ENANTIOMERIC SEPARATION OF AMINES BY GAS CHROMATOGRAPHY USING ACETYL-DERIVATIZED BETA-CYCLODEXTRIN AS STATIONARY PHASE

Abstract

The enantioseparation of 49 trifluoroacetyl amine derivatives was studied by gas chromatography using heptakis(2,3-di-O-acetyl-6-O-tert-butyldimethylsilyl)-beta-cyclodextrin (or BSiAc) as a chiral stationary phase. The effects of temperature and amine structure (type and position of substitution) on retention and enantioselectivity were studied. BSiAc could resolve enantiomers of 45 amines. For 1-phenylethylamines, the position of substitution played a major role on enantioseparation than the type of substitution: analytes with meta-substitution showed good enantioseparation. The effect of type of substitution at the stereogenic center was also investigated. BSiAc showed better enantioseparation towards 1-phenylpropylamines or 1-aminoindans than 1-phenylethylamines. However, BSiAc showed poor or no enantioseparation towards phenyl phenyl methanamines which have a large phenyl group at the stereogenic center. Among all analytes tested in this study, 3CF3 showed strong temperature dependency and could be completely enantioseparated with the shortest analysis time.