AbstractEnantiomeric amide derivatives of (S)‐ and (R)‐1‐phenyl‐2‐aminopropane (dextro‐ and levoamphetamine, respectively) were resolved by high performance liquid chromatography on commercially available ionically and covalently bonded chiral stationary phases ((R)‐N‐(3,5‐dinitrobenzoyl)phenylglycine). Ten enantiomeric amide pairs were synthesized and chromatographed on the columns by using a mobile phase of hexane‐isopropanol (97 : 3), a flow rate of 2 ml/min, and a column temperature of 20°C. The (R)‐isomer of all 10 amides eluted first on the covalent column as did the (R)‐isomer of nine derivatives on the ionic column. however, the 3,5‐dinitrobenzoyl amide of (S)‐ amphetamine eluted before the (R)‐isomer on the ionic column. This reversal in enantiomeric elution order reveals the complexity of the interactions occurring on these columns and emphasizes the hazards of relying on observed elution order as ana prioriindica