SEPARATION OF N-ARYLTHIAZOLINE-2-(THI)-ONE ATROPISOMERS ON P-METHYLBENZOYL CELLULOSE BEADS - A FACTORIAL DESIGN APPROACH

A two level full factorial design has been applied to quantify the eff ect of three selected structural parameters on the capacity factors an d chiral separation of atropisomers in N-arylthiazoline-2-(thi)-ones d erivatives on tris(p-methylbenzoyl) cellulose beads. The behavior of t he two enantiomers is influenced by different factors which might resu lt from different retention sites within the same stationary phase. It appears that the two enantiomers behave independently on the CSP, the order of elution and separation being controlled by a minor steric mo dification in a very precise location in the molecule for one enantiom er. The methodology of the experimental design allows the comparison o f equations generated from data issued from designed compounds. These equations afford much more information than the step by step compariso n of individual molecules. In our case, the tris(p-methylbenzoyl)cellu lose beads and microcrystalline cellulose triacetate appear as complem entary CSPs for the resolution of atropisomers of the series studied. (C) 1993 Wiley-Liss, Inc.