AN IMPROVED CHIRAL RECOGNITION MODEL FOR RESOLVING N-ACYL-ALPHA-ARYL-ALKYLAMINES ON PIRKLE-TYPE PI-ACIDIC CHIRAL STATIONARY PHASES

An improved chiral recognition model for resolving N-acyl-alpha-arylalkylamines on Pirkle-type pi-acidic chiral stationary phases (CSPs) has been proposed based on the chiral resolution trends of a homologous series of N-acyl-alpha-(l-naphthyl)ethylamines on CSPs derived from N-(3,5-dinitrobenzoyl)-(S)-phenylglycine (CSP 1) and N-(3,5-dinitrobenzoyl)-(S)-leucine (CSP 2). The chiral recognition model proposed has been evidenced by its successful application to the explanation of the chromatographic resolution trends of a homologous series of N-acetyl-alpha-(1-naphthyl)alkylamines on CSP 1 and 2 and a homologous series of N-acyl-alpha-(l-naphthyl)ethylamines and N-acetyl-alpha-(1-naphthyl)alkylamines on CSP 5, which has the same structure as CSP 1 except the tether direction.