Under normal phase condition, the enantiomers of a series of diphenyl 1-(N-benzyloxycarbonly)-aminoalkanephosphonates have first been separated on the two commercial chiral stationary phases of cyclodextrin- typed CYCLOBOND I SN and Pirkle-typed Sumichiral OA 4700 by high performance liquid chromatography. In order to study the retention and chiral recognition mechanism, the method of quantitative structure- enantioselectivity retention relationships was investigated from the quantitative equations established between the chromatographic retention of enantiomers and their molecular descriptors of physico-chemical properties. The mathematical statistical method is the multiple stepwise regression analysis in which the optimized equation can be obtained by choosing and deleting proper parameters according to the mathematical significant test. The results show the on the two commercial chiral stationary phases, the organophosphorus compounds of diphenyl 1-(N-benzyloxycarbonyl)- aminoalkanephosphonates have different retention and chiral recognition mechanism although the two commercial chiral stationary phases have the same Pirkle-typed chiral group and under the normal phase condition. On the chiral stationary phases of cyclodextrin- typed CYCLOBOND I SN, it is the parameters of logP and Angle that give the most contribution to the chromatographic chiral separation of diphenyl 1-(N-benzyloxycarbonyl)- aminoalkanephosphonates. Nevertheless, it is the contribution of the parameters of locD and TE that forms the chiral recognition on the chiral stationary phases of Pirkle-typed Sumichiral OA 4700 about these organophosphorus compounds.

Key words: PHOSPHONIC ACID ESTER, ORGANO PHOSPHORUS COMPOUNDS, HIGH SPEED LIQUID CHROMATOGRAPHY, STATIONARY PHASE, ISOMER, SELECTIVITY