Mechanism of capillary electrophoresis enantioseparations using a combination of an achiral crown ether plus cyclodextrins

The addition of an achiral crown ether (18-crown-6) to a cyclodextrin-based separation can significantly affect the capillary electrophoresis (CE) enantioresolution of organic racemates that contain a primary amine functional group. In most cases an enhancement of the enantioseparation was observed. However, there are also cases where the addition of 18-crown-6 was detrimental to a cyclodextrin-based CE enantioseparation. The effect of concentration of the two complexing additives as well as the effect of pH and added potassium ion were examined. A specific three-body complex involving simultaneous, dual inclusion complex formation can be used to explain both the enhanced and diminished enantioselectivities observed when 18-crown-6 is added to the run buffer. (C) 1998 Elsevier Science B.V.