The effect of the reagents nature on nucleophilic addition of acetylenes to the C=N bond of aldimines: a quantum-chemical investigation

Abstract

Abstract A quantum-chemical simulation of the mechanism of ethynylation of aldimines with substituted acetylenes was carried out. Kinetic and thermodynamic characteristics of this reaction for various reacting pairs were estimated by the B2PLYPD/6-311+G**//B3LYP/6-31+G * method. It was shown that in the reaction with N-alkylaldimines, the ethynylation barrier was significantly higher than in the reaction with N-arylaldimines. The change in the substituents at acetylene has no effect on the ethynylation barriers.