Reactivity and mechanism of nucleophilic addition reaction of amine with alkene: A systematic DFT study

Abstract

The reactivity and mechanism of the nucleophilic addition reaction of diethylamine 1 and 1-cyano-2-phenyl vinyl methane sulfonate 2 have been studied for a systematic understanding of this relevant organic transformation, using DFT calculations method at the B3LYP/6-311G(d,p) computational levels. Analysis of the conceptual DFT reactivity indices allows explaining the reactivity, and the calculated nucleophilic and electrophilic Parr functions at the reactive sites of reagents 1 and 2, respectively, allows explaining correctly the regioselectivity observed experimentally. The study has also been applied to predict the mechanism of the amine with an alkene. Interestingly, the study predicts a switch to a two-step mechanism due to the higher polar character of this zw-type nucleophilic addition reaction.