Data-Driven Prediction of Circular Dichroism-Based Calibration Curves for the Rapid Screening of Chiral Primary Amine Enantiomeric Excess Values
James R. Howard, Arya Bhakare, Zara Akhtar, Christian Wolf, Eric V. Anslyn
Abstract
Here, we describe the prediction of the circular dichroism (CD) response of a three-component chiroptical sensor for enantiomeric excess (ee) determination of chiral amines using a multivariate fit to electronic and steric parameters. These computationally derived parameters can be computed for nearly any amine and correlate well with the CD response of the 12 amines comprising the training set. The resulting model was used to accurately predict the CD response of a test set of chiral amines. Theoretical calibration curves were then created and used to determine the ee of solutions of unknown ee. Using this method, the error in ee determination differed by less than 10% compared to experimentally generated calibration curves.