INVESTIGATION ON THE CHIRAL DISCRIMINATION MECHANISM USING AN AXIALLYASYMMETRIC BINAPHTHALENE-BASED STATIONARY-PHASE FOR HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY

The chiral discrimination mechanism of 3,5-dinitrophenyl-derivatized e nantiomeric alcohols, amines and carboxylic acids using a chiral stati onary phase (CSP) prepared by bonding (aS)-1,1'-binaphthyl-2,2'-dicarb oxylic acid to 3-aminopropylsilanized silica gel was investigated. Stu dies of the elution behaviour of a series of structurally related anal ytes on the CSP and H-1 NMR measurements of a solubilized model compou nd of the CSP and analytes indicated that a pi-donor-acceptor interact ion between one of the naphthalene planes of the CSP and the 3,5-dinit rophenyl ring of the analyte cooperates with the dipole stacking inter action between two sets of amide linkages of the CSP and the analytes to determine the stability of the diastereomeric adsorbates.