EFFECTS OF ALKYL SUBSTITUENTS ON CHIRAL SEPARATION OF N-ARYLTHIAZOLIN-2-(THI)-ONE ATROPISOMERS ON TRIS (P-METHYLBENZOYL)CELLULOSE BEADS ANDCELLULOSE TRIACETATE - LIPOPHILICITY ASPECTS

The determination of lipophilicity of the title compounds allowed trea tment of the data for chiral separation (capacity factors) on CTA and CTPB according to these parameters. A linear correlation between In k' (+) and log k'w was found on both CTA and CTPB, as far as the substitu ents are situated in the plane of the aryl ring or the heterocycle. Th is correlation with a nonchiral descriptor allows treatment of capacit y factors for (-)-enantiomers as deviations from the lipophilicity lin e or derived parallels. It results in a clear description of the molec ular area affecting enantioselectivity. Application to larger alkyl de rivatives shows that the effect of the substituent should be treated o n a basis of attractive effect in the case of CTA and on the basis of attractive and repulsive effects for CTPB. (C) 1994 Wiley-Liss, Inc.