HR-DOSY and sulfoxide enantiomeric discrimination by cyclodextrin

Abstract

Racemic and chiral ethyl-phenylsulfoxide (solute) and β-cyclodextrin (chiral selector) were used to compare two NMR methodologies to predict RP-HPLC enantiomeric resolution efficiency. One of them based on the classical approach involving apparent binding constants and complexation-induced chemical shifts at saturation and the other based on 13C NMR signal splittings (solute and chiral selector in stoichiometric ratio) and HR-DOSY of the same solution. We have concluded that the latter methodology is rather efficient and though more elaborate from the NMR point of view, the results are promising and constitute an alternative method to investigate chiral recognition and other supramolecular phenomena.