STUDY OF CHIRAL RECOGNITION MECHANISM OF O,O-DIETHYL ENZENESULFONAMINDO)-ARYL(ALKYL)-METHYLPHOSPHONATES BY HPLC WITH A SERIES OF CSPS

Five chiral stationary phases (CSPs) were used to separate the enantio mers of a series of O,O-diethyl (p-methyl-benzenesulfonamindo)- aryl(a lkyl)-methylphosphonates. A chiral recognition mechanism was presented to explain the resolution of these compounds. Results show that CSP w ith strong pi-acceptor 3,5-dinitrobenzoyl group and high steric hindra nce has the best resolution ability in chiral separation of O, O-dieth yl (p-methyl-benzenesulfonamindo)- aryl (alkyl)-methylphosphonates. Wh en a CSP has just a strong pi-acceptor 3,5-dinitrobenzoyl or high ster ic hindrance it does not have good chiral resolution ability. The chir al recognition is more difficult when the CSP has more than one asymme tric center.