An Improved Chiral Recognition Model for Resolving N-ACYL-α-arylalkylamines on Pirkle-Type π-Acidic Chiral Stationary Phases

An improved chiral recognition model for resolving N-acyl-α-arylalkyl-amines on Pirkle-type π-acidic chiral stationary phases (CSPs) has been proposed based on the chiral resolution trends of a homologous series of N-acyl-α-(1-naphthyl)ethylamines on CSPs derived from N-(3,5-dinitrobenzoyl)-(R)-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-α-(1-naphthyl)alkylamines on CSP 1 and 2 and a homologous series of N-acyl-α-(1-naphthyl)ethylamines and N-acetyl-α-(1-naphthyl)alkylamines on CSP 5, which has the same structure as CSP 1 except the tether direction.