Computational chemical analysis of chiral recognition in liquid chromatography, selectivity of N-(R)-1-(α-naphthyl)ethylamino carbonyl-(R or S)-valine and N-(S)-1-(α-naphthyl)ethylamino carbonyl-(R or S)-valine bonded aminopropyl silica gels

The chiral recognition of N-(R)-1-(α-naphthyl)ethylamino carbonyl-(R or S)-valine and N-(S)-1-(α-naphthyl)ethylamino carbonyl-(R or S)-valine bonded aminopropyl silica gels in liquid chromatography was examined using computational chemical analysis. The chiral recognition centers of the model chiral molecules were analyzed using the Extended Hückel CACheTM program, and then the structures of hydrogen bond complexes with analytes were optimized by molecular mechanics calculations. The differences in final energy values indicated the elution order and enantiomer separation. The optimized density of chiral phases indicated that larger sized analytes may not slip into chiral recognition brush and form a one-to-one complex with the chiral recognition molecule used for analysis.