The electronic structure of nitrilimines revisited

Abstract

A combination of density-functional theory and natural resonance theory has been used to show that a complete description of the electronic structure of nitrilimines, R¹CNNR², requires four resonance structures (propargylic, allenic, 1,3-dipolar and carbenic); appropriate substituents were shown to enhance the carbene character of nitrilimines to the point where they may be considered stable carbenes.