Abstract
Mesoionic imidazolylidenes are recognized as excellent electron‐donating ligands in organometallic and main group chemistry. However, these carbene ligands typically show poor π‐accepting properties. A computational analysis of 71 mesoionic imidazolylidenes that bear different aryl or heteroaryl substituents in C2 position was performed. The study has revealed that a diphenyltriazinyl (Dpt) substituent renders the corresponding carbene particularly π‐acidic. The computational results could be corroborated experimentally. A mesoionic imidazolylidene with a Dpt substituent was found to be a better σ‐donor and a better π‐acceptor compared to an Arduengo‐type N‐heterocyclic carbene. To demonstrate the utility of the new carbene, the ligand was used to stabilize a low‐valent paramagnetic tin compound.
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