In normal phase condition, the enantiomers of fourteen diphenyl 1-(N- benzyloxycarbonyl)-aminoalkanephosphonates have for the first time been separated on the phenyl carbamate derivative β-cy-clodextrin bonded phase by high performance liquid chromatographyl. The effect of temperature on the chromatographic retention and enantioselectivity of the α-aminophosphonate compounds has been investigated. Mean while, the thermodynamic studies show that each of the compounds has the same retention mechanism on the chiral stationary phase under the investigated temperature range and the chiral recognition process is enthalpy favored. Moreover, in order to study the retention and chiral recognition mechanism, the method of quantitative structure-enantioselectivity retention relationships (QSERR) was investigated from the quantitative equations established between the chromatographic retention of enantiomers and their molecular descriptors of physico chemical properties. In this model of QSERR, four solute-related parameters were chosen to correlate against the experimental logarithmic value of the capacity factor to form the quantitative structure-enantioselective retention relationships by the multivarible regression analysis and the factor analysis methods. The results show that on the phenyl carbamate derivative β-cyclodextrin bonded phase, it is the parameters of logP, Angle, HOMO and LUOM that give the most contribution to the chromatographic retention of diphenyl 1-(N-benzyloxycarbonyl)- aminoalkanephosphonates and the chiral recognition is formed form the contribution of lowP and Angle.

Key words: CYCLODEXTRIN, STATIONARY PHASE, QUANTITATIVE STRUCTURE ACTIVITY RELATIONSHIP, RETENTION TIME, IDENTIFICATION, CHIRAL REAGENT, PHOSPHOAMIDIC ACID P, BONDING PHASE, HIGH SPEED LIQUID CHROMATOGRAPHY