Factorial design approach to studying the high-performance liquid chromatographic chiral separation of N-arylthiazolin-2-(thi)one atropisomers on CHIRALCEL OJ

A two-level partial factorial design was applied to quantify the effect (including the lipophilicity effect) of five selected structural parameters on the retention and chiral separation of atropisomers of N-arylthiazolin-2-(thi)one atropisomers CHIRALCEL OJ in hexane-2-propanol (9:1) and ethanol eluents. The linear correlation between the capacity factors on CHIRALCEL OJ and the lipophilicity parameter indicates the non-discriminating lipophilicity contribution of structural factors on the retention of each enantiomer. Treatment of the lipophilicity freed data indicates attractive or repulsive structural effects responsible for the discriminating interactions. This results in a clear description of the molecular area involved in the enantioselective retention of the tested compounds on CHIRALCEL OJ, thus facilitating the proposition of a chiral recognition mechanism.