Investigation of the chiral recognition by “Brush‐Type” phases in liquid chromatography using crystal structure analyses of diastereomeric 1:1 complexes of a π‐donor and a π‐acceptor derivative of leucine

Abstract

Abstract (R,S)‐ N ‐Acetyl‐leucine‐2‐naphthylamide can be resolved into its enantiomers on a (S)‐DNBLeucine chiral stationary phase. The mechanism of this separation was investigated using as model complexes the 1:1 S,S‐ and the 1:1 R,S‐cocrystals of the above naphthylamide and N ‐3,5‐dinitrobenzoylleucinemethylamide, a soluble analogue of the stationary phase. The observed enantiomeric elution order can be rationalized from their X‐ray data.