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The tris[(1-isopropylbenzimidazol-2-yl)dimethylsilyl]methyl ligand, [Tism Pr i Benz ], has been employed to form carbatrane compounds of both the main group metals and transition metals, namely [Tism Pr i Benz ]Li, [Tism Pr i Benz ]MgMe, [Tism Pr i Benz ]Cu and [Tism Pr i Benz ]NiBr. In addition to the formation of atranes, a zinc compound that exhibits κ 3 -coordination, namely [κ 3 -Tism Pr i Benz ]ZnMe, has also been obtained. Furthermore, the [Tism Pr i Benz ] ligand may undergo a thermally induced rearrangement to afford a novel tripodal tris(N-heterocyclic carbene) variant, as shown by the conversion of [Tism Pr i Benz ]Cu to [κ 4 - C  4 -Tism Pr i Benz* ]Cu. The transannular M-C bond lengths in the atrane compounds are 0.19-0.32 Å longer than the sum of the respective covalent radii, which is consistent with a bonding description that features a formally zwitterionic component. Interestingly, computational studies demonstrate that the Cu-C atrane interactions in [Tism Pr i Benz ]Cu and [κ 4 - C  4 -Tism Pr i Benz* ]Cu are characterized by an "inverted ligand field", in which the occupied antibonding orbitals are localized more on carbon than on copper.

chemical science

Tris[(1-isopropylbenzimidazol-2-yl)dimethylsilyl]methyl metal complexes, [Tism<sup>PriBenz</sup>]M: a new class of metallacarbatranes, isomerization to a tris(N-heterocyclic carbene) derivative, and evidence for an inverted ligand field

Tris[(1-isopropylbenzimidazol-2-yl)dimethylsilyl]methyl metal complexes, [TismPriBenz]M: a new class of metallacarbatranes, isomerization to a tris(N-heterocyclic carbene) derivative, and evidence for an inverted ligand field

Tris[(1-isopropylbenzimidazol-2-yl)dimethylsilyl]methyl metal complexes, [Tism^PriBenz]M: a new class of metallacarbatranes, isomerization to a tris(N-heterocyclic carbene) derivative, and evidence for an inverted ligand field