps . . . . . . . . . . . . . . 6
 * 5.4. Magnesium Soaps . . . . . . . . . . . . 7
 * 5.5. Calcium Soaps . . . . . . . . . . . . . . 7
 * 5.6. Barium Soaps . . . . . . . . . . . . . . 8
 * 5.7. Aluminum Soaps . . . . . . . . . . . . 8
 * 5.8. Lead Soaps . . . . . . . . . . . . . . . . 9
 * 5.9. Copper Soaps . . . . . . . . . . . . . . 10


 * Depends on your definition I guess. I get there is a technical definition of soap which allows for counterions other than sodium (Li, Mg and Ca soaps are all insoluble, greasy and involatile, which makes good lubricants) but that's not the common use of the word, most people think 'soap = detergent'. Also, where does that technical definition end? Copper soap sounds weird enough but Barium soap really baffles me; I thought Ba2+ was essentially unknown in solution. --Project Osprey (talk) 14:00, 8 May 2017 (UTC)
 * These terms sound weird to us because we are trained academically. These things are huge commercially so far as I can tell.  That hidden world of industrial/commercial chemistry is a fascination of mine.  Not sure what you mean by "Ba2+ was essentially unknown in solution"  There are certainly aquo complexes of Ba2+.  If you are referring to barium soaps, my guess is that they are avoided because of the intrinsic toxicity of barium.  Also most soaps of course are not supposed to dissolve in anything.  They form micelles in the case of "cleaning solutions".  For their main app, greases, soaps are as thixotropic materials, where they are not supposed to dissolve.--Smokefoot (talk) 03:27, 8 August 2017 (UTC)

Pigment Yellow 10
Well I finally did some digging, and you were correct to be skeptical. The structure is different than the tautomer that I selected. Thanks, --Smokefoot (talk) 03:27, 8 August 2017 (UTC)
 * Good of you to double check. My understanding of these sorts of dyes (based on what was probably a single A4 sheet on an undergrad course that now feels a long time ago) is that they're photochromic, so both forms probably do exist. --Project Osprey (talk) 23:28, 8 August 2017 (UTC)

High quality refs needed
Such as for the addition at AD. Best Doc James  (talk · contribs · email) 17:34, 21 September 2017 (UTC)

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Women in Red World Contest
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C2 ligands
Take a look at the mini-draft at the bottom of User:Smokefoot/sandbox. Thanks, --Smokefoot (talk) 15:10, 23 December 2017 (UTC)
 * I see the new C2-Symmetric ligands page. It's a good start, Christmas is a busy time for me but I'll try to help out when I can. Regarding your proposed merger of Chiral ligand - I see what your getting at but I thing what it really needs is to be merged into an article on asymmetic catalysis. The creation of such an article is a big job but I might give it a go in the New Year. --Project Osprey (talk) 22:19, 26 December 2017 (UTC)

New angle on oxazolines
I recently ran into the class of compounds called DMOX, dimethyloxazolines, derived from carboxylic acids and 2,2-Dimethylethanolamine. Apparently DMOX are used to derivatize fatty acids for GC analysis. (Analytical shortcomings and other considerations related to the identification of biomarkers of dairy fat intake Gama, M. A. S.; Filho, H. G. B.; Bizzo, H. R.; Antoniassi, R. European Journal of Clinical Nutrition (2017), 71(8), 1022-1023). --Smokefoot (talk) 16:21, 18 January 2018 (UTC)
 * Cheers, I can't get into the paper I'm afraid (or much else these days) but I think I get the general idea. The technique would seem to have been around for a while . I guess it makes sense; despite often being listed as good protecting groups I've always found oxazolines to be very stable (although I was looking at ones on the ortho position of a phenol, which are especially stable), which is what you'd want for GC. Aminomethyl propanol also seems to be used quite a lot for making oxazolines, I guess just because it's cheaply available. Thanks! --Project Osprey (talk) 14:07, 19 January 2018 (UTC)