Investigation of retention and chiral recognition mechanism of the alpha-aminophosphonate compounds on the derivative beta-cyclodextrin bonded stationary phase

In normal phase condition, the enantiomers of fourteen diphenyl 1-(N-benzyl oxycarbonyl)- aminoalkanephosphonates have for the first time been separate d on the phenyl carbamate derivative beta -cyclodextrin bonded phase by hig h performance liquid chromatography. The effect of temperature on the chrom atographic retention and enantioselectivity of the a - aminophosphonate com pounds has been investigated. Meanwhile, the thermodynamic studies show tha t each of the compounds has the same retention mechanism on the chiral stat ionary phase under the investigated temperature range and the chiral recogn ition process is enthalpy favored. Moreover, in order to study the retentio n and chiral recognition mechanism, the method of quantitative structure - enantioselectivity retention relationships (QSERR) was investigated from th e quantitative equations established between the chromatographic retention of enantiomers and their molecular descriptors of physico chemical properti es. In this model of QSERR, four solute - related parameters were chosen to correlate against the experimental logarithmic value of the capacity facto r to form the quantitative structure - enantioselective retention relations hips by the multivariable regression analysis and the factor analysis metho ds. The results show that on the phenyl carbamate derivative beta -cyclodex trin bonded phase, it is the parameters of logP, Angle, HOMO and LUMO that give the most contribution to the chromatographic retention of diphenyl 1- (N-benzyloxycarbonyl) - aminoalkanephosphonates and the chiral recognition is formed from the contribution of logP and Angle.