Quantitative correlation between calculated molecular properties and retention of a series of structurally related racemates on cellulose triacetate

Abstract

Racemic compounds consisting of an alicyclic six-membered ring with a phenyl group attached to the chiral carbon atom have been investigated. The chemical structure of the alicyclic part was varied systematically, in order to establish its influence on the separability of the racemates into their pure enantiomers on cellulose triacetate (CTA). Theoretical investigations, involving conformational analysis and charge distribution, have been undertaken to correlate structural features with chromatographic behaviour. For this class of compounds two major parameters governing the interaction with CTA are the rotational freedom of the bond to the phenyl group and thereby the relative ability to assume the flattest possible conformation, and a negatively charged neighbourhood of the chiral centre.