Quantum chemical study of the mechanisms of the reaction of aminolysis of esters in aprotonic medium

Abstract

1. The mechanisms of the reaction of aminolysis of esters in aprotonic medium were analyzed by the CNDO/BW method. The profiles of the potential surfaces of the noncatalytic and catalytic pathways of the reaction were calculated, and an estimate was given for the values of their activation energy, which agree with the experimental data. 2. The limiting step in the reaction is intramolecular transfer of a proton from a nucleophilic reagent to a leaving group; the noncatalytic reaction practically cannot take place. Catalysis according to the mechanism of cyclic proton transfer and with the participation of a proton acceptor is the most effective.