A DFT Study on the Cycloaddition of Dimethyl Acetylenedicarboxylate and 3,4-dihydroisoquinoline-N-oxide

Abstract

A theoretical study of the kinetics and mechanism of the second-order intermolecular cycloaddition of dimethyl acetylenedicarboxylate and [3,4-dihydroiso-quinoline-N-oxide] was performed using DFT methods at B3LYP levels of theory with a 6-311G (d,p) basis set at 298.15 K. Equilibrium molecular geometries and harmonic vibrational frequencies of the reactants, transition state and product were calculated. The effect of solvent on the kinetic and thermodynamic parameters of the reaction were investigated. The calculated rate constants and activation parameters showed good agreement with experimental results. These calculations indicated that the reaction proceeds through a synchronous concerted mechanism.