User talk:Project Osprey

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Valinol[edit]

You expressed interest in this stuff. So here's the article, fresh from a young student valinol. I will do the tidying up if you dont have time. --Smokefoot (talk) 02:25, 11 December 2012 (UTC)

Cheers. I've given it a quick once over and will likly come back to it over the next few days. Is this student one of yours? If so could you ask him to double check what's in the "Reactions" section - much of it doesn't make sence to me. For a start where the reaction with cobalt(II) chloride is mentioned I think they mean Phosgene. Also, while I don't have it to hand, I am familiar with that paper by Glorius and for the life of me I can't remember it involving oxazolidone chemistry (oxazolidine yes, buts thats quite different). Project Osprey (talk) 16:00, 11 December 2012 (UTC)
We're at the end of the term and the authors of these articles either get it or they dont, so I just trim mercilessly. At least we have a place holder. Thanks for your help.--Smokefoot (talk) 16:29, 11 December 2012 (UTC)

Oxidation number/ Oxidation state[edit]

Thanks for the response. Yes the articles are dire! I would be happy to collaborate with you, in the new year. Do you agree with a merge or do you think that a rewrite of both would suffice? Even IUPAC are a bit confused if you read the IUPAC 2005 red book [1] and the IUPAC gold book definitions, they are not quite in step. I am not sure what calculation rules examiners in US prefer, and I'm trying to get an answer on what is accepted in the UK.

Regards Axiosaurus (talk) 16:53, 21 December 2012 (UTC)

I've made a start with the re-write here (feel free to edit there). It seems that some of my earlier statements were wrong but there is still officially a difference based on the IUPAC descriptions. I'm open to a merger, but I think it might be best to get the description of oxidation number finished first and then decide based on what we've got? Project Osprey (talk) 23:42, 27 December 2012 (UTC)
Hi I have had a look at your draft. Yep you've gutted it. Good it needs drastic surgery! So far I've been gathering references and history. It's an old venerable concept widely used in inorganic chemistry rather than organic,and I am a bit taken aback by the amount of material I ma slowly gathering. Have you any thoughts as to what could be done with the oxidation state article? Oxidation number is defined in the IUPAC 2005 Inorganic naming recommendations differently from the IUPAC gold book. This confusion has been menntioned in J Chem Ed. by W.B Jensen from the university of Cincinatti who has also written on the history of the concept of oxidation state/number. Oxidation number gradually replaced the name "Stock number" in the naming of inorganic compounds following the IUPAC recommendations in 1940. The IUPAC 2005 naming recommendations are followed quite strictly in the US at high school level. The 2005 recommendations are in themselves confusing as they use the terms oxidation state and oxidation number interchangeably in the text, with no mention of coordination compounds being treated differently. Oxidation state and oxidation number are actually taught in Europe as being synomynous. Oxidation state being the most commonly used term. This is found in all of the european text books, although charmingly Wiberg and Hollemann give an alternative name of electrochemical valence, which I personally think is a bad name as redox potentials are not relevant to say combustion reactions and this is an area where the idea of oxidation state/number concept is useful as it unifies the non electrochemical concept with traditional views of oxidation and reduction. To calculate oxidation number IUPAC 2005 recommendation is a set of rules which are pretty much what appear in the current article. A common approach still in text books was to use electronegativity difference to determine which atom gets the electrons. The IUPAC gold book definition of oxidation number in coordination compounds (recommending removal of ligands with all electrons), is not widely followed, most text books appear to call this oxidation state. Axiosaurus (talk) 10:23, 26 January 2013 (UTC)
I think that to make this work we would need to clearly separate the two concepts. It would be nice if we could have oxidation number (OXN) apply specifically to coordination compounds and oxidation state (OXS) apply generally to everything else. I'm not sure we can back that up though, there are too many exceptions (e.g. salts), which doubtless is the reason for the confusion between the two terms. Perhaps the best we can do is describe the nature and origin of the confusion? It's not a very satisfying solution but frankly I'd stuck for how else to proceed. Do feel free in edit the article in my sandbox, I also suggest that we move the discussion to its talk page (I'll move the old conversions across to there at some point). Also of some concern is the number of pages which seem to have used either OXS or OXN to determine the electron configuration of metal atoms. This page is a good example (look at the molecular orbital diagram at the bottom).Project Osprey (talk) 12:19, 26 January 2013 (UTC)
Yes I agree I've come to that conclusion myself. I have reread all the IUPAC stuff- I thought the gold books were "up to date" but the definitions of oxdtn # and oxdtn state refer to the " Red Book: IUPAC Nomenclature of Inorganic Chemistry. Third Edition, Blackwell Scientific Publications, Oxford, 1990" and "PAC, 1990, 62, 2167. Glossary of atmospheric chemistry terms (Recommendations 1990)" respectivelly. Their latest naming recommendations Nomenclature of Inorganic Chemistry IUPAC Recommendations 2005 are different. Oxidation number is defined there as indicating the oxidation state of the central atom. Later it says that the oxidation number is used in naming compounds and the examples shown have no "central" atom. There is apparently a IUPAC project "Towards a comprehensive definition of oxidation state" started in 2009 but not published yet. I have realised that many mixed valence compounds in wikipedia are have incorrect IUPAC names. Fe3O4 iron(II,III) oxide, - however IUPAC 2005 says its iron(II) diiron(III) oxide- so they'll need putting right. I have drafted some stuff but I 'm not happy with it. As soon as I have something - I'll drop it on your sandbox.Axiosaurus (talk) 17:34, 2 February 2013 (UTC)
My version is here see what you think. In regard to the MO diagrams I think for the purposes of this we can set these aside- if you are being taught ligand field theory you are already (or should be) well conversant with the concept of oxidation number/state. Axiosaurus (talk) 15:43, 15 February 2013 (UTC)
Been ill and thinking a bit. Spectroscopic (physical) oxidation states - this topic, uopon which I am no expert!, I think relates to Non-innocent ligands- which I thought meant that the ligand doesn't have an obvious closed shell so removing it to give the "coordination chemistry oxidation number" of the complexed metal is tricky. Perhaps we should move this section to oxidation state as it has the words oxidation state in it. It could actually be an article in its own right eventually, but is very much a coordination chemistry topic. As for hapticity stuff , yes that doesn't really fit any more. Thinking ahead as to how we implement this change- some folk really object to replacement new articles so maybe a paragraph at a time. My latest version is here I've added a few more references. Axiosaurus (talk) 11:11, 1 March 2013 (UTC)
I have put it out as a complete rewrite. I have left the spectrocopic oxidation state stuff. Thanks for your input- hope the article is OK Axiosaurus (talk) 11:10, 7 March 2013 (UTC)
References

January 2013[edit]

Welcome and Happy New Year! Face-smile.svg[edit]

Hello, Project Osprey! Welcome to Wikipedia! Thank you for your contributions. You may benefit from following some of the links below, which will help you get the most out of Wikipedia. If you have any questions you can ask me on my talk page, or place {{helpme}} on your talk page and ask your question there. Please remember to sign your name on talk pages by clicking or by typing four tildes "~~~~"; this will automatically produce your name and the date. If you are already excited about Wikipedia, you might want to consider being "adopted" by a more experienced editor or joining a WikiProject to collaborate with others in creating and improving articles of your interest. Click here for a directory of all the WikiProjects. Finally, please do your best to always fill in the edit summary field when making edits to pages. Happy editing! 220 of Borg 01:48, 2 January 2013 (UTC)
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Personal note[edit]


I know you got a 'Teahouse Welcome', but that was a BOT, whereas I am a person, well mostly being Borg, (matter of definition I suppose? Face-grin.svg). You can of course delete the welcome if you don't need it, but please consider Archiving it instead. - 220 of Borg 03:43, 2 January 2013 (UTC)

Calixarene[edit]


As a person with chemistry knowledge could you please take a look at Talk:Calixarene#Discussion moved from article. Where newby editor C.David Gutsche (talk · contribs) (who is claiming great expertise in Calixarenes: "I am often referred to as "the godfather" of calixarenes and am one of the principal investigators in developing the calixarenes. C. David Gutsche" ), made an edit that needed a lot of clean-up and which was 'moved' to the talk page pending cites/re-write as required. Regards, 220 of Borg 03:43, 2 January 2013 (UTC)

I've never worked with calixarene's but I am familiar with some of the surrounding chemistry; so I can tell you that what he's written makes chemical sense but I can't tell you if its true or not. Citations are needed and that may prove a problem as I don't have free-access to scientific journals ATM (they're pay-walled). I'm not unwilling to work on this but I may not be the best candidate either, it would take me a good while to sort out. Can I suggest that you contact Wikipedia:WikiProject_Chemistry and leave a request on their talk pages? If no one else comes forward I'll do what I can but there should be someone there who is better suited to this.Project Osprey (talk) 12:22, 2 January 2013 (UTC)

Copper hydride[edit]

Put my two pennuth in as they say, but I suspect that PP is not for moving. Interesting compound, the only trans. metal hydride made from solution. The stability I suggest may in part be caused by the difference in close packing of Cu in metal and hydride. The article looks wrong, PP I think is quoting a Shriver paper about pyridine solutions, theres no ref, I'll flag it and see if he has one. Well CuH is a weird one, never come across it, I'd lumped all the t.metal hydrides together as brittle boring and grey. A brown / red t. metal hydride with aqueous chemistry! Looks like a freak compound formed from a H2O.Cu hydride complex drying out. If they hadn't done a structure determination on it I wouldn't have believed it. Something new every day.Axiosaurus (talk) 16:58, 8 March 2013 (UTC)

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Racemates and angry anons[edit]

To Project Osprey (Phd chem)!, (where do I begin?) 1) My issue was obviously nothing to do with biological activity. 2) Resolution is a term applied to the separation of optical isomers (enantiomers) NOT (cis-trans isomers), which may be separated much more easily. 3) My rage stemmed from a long history of trying to explain this (VERY BASIC) concept to many editors that obviously did not understand the simple logic of the issue. Maybe I assumed a higher degree of understanding than I should have when trying to express my point.--OneMadScientist (talk) 02:32, 8 May 2013 (UTC)

In responce to your repeated questions. In the statement "the trans isomer is reported to be more active than the racemate" I assumed that whoever had written it had ment 'racemate' to mean all 4 enantiomers of Cypenamine. If you think of it that way it does make sense, as the statement means "the trans isomer is more reactive than the cis isomer". I know this is not the correct way of writing it but it does make sense to me. Project Osprey (talk) 13:31, 9 May 2013 (UTC)

"My repeated Questions" You are really getting on my nerves. You have an unjustified smart ass attitude, toward me a least. Very strange Incorrect and incoherent things seem to make sense to you (and thus you argue they are correct) while clearly stated logical, recognized and accurate scientific principles, that "I kick up a fuss about" seem to not. Please for the sake of your own reputation think more than twice and get your facts in perfect order before trying to argue or challenge any point with me again. I assure you, you are out of your league. Do you want me scrutinizing all your contributions, and critiquing them, really do you, I don't think so. And still no clarification on your education qualifications and frankly even if you did have a chem phd it would not change a single word I said. Sorry but you asked for this and here you have it. You have been warned, as you guys like to say!--OneMadScientist (talk) 21:08, 9 May 2013 (UTC)

Actually, I'm quite happy for you or anyone else to edit my contributions. That's how wikipedia is supposed to work. Regarding Cypenamine: the situation has now become ridiculous. Please go to that page and make your 1 byte addition; a '+' or a '-' whichever you feel is right. Project Osprey (talk) 22:08, 9 May 2013 (UTC)

Yes you and others have caused this to become ridiculous. That 1 byte addition you condecendingly sugest as my meager contribution to this article adds actual meaning (in whatever context is was refering to? - again separate issue) to the statement and is more important than all the words and strange ideas you have had to say on the subject. If I need to go through this,over and over, due to the repeated misunderstanding of such a simple point I am surprised and appalled. How may times, and in how many ways, do I need to explain this, with MY perfect coherency, that my issue has nothing to do with any type of biological activity whatsoever. I do not care to even engage in discussion or research of aspects related to the exact specifics of the reaction or binding affinities of the different enantiomers of either of the cis or trans diastereomers, with enzymes, dopeamine receptors or whatever else. It is not an issue that I was commenting on. My issue has always been one of (structural naming, designations only) and that the particular statment in question has in fact no meaning in any way unless a specific enantiomer is specified. That's all, its very simple, and which one is best as recreational drug or laxative or whatever I was (so very obviously) not ever questioning.--OneMadScientist (talk) 09:17, 10 May 2013 (UTC)

I'm not actually trying to argue with you here. Your concern is that it doesn't make much sense the way its written, my concern is that it may not be true the way its referenced. These concerns are not in conflict. You act like I'm defending the way it was written, I am not. All I said was that I thought I understood what it was trying to say - I feel I'm allowed that. The sentence in question has been removed anyway, so I suggest we stop here. 10:05, 10 May 2013 (UTC)roject Osprey (talk) 09:37, 10 May 2013 (UTC)

Oh my god!, for the love of Christ! Please stop, I cant bear it, You seem to be completely unable to learn. I will no longer respond to any of your posts as it is futile. Except In the unlikely event you ever realize how completely right I am and wrong you are and apologize. You have defended the way it was written and contended it did make sense in relation to some issue, (this is in the record's). What YOU THINK in this context is irrelevant. For the last time, It Does not ("not make MUCH sense") It 100% IN ANY ACTUAL CORRECT CONTEXT WHAT SO EVER (except in your mind) MAKES NO SENSE I REPEAT AGAIN, NO SENSE WHATSOEVER. OK FINISH--OneMadScientist (talk) 10:07, 10 May 2013 (UTC)

May 2013[edit]

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Lead paragraph[edit]

I saw your edits to triisopropylamine. You might want to ask around. My feelings, which I think are shared, is that the lead should start v broadly with a very general classification of a compound as organic, inorganic, or whatever. A nonchemist just is not going to know what a tertiary amine is. I am sympathetic to not duplicating information in the chembox, so for this reason we give the structural formula, not the empiracal one. Structural formulas are not possible for lysergic acid but for phenol, one could have C6H5OH wihch is more informative than C6H6O. I also like the idea of one sentence that tells the reader what something looks like, e.g., "Phenol is a white volatile solid." You might consider describing your recommendations at the Chemicals talk site. BTW, thanks for your contributions with Europium(III) chloride. --Smokefoot (talk) 12:47, 15 May 2013 (UTC)

Sorry. I had to go and do some work and as the computers here power-down out after a while I could either save or start over. Normally I dump what I'm doing into my sandbox and finish it later but what I had made sense so I just pushed it through. I shall endeavor to be more conscientious in future.
I’ll be revisiting the page anyway, the synthetic prep is genuinely terrifying. Project Osprey (talk) 14:49, 15 May 2013 (UTC)
Hey I was not implying that you are not conscientious! I was just wondering if you were about to open up a broader conversation on the lead (or lede, not sure the right word). --Smokefoot (talk) 17:26, 15 May 2013 (UTC)
Don't worry! I didn't think that was what you were implying. Lead has been fleshed out although I still need to find a better method of production. Regarding the EuCl3 page: If you're happy with what's there then I'll start adapting the prep for the other rare earths (oxide and chloride pages). I'll probably also copy the silylamide prep across to the chloride pages - as it's also pretty universal. Project Osprey (talk) 15:01, 16 May 2013 (UTC)

Ln[edit]

  • Thanks for your note on catalytic oxidation.
  • The new catalysis section in lanthanide seems to mainly cite academic work. Nothing wrong with merely academic work except when portraying results of such papers as "useful". That adjective seems like a hyperbole.
  • Here is one lead on what looks like a commercial hit (described by academics but done in industry, per usual): "Neodymium-Based Ziegler/Natta Catalysts and their Application in Diene Polymerization" Lars Friebe, Oskar Nuyken and Werner Obrecht Advances in Polymer Science, 2006, Volume 204, Neodymium Based Ziegler Catalysts – Fundamental Chemistry, Pages 1-154. I understand that getting a good handle on commercially useful Ln catalysis is challenging. My guess is that most is heterogeneous. --Smokefoot (talk) 12:24, 3 June 2013 (UTC)

Hey, the section was mostly an attempt to generalise their coordination chemistry and catalysis just seemed a nice way of summing up their properies in a way that you could compare with more familiar coordination compounds. For top-level pages I try to provide some sort of context - brevity is only good when it makes things clearer. That said I don't own the page so if you want to thin it out then edit away. I'm afraid you're right about the lack of commercial/industrial uses. I'm not aware of any large scale examples of the coordination compounds being used as catalysts. There's a section on heterogeneous catalysis lower down, I'll see if your ref can fit in there (cheers for that btw). I'll see if I can find an industrial ref though, perhaps Org. Process Res. Dev. will deliver. Project Osprey (talk) 12:56, 3 June 2013 (UTC)

The section is very nicely done, and nicely described about the lability and geometry. With regards to the Shibasaki and Molander citations, the practical problem is that once a reference is inserted, it is difficult to remove or replace it without howls of "content removal" from other editors. And naive readers/students will, for eternity, suffer under the delusion that such work is actually useful for something other than publishing papers in JACS and Org Lett. Then they get to the real world and discover otherwise. I am being slightly exaggerating here, Monday morning and all that.--Smokefoot (talk) 13:39, 3 June 2013 (UTC)

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Zinc(II) hydride[edit]

I trying to improve this article, using acetic acid as a model, since it (acetic acid) is in the process of being made in to a FA article. It would be appreciated if you could have a look at the progress. Plasmic Physics (talk) 04:46, 11 June 2013 (UTC)

This could be a challenge. Discounting miniscule amounts made by lasers - no one seems to have made this stuff for more than 20 years. I'll see what I can do though. Project Osprey (talk) 11:55, 11 June 2013 (UTC)
Are you talking about the molecular form or the standard form? Despite the article claiming that it is used as a reducing agent in organic synthesis, I can't find any sources confirming or denying. Maybe you'll find something I've missed. Plasmic Physics (talk) 14:00, 11 June 2013 (UTC)
Standard form - I tend to think of that as being more important. I've seen books state that it's a reducing agent but so far I've found no real examples. I wouldn't be surprised if it worked - the question is why would you use it? You need a reducing agent to make it, so it just represents extra steps. If might be useful in some exotic process but overall it sounds pretty useless. I'll keep looking though. Project Osprey (talk) 09:48, 12 June 2013 (UTC)
Perhaps, it is because it is a cleaner reducing agent, it doesn't contaminates the product with lithium and aluminium salts, only zinc salt, and I do believe that zinc is easier to precipitate out.

I'm also trying improve Mercury(II) hydride. It's a slight bit more interesting as well, though less stable. Metal hydrides in general are difficult to figure out, considering that they come in three flavours: ionic solids, network solids, and molecular solids, and it doesn't help that they decompose into metal-hydrogen alloys, which aren't even compounds. Many sources fail to distinguish between them, such as with titanium hydride. A metallurgical paper that investigates the alloy, calls it titanium hydride, another paper by Lester Andrews that investigates the molecular form, calls that titanium hydride. Metallic hydrides, as the alloys are called, are dark grey, or metallic in appearance, while the network and covalent solids, vary between white, colourless, and even red for copper hydride. Earlier, the confusion over the nature of hydrides, lead me to erroneously believe that the copper hydride article was about the alloy. That is why I was involved with a debate about the article. Now I know that both forms exist, that is, the alloy, which is copper coloured, and the network covalent solid, which a red solid. On the topic, is there really a difference between ionic hydrides and network hydrides?

On another topic, do you agree that Mercury(I) hydride should be merged into Mercury(II) hydride? Since, it is so intensely unstable compared even with HgH2, and is in fact a decomposition intermediate of HgH2. I didn't think that it was notable enough to merit its own article when it was created, and I still don't think so. Plasmic Physics (talk) 11:43, 12 June 2013 (UTC)

I'll stick with the zinc hydride for now. It looks to be the most stable of the first row transition metal hydrides, so I figure it merits some attention. (perhaps we should create a category for all of these?)
Metal hydride alloys confuse me. I can’t help but think of them as matrix isolated metal hydrides in metal but I’m conscious that the hydride probably has all sorts of quantum effects (particle in a box and so on) not to mention effects on grain size and shape etc. I’m content to leave those pages to people who know what they’re doing.
My feeling is that T-metal hydride bonds are somewhere midway between ionic and covalent and at this point network descriptions break down somewhat.
Regarding the mercury hydride pages: Honestly, I think that different compounds should have different pages. Even if one of those pages is likely to remain a stub. However there’s no reason why the pages can’t be closely linked, currently Mercury(II)_hydride doesn’t mention Mercury(I)_hydride at all.Project Osprey (talk) 15:00, 12 June 2013 (UTC)

LiNtms2[edit]

Well that was strange, but I had been following your many edits and decided to take action. Best wishes for your continued contributions, which are v useful. --Smokefoot (talk) 22:04, 30 June 2013 (UTC)

No worries. It's always good to have someone check over your work, I'm sure I make more errors than I realise. Project Osprey (talk) 22:57, 30 June 2013 (UTC)

3-Methyl-3-octanol[edit]

Which section in the MOS applies? Plasmic Physics (talk) 11:31, 21 July 2013 (UTC)

See here. My understanding of this, is that if it's a famous piece of work or something that lead to a Nobel Prize (or some such) then fair enough, otherwise leave it out, because the information is in the references anyway. Project Osprey (talk) 11:48, 21 July 2013 (UTC)
I see. Plasmic Physics (talk) 12:01, 21 July 2013 (UTC)

Metal halides[edit]

Nice to see you getting involved in basic inorganics, we have a shortage of level headed editors in this area. An article was produced on K2TaF7, which is the central compound in the production of Ta and also relevant to the separation of Nb and Ta, somehow. But that heptafluoride compound remains obscure in textbooks. We did an article on NbOCl3, a problem in NbCl5 chem. although it appears that TaOCl3 is less of an issue because it readily converts to Ta2O5 and TaCl5. I have not found its X-ray structure. One of these years we can pursue this minor point.

Finally if you are looking for a good (secondary!) source of preps, the bible in that area is Brauer's "Handbook of Preparative Inorganic Chemistry", also in English. For binary and ternary compositions of important stuff, this secondary source has almost every compound with good historical context. I found a free copy online, slightly creepy but useful.--Smokefoot (talk) 14:39, 25 July 2013 (UTC)

Cheers for the advice. I feel I should warn you that these recent edits haven't been done out of any concious decision to focus in on inorganics - I just happened to find myself on those pages. That said, I'll see if I can add anything to the K2TaF7 and NbOCl3 articles once I'm done with my current project. Just so long as I don't have to look at T-metal hydrides again.
I actually have very little access to literature and mostly rely on what I can tease out of the internet for free (which is a surprising amount, if you're willing to put the time in), so directions to good open access books are very welcome.Project Osprey (talk) 23:14, 25 July 2013 (UTC)
The K2TaF7 and NbOCl3 articles dont need any particular help: I brought them up only because they are connected to your TaOCl3/TaCl5 interests. Re the hydride articles, wacky and mediocre but the ones being tinkered with are fairly obscure. Good luck finding Brauer. --Smokefoot (talk) 00:54, 26 July 2013 (UTC)

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August 2013[edit]

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There are 24556 references to Ta2O5....[edit]

According to CAS,there are 24,556 citations to Ta2O5. I am wondering on what basis did you select the new 20ish refs in your rewrite? Some are extremely narrow.--Smokefoot (talk) 12:55, 11 August 2013 (UTC)

I was debating flagging this for an experienced inorganic chemist (Axiosaurus?). I must admit, I found it difficult to write the structural section, as Ta2O5 seemingly has no regular structure. You might expect that this would lead to a well cited review on its structure and properties... but I searched for one in vain. Failing that all I could think to do was describe the limits of it's variations. There are several references I'm not entirely comfortable with: the single crystal analysis (doi:10.1524/zkri.1969.129.5-6.365) seems weak (Pna2 isn't even a real space group, I assume it's meant to be Pna21) but it was the only single crystal analysis I could find. I don't like that the chembox is showing the U3O8 structure (see talk page), as even if the atoms are in the right place the stoichiometry is wrong. In my defence the structure section was using a single 66 year old book as a reference - and for all that its secondary I'm not sure it's still right. I'm not possessive over my work though, so if you want to gut it then go right-ahead. Project Osprey (talk) 13:43, 11 August 2013 (UTC)
Re: your focus on crystal structures - a really important theme that many articles lack. For my money, the focus should be on the connectivity and bond distances/angles for the various polymorphs. Much of this information one can dig up via Googling, as apparently you are doing well.
I do worry about your inserting lots of specialized references to "junk" journals (Journal of Electroanalytical Chemistry and Interfacial Electrochemistry, Thin Solid Films - these are second-rate journals) may ultimately do more harm than good, because the naive reader will think that these junk sources are somehow authoritative (impressive sounding titles) and true experts, when they come to the article, will be loath to replace or delete these references from an article lest they be accused of vandalism. One additional reason for reliance on secondary sources is for editors like us who are writing about topics where we are not expert.
Good source of structures: The bible is Wells. A good source of images is the German wiki. Ideally you can gain access to the Karlsruhe inorganic crystallographic database. That is the best possible source for species lacking C-H bonds. Thanks for responding. Cheers, --Smokefoot (talk) 14:57, 11 August 2013 (UTC)

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Halide pics[edit]

Hi, Osprey, thanks for adding those pics. I'm not allowed to touch the chemboxes, so could you please shrink them down to 50px? Plasmic Physics (talk) 13:17, 15 August 2013 (UTC)

I'm just saying, not every pic in a chembox needs to fill all the space reserved for it; that, and you're less likely to be undone by the other members of the Project. Plasmic Physics (talk) 13:27, 15 August 2013 (UTC)

Awesome! Plasmic Physics (talk) 13:30, 15 August 2013 (UTC)

Done! (As you seem to have noticed). I see that you're doing some edits to flouride at the moment, if you have the time I think that page should contain flouride's ionic radii, electron configuration and redox potential. These are the basic properties that define its chemistry and I find their absence puzzling. (Why aren't you allowed to edit chemboxs?) Project Osprey (talk) 13:59, 15 August 2013 (UTC)
I'll address those things. It's hard to keep track of why I banned. I used to maintain chemboxes, making adjustments to parametres, trimming off code excess, filling in missing field data and correcting some. I spent my hour turning random chaos, into ordered chaos. At one point, someone complained that my edits are too trivial and just clogs up their watchlist. Another time, someone complained that I make too many typos. (I used to have a large work load, so it only makes sense that my typos are in proportion.) A sticking point seems to be nomenclature, that problem has evolved over time. The short story is, the ChemProject assumes that it is perfectly OK to question the systematic names which I add, but the courtesy is not returned. I tried to juggle every Project member's own personal mode of operation, and failed on all accounts as one demanded exactly what the opposite of the other. So, the Project's failure to reach consensus upon chembox guidelines and regulations, and lack of commitment to the cause of the Project itself, resulted in their only consensus - to illegitimately ban me from editing chemboxes at all. Despite showing my willingness to cooperate fully, they still called my edits disruptive, and acted accordingly. I even have my very own arch nememis: Smokefoot. Although, I have to say, the sentiment is not mutual, I wish he would just let me go, and get on with his wikilife. The Project is really just a club for chemists who like to edit chemistry related aticles, I can do that any day without being a member of a Project. A project is supposed to act in a cooperative way to organize and direct the development of relavent articles, categories, etc. Plasmic Physics (talk) 14:39, 15 August 2013 (UTC)
Anyways, what ionic radius do you want: crystal, or effective, or solvation shell; and which redox potential do you want: aqueous, molten, acidic, basic, atomic, elemental; and how do I relate this data to fluorine in a way which is unique to fluorine (there is no point in saying something which is true for all or most ions)? Plasmic Physics (talk) 10:41, 16 August 2013 (UTC)
  • I was thinking something along the lines of the Iodide page. Some basic properties, put into context by comparison against other halides, nothing too technical. The page gets a 1000+ hits a day and I think it’s safe to say that little of that traffic comes from experienced chemists. I always feel that we should cover the basics on pages where there's likely to be a lot of lay readers. (One of these days I'm going to buy a child’s book of science to use for pages like this one. Sounds a bit nuts I know but I think it would help).
Regarding other matters: To be fair, I have seen you come-up with some incredible names, tri-μ-hydrido-pentahydrido-1κ3H,2κ2H-dititanium for instance, but you won’t be the first person I've seen criticise Smokefoot over his (her?) manners. I have to say that Wikipedia isn't anything like what I expected. I thought we'd have 1000's of unregistered users making occasional but useful edits, kept in check by a hardcore of maybe a couple of hundred registered chemists. Instead WikiProject Chem has what? A dozen active members, 20 at the outside? Somedays I’m impressed that we manage to hold things together – sometimes I’m not sure we are holding things together. Anyway, regarding chembox's specificaly: should you find stuff that need doing, by all means drop me a note here and I'll try and sort it out for you. Project Osprey (talk) 12:27, 16 August 2013 (UTC)
Well, that particular example may be incredible, but it is certainly correct. The Project demands that I cite every systematic name I add, and at the same time they admit that systematic names inherently uncitable, due to the lack of a reviewed record of such names. Thus, I face a paradoxical situation: I can only add cited names, but no sources are acceptable. I don't know, maybe they have a superiority complex linked to their distinguished academic achievements. I really need an arbiter to solve this dilemma, to dissolve this aura of undue exclusivity. I need to know what their qualms are exactly, so that I can edit freely in good faith, and not have to guess who will I be offending next. I need guidelines/rules to follow, by which the Project will no longer have an excuse with which to persecute me.
Even so, I am grateful for your offer - it will be most useful.
Regarding fluoride, since it is now ~1:55 AM locally, I will review your suggestion tomorrow evening (locally). Plasmic Physics (talk) 13:57, 16 August 2013 (UTC)
  • Re: Systematic names. I have on occasion faced a similar dilemma - Sometimes you'll be faced with something hugely bizarre or unwieldy. I don't really have a definite rule for those occasions but I generally follow the following reasoning:
To me, a name is what you call something. So if I can't find an example of the systematic name being used - it's no longer really a name. At this point its more of a structure-based algorithmic data token, like SMILES or InChI. Except of course you can't use it to find more information on that compound. In those situation I tend to omit it; because while it is a fact, it isn't a useful fact and I like to think that the chembox is only concerned with useful facts. This also applies when I find more than one reported systematic name, which happens a fair bit with PubChem and ChemSpider. The naming system seemingly has its limits and different computer programs will occasionally give different answers. Under those situation I omit because I don't want to introduce errors. Project Osprey (talk) 09:15, 17 August 2013 (UTC)
If the reader understands systematic nomenclature, then they can easily derive the molecular structure without needing to translate the algorithmic token with software. Otherwise, is the systematic name ever useful? At first, I just added the systematic names, then I started citing them when the Project complained, then I stopped using chemical merchants as sources when they complained about that, finally I stopped completely when they started to complain about me using PubChem, Chemspider, and other databases. They also excluded CAS, journal articles, and textbooks thereafter. While there may be several technically correct names, the most concise and informative name is preferred by IUPAC. I construct the in-article additive names myself, to ensure that it follows the correct regulations to the letter (pun intended). Funny thing, the Project even rejects IUPAC's very own publications as sources for IUPAC names. The chembox names which I added, all actually had examples of use. Here is an example of the quality of the work that I used to do: http://en.wikipedia.org/w/index.php?title=Acetylcysteine&diff=470414146&oldid=468731738] Plasmic Physics (talk) 12:15, 17 August 2013 (UTC)

Thanks for J-T correction[edit]

Well, I should have known since Fe(III) is high spin. Nice catch. --Smokefoot (talk) 23:08, 27 August 2013 (UTC)

Bisulfide[edit]

Could you please add this ionbox to Bisulfide: User talk:Plasmic Physics#Bisulfide ionbox? Plasmic Physics (talk) 08:13, 4 September 2013 (UTC)

Sure, although I'm not too keen on using additive nomenclature in this instance. IUPAC recommend that for coordination compounds, which this clearly isn’t. Project Osprey (talk) 12:07, 4 September 2013 (UTC)
Do as you think is right, but IUPAC uses the definition: "A coordination entity is an ion or neutral molecule that is composed of a central atom, usually that of a metal, to which is attached a surrounding array of other atoms or groups of atoms, each of which is called a ligand." It goes on to mention "heptaoxido(phosphorussulfur)ate(2−)" as a coordination ion. Plasmic Physics (talk) 13:18, 4 September 2013 (UTC)
I just thought that perhaps, some reader somewhere will want to know the additive name for this ion. Plasmic Physics (talk) 13:22, 4 September 2013 (UTC)
If it was up to me I'd call it sulfidohydrogenate(1−) (or hydridosulfate(1−)), but IUPAC lists the given name specifically. Plasmic Physics (talk) 13:31, 4 September 2013 (UTC)
  • I can see you're point there, but to my mind the whole point of systematic names is that you end up with one name. Either way its up now, if anyone feel strongly doubtless they'll change it.Project Osprey (talk) 15:37, 4 September 2013 (UTC)

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First row t metal hydrides[edit]

thanks for that. Yes its all kicked off again - fun and games indeed at binary compounds of hydrogen. I have reworked the oxidation state page it is here at User:Axiosaurus/draft1 feel free to have hack at it. Dirac66 may be in there too. All improvements welcomed before it is tranferred back into Wikipedia proper. Regards Axiosaurus (talk) 18:59, 19 September 2013 (UTC)

Gallane[edit]

I have a chembox to insert on my talk page for gallane, if you don't mind. Plasmic Physics (talk) 09:35, 23 September 2013 (UTC)

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Wikibreak[edit]

I'm going to be taking a wikibreak for the next couple of weeks or so. Feel free to leave messages but they wont be read untill after I get back. Project Osprey (talk) 12:50, 24 September 2013 (UTC)

Gallane[edit]

You may be interested in the "amphotericity" debate I am having in "Weird Properties".Talk:Gallane Another POV would be welcome.Axiosaurus (talk) 08:27, 18 October 2013 (UTC)

  • Alas, I'm still on a partial wiki-break. I recently moved house and wont have internet access there for another 2 weeks or so. That being the case I don't feel that I can participate in this to any meaningful extent... that said, I still think that it reacts more like a hydride. Much like borane and aluminium hydride in-fact. I don't believe anyone refers to them as amphoteric. Project Osprey (talk) 12:06, 18 October 2013 (UTC)
Enjoy the move. Moving house is like being beaten around the head with a wet fish....a relief when it is all over. I shall continue debating and perhaps in the fullness of time, when/ if there is no resolution you can join in the fun. Axiosaurus (talk) 13:52, 18 October 2013 (UTC)

phosphates[edit]

See my talk page for a reply. Petergans (talk) 10:47, 21 November 2013 (UTC)

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It doesnt exist as a monomer[edit]

Showing monomeric LiNtms2 is equivalent to showing molecular NaCl, at least in my book. I guess is some vacuum experiment it might exist but there is this thing about reality....--Smokefoot (talk) 10:08, 8 June 2014 (UTC)

@Smokefoot: we've had this issue a few times with aggregating organometallics. Perhaps we should try and settle it? I do see where you're coming from, really. It would be silly to not show the trimer but not showing the monomer doesn't sit well with me either. I have 2 issues really:
  1. No one draws it like that. If you were drawing a reaction mechanism you'd use the monomer, all the texts books I have discuss its reactions in terms of the monomer (although they of course mention aggregation) and if you were to ask 10 chemists to draw the structure I'm confident the monomer would dominate. There's a clear convention there and wikipedia is supposed to reflect things like that.
  2. The image in the chembox doesn't correspond with various details in the chembox (formula, mol wt, etc). I don't like that, I worry it'll be a point of confusion to lay readers. Having labelled images of both forms gets around that.
I'm not advocating the use of one image instead of the other, I just feel that both are valid.Project Osprey (talk) 11:50, 8 June 2014 (UTC)
"No one draws it like that". I can see your point. Most people (=undergrad-trained chemists) of course are pretty naive about structures of polar organometallics. Maybe you should raise the issue at the Chemistry Talk page since, like you indicate, we have an unacceptable disagreement between the Box and the Image. The immediate issue is how to represent polar organometallics, but one can imagine someone insisting on representing TiO2 as a triatomic because such as species has been generated and examined by DFT. My recommendation: non-existent but convenient structures be represented only by ChemDraw, and representations of more commonplace structures be represented both as ChemDraw and other fancier ways. Thanks for responding so constructively. I will revert my revert now. Cheers, --Smokefoot (talk) 01:05, 9 June 2014 (UTC)

July 2014[edit]

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It's pyramidal[edit]

Greetings. Pretty sure that sulfite esters are pyramidal, so if you still have your ChemDraw, you might pucker the S. --Smokefoot (talk) 23:28, 1 August 2014 (UTC)

Sorry, I'd found it on wikimedia but there's already a better one to replace it with. If you actually want the lone pairs shown explicitly then we'll have to make that image ourselves. Project Osprey (talk) 09:59, 2 August 2014 (UTC)

NFPA[edit]

As you did with Sodium borohydride here, could you do that to Sodium cyanoborohydride? It too has an NFPA issue. -DePiep (talk) 00:21, 11 September 2014 (UTC)

Done. Project Osprey (talk) 10:59, 11 September 2014 (UTC)

P3N5[edit]

Just read your contribution to Smokefoots question about primary souurces etc. ,saw that you had written the P3N5 article. I have the latest German Wiberg at home and this has a reasonable section on P3N5 with a detailed description of the structure of the alpha and a briefer description of the gamma as well as stuff on other binaries. If you feel your german is up to it I could let you have a scan of the relevant sections. By the way my german language skills are rubbish, restricted to swearing and ordering beer. I rely on Google translate for anything else. Best wishes. Axiosaurus (talk) 12:18, 23 October 2014 (UTC)

Thanks for the offer but I fear my German is even worse than yours. I'd actually forgotten about those pages until I started writing my reply - and as I now have pretty good access to literature I should be able to find better references (although its not massively appealing, they were frustrating pages to work on). BTW if you need access to papers I'd be quite happy to dig them up for you. Project Osprey (talk) 22:30, 23 October 2014 (UTC)
thanks for that kind offer. Axiosaurus (talk) 10:02, 24 October 2014 (UTC)

DOI at Molecular gyroscope[edit]

Clicking on the doi:10.1002/1521-3773(20020118)41:2<275::AID-ANIE275>3.0.CO;2-M link takes me to http://onlinelibrary.wiley.com/resolve/doi?DOI=10.1002/1521-3773%2820020118%2941:2%253C275::AID-ANIE275%253E3.0.CO%3b2-M which says "Page Not Found ". Does it work for you? It's possible that the DOI string is given in the ref when one can find the ref, but something is wrong here. Is this a bug in the doi: URL-generation encoding? DMacks (talk) 15:21, 24 October 2014 (UTC)

For me it works fine, I'm taken to: http://onlinelibrary.wiley.com/doi/10.1002/1521-3773(20020118)41:2%3C275::AID-ANIE275%3E3.0.CO;2-M/abstract
The difference seems to be that in your case the brakets have been converted into unicode. I'm in work atm so I'm accessing via IE, what about you? Project Osprey (talk) 15:26, 24 October 2014 (UTC)
I've tried it now from home using Firefox and I'm getting the same error message as you. Project Osprey (talk) 19:25, 24 October 2014 (UTC)

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Chemistry topics[edit]

Project Osprey, I'm glad to know of our mutual interest in chemistry, and thank you for the upgrades you provided to my recently created Wikipedia article. If you have a moment, please take a look at another article I recently originated related to chemistry, on William C. Drinkard. Many thanks, Nolabob (talk) 16:51, 10 January 2015 (UTC)

Thanks for getting in touch. I don't tend to do a lot of editing at the weekends but I'll take a look of that article over the coming days and see if there's anything I can add. You could also bring it to wider attention by posting something over at WikiProject_Chemistry... Lord knows we need more active chemists there. --Project Osprey (talk) 17:06, 10 January 2015 (UTC)

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F2 complex[edit]

I havent read the Russian report on an F2 complex but it is probably ... I check later this AM when I get to work and access to the journals online. Of course F2 has lone pairs which could make it pretty different. Thanks by the way for all you are doing around here, your influence is really helpful. --Smokefoot (talk) 14:35, 16 January 2015 (UTC)

I agree that it seems unlikely - when you compare the strength of a F-F bond to a F-M bond the metal always wins, even an unreactive metal like gold. I wouldn't be surprised if this were a low-spin [AuF6]+[F]-. To be honest though I'm dealing with articles in bulk at the moment, I'm doing some PRODing and cross-linking as I go but little more than that. And thank you, it's always nice to have someone interested. --Project Osprey (talk) 15:48, 16 January 2015 (UTC)
Its a spectroscopy study on "stuff", that's what I gleaned from ChemAbs. My institution doesnt have access to that journal directly, so but dont get your hopes up. Russian journals are filled with mediocrity, unfortunately.--Smokefoot (talk) 18:22, 16 January 2015 (UTC)

Dow Corning[edit]

Hi Project Osprey, I wanted to thank you for your help with assessing Dow Corning and improving the article's references. I've proposed a few additions to the article on the talk page, here, which I'm hoping could flesh out some of the basic background information the article is currently missing. If you have a moment, I'd be really grateful if you could take a look and let me know what you think. Thank you! Mary Gaulke (talk) 15:16, 6 May 2015 (UTC)

I don't generally tend to edit pages about companies as I find it difficult to find neutral sources, but I'll give it a try over the coming days. --Project Osprey (talk) 09:16, 7 May 2015 (UTC)
Super appreciated - thanks again! Mary Gaulke (talk) 15:09, 7 May 2015 (UTC)

Betaines[edit]

Thanks for help with recent renovation of quat salts used in laundry. I figured if us chemists dont step in, articles on these household apps sound flimsy. So any advice or suggestions are welcome. Now abuot betaines.... Are you sure? Check out http://goldbook.iupac.org/B00637.html. The quat salts that Ullmann's encyclopedia point to are simple cations, not zwittreions, which is what I think betainss are. I did find (in Ullmann's) that betaines are useful in dishwashing agents, which apparently is a higher end market and allows such fancy compounds to be used. The section Dishwashing liquid#Common ingredients is a place I plan to mention them. Here is what Ullmann's has to say about betaines and laundry: "Compounds of the alkylbetaine or alkylsulfobetaine type ... Despite what could be seen in some respects as excellent detergency properties, ... are only rarely employed in laundry detergents, primarily for cost reasons. They are mainly applied in manual dishwashing products." --Smokefoot (talk) 22:22, 18 May 2015 (UTC)

I've only been working in this area for about 12 months, so I may be wrong, but the term 'betaine' does come up a lot (e.g. Cocamidopropyl betaine) with 'betaine ester' often denoting a quat with a cleavage ester linkage (increasingly popular for environmental reasons). Regarding dishwashing, alkyl betaines are often mild biocides, making them appealing for such applications. This may be an issue of an industry term not making the leap into literature - companies don't publish many papers as a rule... or I may be wrong, I don't have access to scopus atm so I can't cite any reviews as evidence - Give me till tomorrow? --Project Osprey (talk) 00:27, 19 May 2015 (UTC)
Take your time. These articles have been without chemical info for several years. I am pretty unfamiliar with the area. --Smokefoot (talk) 22:27, 19 May 2015 (UTC)

Set index articles[edit]

FYI: A set index article is not a disambiguation page, its a type of list article and follow the style guidelines at Wikipedia:Stand-alone lists. :-) Christian75 (talk) 11:44, 10 June 2015 (UTC)

Hmm... in that case we may have a problem with Category:Chemistry_set_index_pages. Many of these are functioning as disambiguation pages and have no references. I have myself encountered a problem with other editors who feel that disambiguation pages should say nothing more descriptive than "may refer to". Pages with short leads like "X refers to a class of compounds which containing both Y and Z groups. Important members include:" fall foul of this and get turned into articles; which then collect tags for being unreferenced etc (it can be very hard to find a references for such a general concept). What is the solution for this? --Project Osprey (talk) 12:21, 10 June 2015 (UTC)
I just checked some random articles i category:Set indices - same problem. In the future I will just ignore SIA without references, and "pretend" its a disabiguation page. Another problem. If we threat them as List articles, most of them would be deleted after a WP:AfD. Sorry for the interruption. Christian75 (talk) 12:53, 10 June 2015 (UTC)
No problem. (if this issue with SIA is common should we propose a change to their definition?). --Project Osprey (talk) 14:34, 10 June 2015 (UTC)

Unhelpful edit by unapproved bot?[edit]

If you're going to run a bot, you must seek to get it approved. this edit (edit summary: "ref fixes (semi-automated using reFill)") deleted useful information from the citation. If it's not a bot, please take more care.--Elvey(tc) 17:19, 16 June 2015 (UTC)

Sorry. I just use the bot, I didn't build it. It is hosted on Wikimedia Labs, so I presume it's been approved by someone. The edit appears to have improved 3 refs but damaged 1, which is not ideal. I'll try to be more careful in future. --Project Osprey (talk) 08:23, 17 June 2015 (UTC)

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Thanks for your collegiality[edit]

I dont typically sem-revert my colleagues, so I dont know what got into me this AM - not enough coffee, assertiveness hormones over-secreted, ... But in any case we're all trying to do the right thing. If you feel that my edits are bungled, you should always feel free to revert me. I will be offended for a few seconds and then fully recover. Thanks, --Smokefoot (talk) 22:25, 25 August 2015 (UTC)

It's not a problem, I don't typically un-revert my colleagues either. I can have strong opinions regarding leads but what is and isn't an encyclopedic tone is often a matter of personal precision; I'm aware that I prefer a more conversational tone than most. In any event that page seems to have attracted a lot of editing recently so both of our work is probably going to get buried under subsequent edits. --Project Osprey (talk) 23:03, 25 August 2015 (UTC)

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Not sure it matters, but in case ...[edit]

Science Barnstar Hires.png The E=mc² Barnstar
You are doing a lot of good work, and others notice. Smokefoot (talk) 02:25, 26 September 2015 (UTC)
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[edit]

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[edit]

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[edit]

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 (talkcontribs) 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[edit]

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)

A barnstar for you![edit]

Original Barnstar Hires.png The Original Barnstar
Thanks for your reply Zyvov 13:53, 21 October 2016 (UTC)

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CX717[edit]

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 (doi:10.1016/j.coph.2014.11.002) 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? doi:10.1371/journal.pbio.0030299. 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[edit]

  • 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.

Thats for now, --Smokefoot (talk) 16:24, 2 December 2016 (UTC)

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[edit]

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[edit]

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?[edit]

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)+C2R. 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[edit]

Here's the TOC from Ullmann's chapter on "Metallic Soaps"

  • 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

.... Its not my idea and I was surprised by the terminology. Your friendly stalker. --Smokefoot (talk) 13:37, 8 May 2017 (UTC)

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[edit]

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[edit]

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

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C2 ligands[edit]

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[edit]

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 doi:10.1002/bms.1200150106. 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)