HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY OF DIAMINE ENANTIOMERS AS SCHIFF-BASES ON A CHIRAL STATIONARY-PHASE

A high-performance liquid chromatographic method for the enantiomeric analysis of chiral 1,2-diamines is described. By derivatization with benzaldehyde, aliphatic and aromatic 1,2-diamines were converted into Schiff base derivatives. Separation of the enantiomeric derivatives was performed on a commercially available cellulose tris(3,5-dimethylphenylcarbamate) chiral stationary phase. To investigate the effect of the reagent structure on enantioseparation, a series of twenty ring-substituted benzaldehydes were reacted with an aliphatic and an aromatic diamine. The influence of the type of substituent of the benzaldehyde reagent on the enantioselectivity obtained for Schiff base derivatives is discussed.