A new chiral stationary phase (CSP) for the liquid chromatographic resolution of enantiomers was prepared from (S)-naproxen and 3,5-dinitroaniline. The 6-alkoxy-2-naphthyl group of the CSP was presumed to act as a ${pi}$-basic interaction site for resolving ${pi}$-acidic racemates while the 3,5-dinitroanilide group of the CSP was presumed to play a role as a ${pi}$-acidic interaction site for resolving ${pi}$-basic racemates. From the chromatographic resolution trends of N-alkylamide derivatives of ${alpha}$-arylalkylamines on the CSP prepared, the chiral recognition mode involving the intercalation of the amide alkyl chain of the less retained enantiomers between the connecting tethers of the CSP was proposed.