A Computational Analysis of the Hydroacylation of Aldimines in the Presence of a Wilkinson's Catalyst

Abstract

A computational mechanistic study was performed to elucidate a feasible minimum energy pathway of a multistep hydroacylation reaction in which an aldimine combines with styrene in the presence of Wilkinson’s catalyst to form a ketimine. Molecule building software was used to construct the reactant, product, and possible intermediates along this pathway, while the molecular geometries of each were optimized by minimizing the energies with respect to the nuclear coordinates. Approximate reaction pathways were fashioned between each pair of adjacent intermediates through simple interpolation, after which sophisticated Nudged Elastic Band and Modified Dimer calculations were performed to locate the transition states for each of the multiple steps along the reaction pathway. This computational analysis generated an overall mechanistic pathway that was consistent with known experimental data. Two distinct quantum chemical software packages, DMol3 and Gaussian 09, were used to generate two separate and full reaction pathways. While no significant difference appeared between the two, the comparison provided a measure of veracity to validate the proposed reaction mechanism which resulted.