title: Modeling the chromatographic enantioseparation of aryl- and hetarylcarbinols on ULMO, a brush-type chiral stationary phase, by 3D-QSAR techniques.
abstract: The enantiomers of a series of chiral aryl- and hetaryl-carbinols were separated on a chiral stationary phase (ULMO) based on (S,S)-3,5-dinitrobenzoylated 1,2-diphenylethane-1,2-diamine. In all cases, the homochiral analogs of (S)-1-phenylethanol (mostly also S-enantiomers) were retained more. Log alpha values were modeled with the aid of the 3D-QSAR techniques CoMFA (comparative molecular field analysis) and CoMSIA (comparative molecular similarity indices analysis) as well as a descriptor based on normal mode eigenvalues (EVA). Partial least-squares analysis with two (CoMSIA) or three (CoMFA, EVA) latent variables on a set of 22 training analytes gives cross-validated correlation coefficients q(2) = 0.85-0.91 and conventional correlation coefficients r(2) = 0.94-0.99. The quantitative structure-enantioselective retention relationships derived thereby were used to predict the separation factors of the test set, containing also hetaryl-carbinols, e.g., furan and thiophene analogs, with good accuracy.
authors.affiliation: Institut für Chemie, Karl-Franzens Universität Graz, Graz, Austria. walter.fabian@uni-graz.at
authors.forename: Walter M F
authors.initials: WM
authors.lastname: Fabian
authors.forename: Wolfgang
authors.initials: W
authors.lastname: Stampfer
authors.forename: Monika
authors.initials: M
authors.lastname: Mazur
authors.forename: Georg
authors.initials: G
authors.lastname: Uray