Quantitative structure-enantioselective retention relationships for chromatographic separation of arylalkylcarbinols on Pirkle type chiral stationaryphases

Quantitative structure-retention (QSRR, retention factors log k(1) and log k(2) for the first and second eluted enantiomer) as well as enantioselectiv e retention relationships (QSERR, separation factor log alpha) for a series of 42 chiral arylalkylcarbinols on four brush-type chiral stationary phase s are derived by multiple linear regression analyses and artificial neurona l network calculations using 2D and 3D molecular descriptors including thos e obtained by quantum chemical calculations. Separation factors are in addi tion modeled by the SD-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 alpha it is the hydrophobicity of th e analytes. With CoMFA both the steric and electrostatic field are found to be of almost comparable significance. (C) 2001 Elsevier Science B.V. All r ights reserved.