INVESTIGATION INTO THE CHIRAL RECOGNITION MECHANISM OF N-ARYLTHIAZOLIN-2(THI)ONE ATROPISOMERS ON CHIRALCEL OJ BY FACTORIAL DESIGN AND LIPOPHILICITY APPROACHES

The chiral recognition mechanism of N-arylthiazolin-2(thi)one atropiso mers on Chiralcel OJ chiral stationary phase was investigated by quant ifying the effects on the retention and enantioselectivity of the alky l substitution in the series Me, Et, iPr, tBu, in the key position blo cking the rotation and inducing chirality on both phenyl and heterocyc le portions of the tested compounds. The response equation in a two-le vel 2(4) factorial design and the linear correlations between the capa city factors on Chiralcel OJ and the lipophilicity parameter were used . This treatment of the data results in the description of the molecul ar area involved in the enantioselective retention, in the case of a s ubstitution providing complex steric and lipophilic interactions, thus allowing the validation of the proposed chiral recognition model.