Mechanistic study of enantiomeric recognition of primary amino compounds using an achiral crown ether with cyclodextrin by capillary electrophoresis and nuclear magnetic resonance

A model and theoretical equations are presented to investigate the enantiomeric recognition mechanism of primary amino compounds using an achiral crown ether with cyclodextrin by capillary electrophoresis (CE) and nuclear magnetic resonance (NMR). Association constants were calculated from CE and 1H NMR experiment results on the basis of the model and the equations. The key step of chiral recognition was identified from those values. Using CE analyses of three primary amino compounds [1-(1-naphthyl)ethylamine; 1-aminoindan; 1,2,3,4-tetrahydro-1-naphthylamine], the key step was identified with the equilibrium where the complex of a primary amino compound and 18-crown-6 becomes associated with 2,6-di-O-methyl-β-cyclodextrin for all the three compounds. From the 1H NMR analyses of 1-(1-naphthyl)ethylamine, the key step was identified with the equilibrium where the complex of 1-(1-naphthyl)ethylamine and 18-crown-6 becomes associated with β-cyclodextrin.