A theoretical investigation of the isomers of diazomethane (CH2N2). I. Geometry, bonding, and chemical reactivity

Abstract

A searching theoretical investigation has been carried out on the five structural isomers of diazomethane, CH2N2; the isomers are diazomethane, cyanamide, isocyanamide, nitrilimine, and carbodiimide. The non- empirically calculated structures for the latter three compounds are the first to be reported. ��� Use has been made of localized exclusive orbitals to help explain the bonding and electronic structure in this series of molecules. ��� In addition, interesting use has been made of electrostatic potential maps in assessing positions of high nucleophilicity in each isomer. This information has allowed mechanistic pathways to be postulated for the protonation of diazomethane and cyanamide and for the production of isocyanamide from diazomethane.