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A comparative density functional theory study of tungsten-based Fischer carbenes, tungsten- and molybdenum-based Schrock carbenes, and ruthenium- and osmium-based Grubbs-type olefin metathesis catalysts reveals that the last group of catalysts should not be taken to be intermediate between the two established categories of carbenes. Rather, the Grubbs catalysts have characteristic properties similar to those of the Schrock family of carbenes and can be viewed as an extension of the latter class. Whereas an appreciable fraction of the electrons involved in the carbene bond of Fischer carbenes are unshared, and these compounds may be classified as “ionic” or “donor- acceptor” carbenes, a distinct covalent character is observed for both Schrock carbenes and Grubbs catalysts, which thus together fall into a larger category that may be termed “covalent” or “electron-sharing” carbenes. For these compounds, the energies of the atomic valence d orbitals determine the polarization of the and pi components of the carbene bond. Whereas the early metals (as reflected in valence d orbitals of relatively high energies) W and Mo render Schrock carbenes weakly nucleophilic, the later metals Ru and Os form weakly to moderately electrophilic carbenes. Schrock carbenes may thus, more accurately, be classified as “nucleophilic covalent” or “nucleophilic electron-sharing” carbenes, while Grubbs catalysts could be termed “electrophilic covalent” or “electrophilic electron-sharing” carbenes.
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Reference：
Highly efficient and robust molecular ruthenium catalysts for water oxidation,
Catalysts | Special Issue : Ruthenium Catalysts – MDPI