Talk:Grubbs catalyst

"Importance"

I would vote for that it was a importance=top. Grubb's won the Nobel Prize for it! ChristianB (talk) 16:56, 19 November 2007 (UTC)

Apart from that I'd say it's important in the field of N-heterocyclic carbenes because it is the one example of a commercially available NHC catalyst. --Rifleman 82 (talk) 17:02, 19 November 2007 (UTC)

I got carried away in my edit comment, I apologise for that, but I stand by my reassessment. I'm open to convincing otherwise, of course! Averages seen for such tags at Wikipedia:Version_1.0_Editorial_Team/Index indicate that Top-Class is used by most projects to indicate the top 1% or so in importance - which means the top 100 out of 10,000 articles (though only <2000 have been tagged so far). When I looked at Category:Top-importance_chemistry_articles this article looked really out of place, and as an organic chemist I'm naturally biased in its favour! I've listed below the G articles ranked top importance, and then the ones ranked high importance, and also shown "importance stats" i.e., "What links here" (WLI) and Interwikis (IW, no. of foreign languages with the page). Note that ruthenium is only ranked high importance!

• Grubbs' catalyst: WLI=20, IW=2

Top

• Gas: WLI=1230, IW=54.
• Gibbs free energy: WLI=143, IW=14
• Gold: WLI=4595 IW=96

High

• Gadolinium: WLI=143, IW=48
• Gallium: WLI=190, IW=61
• Gas laws: WLI=37, IW=9
• Gerhard Ertl: WLI=83 (mostly from a Nobel Prize template), IW=25
• Germanium: WLI=258, IW=63

(BTW, I'm studying such stats at the moment for WP:1.0, part of my interest in doing the numbers here). I would argue that if Grubbs' catalyst counts as a "must-have", a core topic for chemistry (the criterion for Top-Class), then why don't the Germans, the French, the Spanish, Italians, Japanese, etc have an article on this topic? Walkerma (talk) 05:40, 20 November 2007 (UTC)

I agree with Walkerma's assessment, and I think one could even make a case for "mid-importance". The Top-class contains very general articles or articles with a very wide appeal. This one is quite specialized, as we can see by how Rifleman describes it: "important in the field of N-heterocyclic carbenes". Look at it from a distance. Heterocyclic chemistry is a sort of "specialty" within chemistry. N-heterocycles are a subset of it. And N-heterocyclic carbenes are even more specific. Not everything that wins a Nobel Prize needs to be Top-importance in our assessment scheme, and in fact I would say it is quite the opposite for recent prizes. It is usually only after many decades that a prize-winning discovery becomes "Top importance", if at all. --Itub (talk) 07:50, 20 November 2007 (UTC)

Fair enough, I agree with your points (Walkerma & itub). I also agree with Itub that "mid" is probably more appropriate. Perhaps we should use some sort of metrics to classify articles? Or at least, like in this case, to check the importance rating. --Rifleman 82 (talk) 11:48, 20 November 2007 (UTC)

Regarding metrics, the hope (I'm now wearing my WP1.0 hat) is that chemists will simply judge what seems right for importance of chemistry articles, and in cases where there is disagreement a consensus will be reached. That introduces an important human element into the calculation - I'm a great believer in that. But overall importance at WP1.0 will be judged using various metrics - take a look at this brand new list showing exactly that. It's at an early stage, but I have high hopes! The idea is that anything with an additive score (which also includes a quality assessment score) of 1000 or greater would automatically go onto our next release. Feedback is very welcome here. Walkerma (talk) 06:13, 21 November 2007 (UTC)

Range of catalysts

For info, Grubbs 2 is a range of cpds- the one listed here is probably the first but there are others, e.g. [this] for those that have access to Tet. Lett. (and there is at least one other from memory). Perhaps a comment is needed to indicate that the 2nd Gen is a range? The third gen is around too, an example of its use is JACS 2007, 129, 1105-1112. Freestyle-69 (talk) 07:08, 25 September 2008 (UTC)

Hoveyda-Grubbs catalysts

I suggest that the section on the Hoveyda-Grubbs catalyst be trimmed down a bit. The examples using the water soluble catalyst are a bit specific, and there are a variety of simpler methods to do olefin metathesis in water (see http://onlinelibrary.wiley.com/doi/10.1002/anie.200801451/pdf). The image file "Grubbswatersolublecat.png" could easily be removed, which would condense the section down nicely. This would also clarify the synthesis of this type of compound, while they can be synthesized from the 1st generation Hoveyda-Grubbs complex they are generally synthesized from the corresponding 2nd generation Grubbs catalyst. Vdubbs 22:03, 4 May 2012 (UTC) — Preceding unsigned comment added by Vdubbs (talk • contribs)

Sensitivity of 2nd gen?

Where does the information the second generation would be stable towards air come from? I don't know what it is, but sigma-aldrich states otherwise.

References

interactive image is just iron flat/2D

The interactive JSmol image (property box/identifiers) only displays flat 2D wire model. I would welcome if the model instead were 3D and ball-and-stick similar to the one the static image in the property box depicts. Pythonik (talk) 15:54, 16 January 2024 (UTC)

The JSmol link looks nicely 3D-ball&stick to me, though the initial perspective is unusual. Did you try rotating it? DMacks (talk) 17:21, 16 January 2024 (UTC)

Interesting, by today's visit [2024-01-17 Wed], it is 3D-ball&stick (same browser, no OS upgrade). I remember that I opened the console of JSmol and run a couple of times the `minimize;` command to obtain a (somewhat) reasonable 3D model. Not sure if this launched some changes here on Wikipedia, or at St. Olaf (as home of Jmol/JSmol). For the purpose to inspect the complex from multiple directions, interactively, surely "good enough".

There still is an other observation about imidazolidine in the Grubbs catalyst (second generation) which still makes me wondering a bit. For one, N-C(Ru)-N, these four atoms are i) all in one plane, ii) the angle N-C-N as well as N-C-Ru, and iii) the absence of hydrogen on C surrounded by the imidazolidine nitrogen and ruthenium let me think the depiction might be better with a C=Ru double bond to the NHC carbene in addition to the already depicted Ru=C double bond engaging with the benzylidene ligand. See https://commonchemistry.cas.org/detail?cas_rn=246047-72-3 for how ACS depicts this as flat 2D scheme, as well as the .mol file (when read in Jmol, File -> Console and a couple of times a `minimize;` as 100 cycles UFF optimization are not enough.

An additional reasoning is the figure "Synthesis of the second–generation Grubbs catalyst" with a precursor with explicit H and OMe bound to said carbon, neither one the interactive JSmol interactive image retain. Else, I do not obtain the Hill formula of C46H65Cl2N2PRu mentioned by the property box (or ACS'/CAS Common Chemistry), but C46H66Cl2N2PRu (for one H [still] present i.e. N-C(Ru)(H)-N). As this compound in question is equally commercialized as "Grubbs Catalyst^® M204", I observe conflicting representations. Sigma with "a single bond" (see https://www.sigmaaldrich.com/US/en/product/aldrich/569747), ChemBeads with a "double bond" (see https://www.sigmaaldrich.com/US/en/product/sial/919764). Pythonik (talk) 18:09, 17 January 2024 (UTC)