Quantum-chemical investigation of the mechanism of nucleophilic addition in the HCNO molecule

Calculations by the MNDO, AM1, and MNDO/M methods were undertaken for the reaction of HCNO and CH₃OH. It was shown that the MNDO and AM1 methods overestimate the activation energy of the reaction involving proton transfer, and this leads to an incorrect conclusion about the mechanism of the process. It was concluded that the reaction of the HCNO molecule with nucleophiles takes place in a single stage by a concerted asynchronous mechanism. The product in the Z configuration is formed as a result of the stereospecific reaction.Translated from Teoreticheskaya i Éksperimental'naya Khimiya, Vol. 25, No. 6, pp. 719–722, November–December, 1989.