Directly probing the racemization of imidazolines by vibrational circular dichroism: kinetics and mechanism.

Abstract

The first report of monitoring the kinetics of racemization in solution by online vibrational circular dichroism (VCD), chemometrics, and density functional theory (DFT) calculations is presented. The activation energy for the racemization of an imidazoline based on the experimental VCD was determined, and the detailed mechanism of the process utilizing DFT calculations was elucidated. This study demonstrates the utility of VCD for the determination of reaction mechanisms in asymmetric transformations.

DOI: 10.1021/ol100734t