Quantum-chemical study of the mechanism of the hydrolysis of amides in the gas phase and in aqueous solution

The MNDO, AM1, and MNDO/M methods have been used to calculate the profile of the potential energy surface for the hydrolysis of formamide in the gas phase and in aqueous solution. Estimates have been made of the changes in the energy barrier in specific acid and base catalysis, and it is shown that in the absence of proton exchange between the reacting system and the solvent the interaction of the charged reactants with a polar medium impedes the reaction.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 8, pp. 1785–1792, August 1989.