Talk:Organometallic chemistry

Wiki Education Foundation-supported course assignment
This article is or was the subject of a Wiki Education Foundation-supported course assignment. Further details are available on the course page. Student editor(s): Mastrofran. Peer reviewers: Mpizzuto15.

Above undated message substituted from Template:Dashboard.wikiedu.org assignment by PrimeBOT (talk) 05:50, 17 January 2022 (UTC)

Untitled
Should Grubbs and Schrock be listed here?
 * Yes, definitely! Walkerma 03:41, 14 May 2006 (UTC)

Should it be merged to organometallic chemistry? And what of the subject's duplicates?
 * I expanded it, with the informations I added, I believe it can be placed under organometallic chemistry.. Also there are stub duplicates like Organometallic Compound(without s), or organolithium compunds. Should they be deleted? Or how do we redirect from those pages?

23:36, 10 September 2006 (UTC) iSina
 * You must be new here. This is the talk page for the article Organometallic chemistry, which it appears you have never edited. You probably wanted Talk:Organometallic compounds, the talk page for the article Organometallic compounds. For redirects and merging, please read Redirect and Merging and moving pages. I'll try to fix the organometallic situation later today, so if you can't figure it out, don't worry about it. Feel free to ask questions on my user talk page, User talk:Keenan Pepper. —Keenan Pepper 12:56, 11 September 2006 (UTC)


 * just one editor in favor of merge but it simply takes too long to get more replies: both contents were overlapping, therefore merge completed. V8rik 21:18, 18 December 2006 (UTC)

mercurichrrome
what happened to mercurichrome? —The preceding unsigned comment was added by CorvetteZ51 (talk • contribs).


 * You mean mercurochrome? DMacks 18:04, 30 May 2007 (UTC)

Definition
"Organometallic chemistry is the study of chemical compounds containing bonds between carbon and a metal.[1]" This quote from Crabtree is taken out of context and is misleading. Most TM organometallic compounds do not contain C-M bonds. Hemoglobin, for example, has no Fe-C bonds, but noone would argue that it is not organometallic, and would be encompassed in the field of study known as organometallic chemistry. Thus the opening statement is wrong, even though the chemistry (chemistry is the reaction in this case and not a field of study) of these organometallic compounds does usually lead to a C-M intermediate at some point - but not always. A better def IMO would be that organometallic chemistry is the study of the interaction or the reaction of organic compounds and metals. Stating the obvious, but not open to misinterpretation. Endtothemeans (talk) 05:49, 7 June 2008 (UTC)


 * You are confusing organometallic chemistry with coordination chemistry. --07:03, 7 June 2008 (UTC)


 * Transition metals have a coordination sphere, and TMs can form organometalic compounds, when that coordination sphere contains organic compounds. TMs can also undergo organometallic reactions when they react with organic molecules (such as oxypalladation of an olefin). My main point here, however, is that organometallic compounds described in the article do not fit the definition on the page. The article even uses Hemoglobin as an examples.  Major revisions are necessary and there is alot of room for expansion, but the first sentence (definition) must be changed first.  I will work on expanding this article and finding better citations. Endtothemeans (talk) 13:24, 7 June 2008 (UTC)


 * You raise two points, (1) a (fundamentalist?) view of the field of organometallic chem. and (2) the need for improving the article. Regarding #1, as Itub mentions, the difference between coordination chemistry and organometallics can be a little blurry but organometallic chemists do not consider myoglobin as organometallic nor do we consider acetylacetonates, even though a decent organometallic chemist knows a lot about these species. In my more fundamentalist moods, I dont even consider iron carbonyl to be organometallic because it contains no organic ligands.  We held a similar argument about whether carbon tet is organic or not.  But most practitioners accept the definition that there is a M-C bond and iron carbonyl is widely used to make things with C-H bonds.  HbCO might be considered organometallic.  This kind of definition game has been played out a zillion times - metal cyanides, metal hydrides, ... These debates have not proven very productive, and meanwhile the articles need content!  Regarding your second point, indeed most of the chemistry articles merit attention and it seems that you have some ideas.  In general, however, I recommend focusing your editing energies on contributing and explaining facts and principles rather than fussing over strict definitions.  Readers are looking for information, not definitions.--Smokefoot (talk) 13:45, 7 June 2008 (UTC)


 * Point taken, but the content needs to be accurate (most chemistry related articles are appauling). I cannot expand on an article if I dont agree with what we are talking about.  The bottom line is that the information in this article contradicts itself.  Also, I never considered metalcarbonyls to be organometallic compounds, although they certainly can be used to effect organometallic chemistry, as can a multitude of other inorganic compounds.  This is another reason why the definition is a very poor one, as it does, as you say, contain a M-C bond, but no organic ligand. How can something that contains a metal (inorganic) and carbon monoxide (inorganic) be organometallic?  I will let sleeping dogs lie though Endtothemeans (talk) 14:24, 7 June 2008 (UTC)
 * It is interesting to note the number of critics that comment on the "appalling" state of these articles, but these same critics lack either the required knowledge or the public spirit to address these deficiencies in Wikipedia. The bottom line being that they let sleeping dogs lie and other cliches.--Smokefoot (talk) 14:57, 7 June 2008 (UTC)


 * Endtothemeans is definitely confusing organometallics with coordination chemistry, a mistake often made by even some professionals. A compound that contains both metal and carbon may either be a metal salt, coordination compound or a true organometallic compound with a carbon-metal bond. Of course there must be fuzzy areas like with metallocenes and coordinated 1,5-cyclooctadiene, but that is to be expected. The main difference is that organometallic/organometallic coordination chemistry encompasses the chemistry of the interaction between carbon and metal, whereas salts and heteroatom-coordinated compounds (such as hemoglobin) involve the chemistry of metal interacting with a heteroatom, such as oxygen or nitrogen. The latter chemistry is related more to the chemistry of the heteroatom in question than organometallics per se. --Vuo (talk) 17:29, 7 June 2008 (UTC)


 * A large portion of organometallic chemistry deals with coordination complexes - they are not exclusive. Endtothemeans (talk) 00:59, 8 June 2008 (UTC)


 * I think the problem is that the boundaries of field itself are fuzzy, so naturally any attempt to come up with a "perfect" definition is bound to fail. Every organometallic chemist will agree that Ferric chloride is not an organometallic compound but that ferrocene is, but not everyone would agree where to put iron pentacarbonyl. Likewise, the chemistry of M-Si bonds is very similar to that of M-C bonds, and these types of cmpds are generally studied by folks who call themselves organometallic chemists, but trisTMSsilyl lithium will never fit any definition of organometallics that rests on the presence of an M-C bond. In short, I think the current lead is great. Yilloslime (t) 01:40, 8 June 2008 (UTC)
 * This dispute bears resemblance with the dispute over the exact definition of organic chemistry. Actually, the current lead of the aforementioned article is somewhat missing the point and should be rewritten. Organic chemistry is like pornography, I know it when I see it. Trying to come up with an exact definition inevitably leads to essentialist arguments. --Vuo (talk) 07:27, 8 June 2008 (UTC)

Organic coordination compounds - unknown lexicon?
I replaced the term "organic coordination cmpd." I have never ever heard this term, so it is at best obscure (no doubt the term has been used, every permutation of such words have). WE is probably not the ideal place to promote the use new terms; that might be considered to be a form of original research. One can sense what other editors are striving for with this section, but more conventional names might be preferable. If I am incorrect with my views, please accept my apologies. Others that have also published and taught in organometallics, should comment.--Smokefoot (talk) 17:41, 18 June 2008 (UTC)
 * I agree that "organic coordination cmpd" is at best obscure and should be avoided. Yilloslime (t) 17:44, 18 June 2008 (UTC)
 * Along similar lines, I don't recall ever seeing or using the term "organo-inorganics." Is this a term used in is some regions or subfields but not others (in which case, we should probably keep it), or a little used neologism (in which case we should probably get rid of it? Yilloslime (t) 18:13, 18 June 2008 (UTC)
 * Sorry for not getting the liturgy right the first time. The common term is metalorganic complex. --Vuo (talk) 16:28, 24 June 2008 (UTC)

Red links in Organometallics section
In the section Organometallic_chemistry, there are several redlinks. At first I thought the there was link for every element in each period. i.e. organosodium, organomagnesium, organoaluminum, etc., but upon closer inspection there isn't. The section seems rather arbitrary. For consistency's sake I think we should either eliminate all redlinks, or include all elements. As the section currently stands, I can't figure out why, for example, there is a redlink to organocobalt but not to organovanadium. Yilloslime (t) 18:21, 18 June 2008 (UTC)

Distinguished from what?
In the first sentence of the organometallic compound section, it says that organometallic compounds are distinguished by the organo- prefix. But what type of compounds are they distinguished from by use of this prefix? I'm not an expert in organometallic chemistry so I'll leave this to be answered by someone more qualified, but I thought I'd point out that this statement seems a bit incomplete. --Giftiger wunsch (talk) 17:55, 16 April 2010 (UTC)


 * the answer to your question is given in the lead ; containing bonds between carbon and a metal, meaning as opposed to compounds containing a metal but not a carbon to metal bond V8rik (talk) 19:38, 16 April 2010 (UTC)
 * Ah; fair enough. --Giftiger wunsch (talk) 20:26, 16 April 2010 (UTC)

containing bonds between carbon and a metal
Surely there is more to it than that. I'm not a chemist but to me that includes simple carbides.. 132.3.33.68 (talk) 18:01, 22 August 2011 (UTC)

Request regarding sourcing—a moratorium to certain types of edits suggested
I came here today to wikilink a new article to this one, and I simply cannot as it stands, for the article's current structural, scope, and content issues. It needs expert inorganic and organometallic attention, as it does not begin to capture, in summary, the content of Crabtree, Elschenbroich, etc.

Because of the needs of the article, and the current content status, I would like to ask that there be a moratorium to addition of any further text, without complete citations added in the same editing session. While this article clearly has some knowledgable contributors, the article is not being served by the pattern in place, that people can make substantial edits (add sentences with chemistry content) off of the top of their heads, without (i) deriving it from a clear source, and (ii) stating that source. If the best of the editors here (professional chemists, many) do so, there will not necessarily be a decay in content. But if that pattern is followed by other editors, less knowledgable and experienced, then the inevitable course of the article is decay.

Can we agree, no more substance added to the article, except from good secondary sources? I have added two of the texts used in many graduate organometallics courses to a Further reading section, as a starting point for an appreciation of the proper scope (coverage) that this article will have, when it becomes a GA.

Cheers. Le Prof Leprof 7272 (talk) 14:54, 23 May 2016 (UTC)
 * It's uneven. These articles on big topics are the most difficult to write, but then again who reads them in any detail? People completely unfamiliar with the field would at least get an impression of organometallic chemistry by glancing at this article. A rational way to repair the article would be to allocate space proportional to importance or scale, but the former is semi-subjective and I dont know where to get info on the latter.  Another way to fix the article is to create a gallery, which I will start now.  You and others are welcome to replace or add.--Smokefoot (talk) 02:53, 24 May 2016 (UTC)

Citation with markup issue
The following citation appears with a bold text insertion—an apparent link, "Organometallic chemistry"—that I cannot find in and so remove from the markup. The text is placed here, so another can find and remove this unwanted final text material. If this problem is solved, the source can be re-added after the first sentence of the "Environmental…" section.

Cheers. Le Prof Leprof 7272 (talk) 14:54, 23 May 2016 (UTC)

External links modified
Hello fellow Wikipedians,

I have just modified 1 one external link on Organometallic chemistry. Please take a moment to review my edit. If you have any questions, or need the bot to ignore the links, or the page altogether, please visit this simple FaQ for additional information. I made the following changes:
 * Added archive http://web.archive.org/web/20060625174426/http://ocw.mit.edu:80/OcwWeb/Chemistry/5-44Fall-2004/CourseHome/index.htm to http://ocw.mit.edu/OcwWeb/Chemistry/5-44Fall-2004/CourseHome/index.htm

When you have finished reviewing my changes, please set the checked parameter below to true or failed to let others know (documentation at ).

Cheers.—cyberbot II  Talk to my owner :Online 12:12, 25 May 2016 (UTC)

Proposed Edits
The Organometallic Chemistry wikipedia article could be improved by expanding the content in its sections, such as 'History,' as well as adding relevant topics such as catalysis. The history section could be improved by talking about the discovery of η2 organometallic complexes (Zeise's salt). In addition, there could be more about how top-tier organometallic chemists such as Grubbs, Schrock, Crabtree, Buchwald, Hartwig, etc have expanded the field to greater heights, exploiting organometallic properties for applications such as catalysis, OLED developments, other optoelectronic materials. There also should be a section about coupling reactions, and their implications for the development of novel ligands and organic frameworks. I could also talk about chemo, stereo, and regioselectivity of organometallic compounds and their benefit in organic and inorganic chemistry.

Potential References to be used:

1. Miessler & Tarr, Inorganic Chemistry 2. Organometallic hypertextbook 3. Organometallic Chemistry - LibreText 4. Solomons & Graham, Organic Chemistry — Preceding unsigned comment added by Mastrofran (talk • contribs) 18:31, 28 November 2017 (UTC)
 * Here are some commments on your proposal. First of all, great that you communicate plans.  And even greater that you plan actual work.  Wikipedia need help.  Some specifics:

--Smokefoot (talk) 19:27, 28 November 2017 (UTC)
 * "The history section could be improved by ... top-tier organometallic chemists such as Grubbs, Schrock, Crabtree, Buchwald, Hartwig, etc" You risk sounding parochial! Its an international sport, and you are revealing a narrow worldview. Visit Japan, Germany, or UK if you want a different perspective on who is "top tier". But the gist of your argument is spot-on: we need to emphasize top-tier developments.
 * In general it is a good idea to avoid highlighting people in Wikipedia. That style can lead to cultish behavior and all sorts of conflicts of interest.  Stick to science.
 * "applications such as catalysis, OLED developments, other optoelectronic materials." Papers on these areas are often (usually) loaded with hype.  Be careful to separate the overused terms "useful" and "many applications" that fill journals but are usually baloney.  A few Ir complexes are used in OLEDs.  Otherwise caution is recommended before drinking to kool-aide.  If you want to write about applications, rely on books or encyclopedias NOT by academics.  You will discover, for example, that 99.9...% of olefin metathesis is heterogeneous using pre-Schrock/Grubbs, etc.
 * If you really want to help, you might start on Buchwald-Hartwig amination. That article needs help from someone of your level.
 * "novel ligands" is a very subjective topic. I recommend avoiding it.
 * "organic frameworks" the article is really about M-C bonds, and MOFs rarely have such, and no useful MOF has any.
 * "I could also talk about chemo, stereo, and regioselectivity of organometallic compounds and their benefit in organic and inorganic chemistry." Wonderful offer and desperate need. Please look at some of the individual articles.  Long articles tend to be less useful to readers, so expanding Organometallic chemistry might not be worth your efforts.
 * Final advice: follow WP:SECONDARY and WP:TERTIARY. Your inclination to follow the above-mentioned textbooks is a great start.  Good luck.

Added Subheadings
Hello Wiki organometallic chemistry community!

I have updated the organometallic chemistry page and including two new subheadings. The first is a brief overview of organometallic catalysis. I attempted to touch on cross-coupling and asymmetric catalysis. In addition,I have started an organometallic reactions subheading, briefly touching on very important organometallic reactions that were not previously discussed, such as sigma-bond and olefin metathesis. Mastrofran (talk) 19:48, 26 December 2017 (UTC)mastrofran — Preceding unsigned comment added by Mastrofran (talk • contribs) 18:50, 26 December 2017 (UTC)
 * comments, since you are learning organometallics, here are some perspectives to ponder:

--Smokefoot (talk) 22:06, 26 December 2017 (UTC)
 * If one wants to emphasize important "organometallic catalysis", why not start with multi-ton stuff?
 * why the emphasis on sigma-bond metathesis? It is used where?
 * "especially in cross-coupling reactions" [you mention cross coupling often): process used mainly in pharma, not in the same league with the big boy organometallic processes.
 * "Suzuki-Miyaura coupling reaction": ditto
 * "carbon-metal frameworks" (I guess MOFs): not used by anyone, anywhere, ever (yet).
 * "These strong-field carbon ligands" which strong field ligands?
 * "ample electron density for the metal catalyst to participate in redox chemistry..." wha? The situation is that some electron deficient species are good for some reactions, and some electron-rich things are good for others. Its a very, very complicated situation.
 * comments, here are some rebuttal arguments for you to consider:

Mastrofran (talk) 19:28, 28 December 2017 (UTC)mastrofran
 * Who says that I need to start with multi-ton stuff? Why is that supposed to receive greater importance?
 * Sigma bond metathesis is used for a variety of processes. It is a classic and very important organometallic reaction and is definitely something that deserves attention on the Organometallic Chemistry Wiki page.
 * Your third point is completely opinionated and irrelevant. What do you mean that cross-coupling is not in the same league as the "big boy organometallic processes?" I beg to differ. Cross-coupling has opened up many avenues for the formation and of new organic molecules, and have expanded the realm of organometallic chemistry greatly. It is used in pharma, synthesis of chemical feedstock, and herbicide/pesticide synthesis.
 * Thanks for the opportunity to comment. I figured you dont want it, but even assholes or trolls can offer advice that is useful.  When it comes to discussing what is important in a big area, one almost must rely on tertiary sources.  Its a lesson that took me a while to learn also. The impediments you face are (1) you dont know that much and (2) reviews are too narrow.  So if I want to list the top reactions in catalysis, I get books on catalysis and take a look at the chapter headings.  That is what I did in my insertion into your section: I got Piet van Leeuwen's book on Homogeneous Catalysis and basically listed chapters.  These are the big boys: hydrogenation, polymerization, acetic acid syn., hydroformylation.  Yes, cross coupling is one of them, but only one.
 * The thing we are up against in writing this section is how do we define "important". You and I can rant at each other or we can go for measureables, like scale (or $, or lives saved).  Its advice that you might consider.  Many might think that products made on the, say, 500,000,000 kilogram/y scale (polyethylene) merit mention high on a list.
 * Re: Sigma bond metathesis. It is a nifty reaction, but try to name one industrial processes that uses it, much less a major process? I dont know of any. But show me that I am wrong, that is the debate that we have on these Talk pages.  There is nothing wrong with being enamored with your new knowledge of sigma bond metathesis, but I am trying to inject some perspective.  Similarly with MOF's: fascinating and burgeoning research area, but beware of hype and try to identify who is actually using them.  --Smokefoot (talk) 20:03, 28 December 2017 (UTC)

Move important organometallic reactions to "Organometallic reactions" section?
The section "Concepts and techniques" contains a list of many fundamental organometallic reactions. Wouldn't this be better suited in the "Organometallic reactions" section? The whole organometallic reactions section could probably be rewritten. It currently does not mention transmetalation or reductive elimination which are both pretty important in catalysis and organometallic synthesis. Davination (talk) 07:12, 25 December 2020 (UTC)
 * I went ahead and moved the list of reactions to the organometallic reactions section. I do believe it fits there much better. Davination (talk) 00:24, 30 December 2020 (UTC)
 * You seem to know what you are doing. To be provocative, I guess one could question if "organometallic reaction" is a useful term or theme. Oxidative addn and transmetlation etc, one doesnt need carbon-based ligands to do those transformations. You will find that lists can be problematic in Wikipedia. Just sayin'.  --Smokefoot (talk) 00:41, 30 December 2020 (UTC)
 * I think a section dedicated to representative organometallic reactions could be useful, especially the reactions that are relevant to most catalytic cycles. You make a good point about some of these reactions not being exclusive to carbon-based ligands, perhaps the section could be renamed to better reflect that these are not only organometallic reactions. I think I understand what you mean about lists, they always seem to contain either too much or not enough depending on who you ask. If you ask me, the list is about twice as long as it needs to be and all the entries below electron transfer could go. A good amount of organometallic mechanisms can be fully described with those first six entries: associative/dissociative substitution, O.A./R.E., migratory insertion/β-hydride elimination, transmetalation, and electron transfer.


 * If lists are to be avoided, I would be happy to take a crack at turning this section into a couple short paragraphs. I feel the section currently gives too much attention to sigma-bond metathesis (which in my opinion isn't that important). Davination (talk) 06:39, 31 December 2020 (UTC)

Added information on hapticity
Hello Wiki community!

Hapticity is an important part of organometallic chemistry that was not previously included in the article. I included some information on this under the concepts and techniques section. Let me know if this is okay and if there should be anything removed/added. Ecaldero (talk) 14:18, 15 March 2022 (UTC)

Steel
Steel is organometallic. 24.176.214.250 (talk) 05:27, 24 March 2023 (UTC)