Quantum chemical study of the influence of electronic factors on the thermodynamic characteristics of 1,3-dipolar cycloaddition of benzonitrile oxides and benzonitrile sulfides to weakly activated alkenes

Abstract

The main thermodynamic characteristics of the reactions of para-substituted benzonitrile oxides and benzonitrile sulfides with propylene were calculated by the density functional theory (DFT) method with the B3LYP hybrid functional and 6-31G(d) split-valence basis set using the Gaussian 09 program package. In all cases, introduction of the electron-withdrawing nitro group into the dipole molecule promotes the cycloaddition reaction.