Enantioselective correlation between retention factor and lipophilicity index in chiral separation on cellulose and amylose tris(3,5-dimethylphenylcarbamate) CSPs in reversed mode: A case study

For a series of alkyl substituted N-arylthiazoline-2 (thi) one atropisomers 1-14, lipophilicity indexes log kw obtained by polycratic RP-HPLC were com pared to In k(+)-S and In k(-)-R obtained on CHIRALCEL OD-R-(R) (reversed m ode) and CHIRALPAK AD-RH (R) (reversed mode). Linear correlations were obta ined in most cases. It appears that the correlation lines for R and S enant iomers may be parallel, convergent, or divergent, accounting for the observ ed alpha variation in going from methyl to tert-butyl series. Some tentativ e hypothesis are given as future investigation routes. (C) 2000 Wiley-Liss, Inc.