TY - JOUR
T1 - Investigation on the chiral discrimination mechanism using an axially asymmetric binaphthalene-based stationary phase for high-performance liquid chromatography
AU - Oi, Shuichi
AU - Ono, Hiroyuki
AU - Tanaka, Hideyuki
AU - Matsuzaka, Yutaka
AU - Miyano, Sotaro
N1 - Funding Information:
We are grateful to the Ministry of Education, Science and Culture, Japan (Grant-in-Aid No. 02555177)a, nd to Tosoh for financial support.
PY - 1994/1/21
Y1 - 1994/1/21
N2 - The chiral discrimination mechanism of 3,5-dinitrophenyl-derivatized enantiomeric alcohols, amines and carboxylic acids using a chiral stationary phase (CSP) prepared by bonding (aS)-1,1′-binaphthyl-2,2′-dicarboxylic acid to 3-aminopropylsilanized silica gel was investigated. Studies of the elution behaviour of a series of structurally related analytes on the CSP and 1H NMR measurements of a solubilized model compound of the CSP and analytes indicated that a π-donor-acceptor interaction between one of the naphthalene planes of the CSP and the 3,5-dinitrophenyl ring of the analyte cooperates with the dipole stacking interaction between two sets of amide linkages of the CSP and the analytes to determine the stability of the diastereomeric adsorbates.
AB - The chiral discrimination mechanism of 3,5-dinitrophenyl-derivatized enantiomeric alcohols, amines and carboxylic acids using a chiral stationary phase (CSP) prepared by bonding (aS)-1,1′-binaphthyl-2,2′-dicarboxylic acid to 3-aminopropylsilanized silica gel was investigated. Studies of the elution behaviour of a series of structurally related analytes on the CSP and 1H NMR measurements of a solubilized model compound of the CSP and analytes indicated that a π-donor-acceptor interaction between one of the naphthalene planes of the CSP and the 3,5-dinitrophenyl ring of the analyte cooperates with the dipole stacking interaction between two sets of amide linkages of the CSP and the analytes to determine the stability of the diastereomeric adsorbates.
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U2 - 10.1016/0021-9673(94)85008-9
DO - 10.1016/0021-9673(94)85008-9
M3 - Article
AN - SCOPUS:0028327145
SN - 0021-9673
VL - 659
SP - 75
EP - 86
JO - Journal of Chromatography A
JF - Journal of Chromatography A
IS - 1
ER -