Quantitative structure–enantioselective retention relationships for chromatographic separation of arylalkylcarbinols on Pirkle type chiral stationary phases

Quantitative structure–retention (QSRR, retention factors log k 1 and log k 2 for the first and second eluted enantiomer) as well as enantioselective retention relationships (QSERR, separation factor log α) for a series of 42 chiral arylalkylcarbinols on four brush-type chiral stationary phases are derived by multiple linear regression analyses and artificial neuronal network calculations using 2D and 3D molecular descriptors including those obtained by quantum chemical calculations. Separation factors are in addition modeled by the 3D-QSAR method of comparative molecular field analysis (CoMFA). For the retention factors the LUMO energy turns out to be the most important descriptor, whereas for log α it is the hydrophobicity of the analytes. With CoMFA both the steric and electrostatic field are found to be of almost comparable significance.