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 atropisomers on Chiralcel OJ chiral stationary phase was investigated by quantifying the effects on the retention and enantioselectively of the alkyl substitution in the series Me, Et, iPr, tBu, in the key position blocking the rotation and inducing chirality on both phenyl and heterocycle portions of the tested compounds. The response equation in a two-level 2 4 factorial design and the linear correlations between the capacity factors on Chiralcel OJ and the liphophilicity parameter were used. This treatment of the data results in the description of the molecular area involved in the enantioselective retention, in the case of a substitution providing complex steric and lipophilic interactions, thus allowing the validation of the proposed chiral recognition model.