TY - JOUR
T1 - Chiral recognition using a conformationally rigid chiral stationary phase derived from amino-ε-carprolactam
AU - Han, Hyo Kyung
AU - Hong, Joon Hee
AU - Carey, James R.
AU - Kang, Jong Seong
AU - Lee, Wonjae
PY - 2014/11/26
Y1 - 2014/11/26
N2 - The mechanisms underlying chiral recognition of enantiomer separation using a conformationally rigid chiral stationary phase (CSP 2) derived from N-3,5-dinitrobenzoyl (DNB) amino-ε-carprolactam, a CSP structurally related to DNB leucine derived CSP 1, were investigated. Chromatographic comparisons of the resolution for two typical types of analytes were made on CSPs 1 and 2. For enantioseparation of N-acyl derivatives of 1-(1-or 2-naphthyl)ethylamine, all separation factors for DNB leucine derived CSP 1 were greater than those for DNB ε-carprolactam derived CSP 2. On the other hand, all separation factors for CSP 2 were much greater than those for CSP 1 when resolving DNB leucine derivatives. In any case, the overall chiral recognition mechanism of CSP 2 might be similar to that of CSP 1. However, it is thought that the conformationally rigid structure and/or enhanced electron density of the carbonyl group as a tertiary amide of CSP 2 could be responsible for different levels of chiral recognition relative to CSP 1, depending upon the analytes examined.
AB - The mechanisms underlying chiral recognition of enantiomer separation using a conformationally rigid chiral stationary phase (CSP 2) derived from N-3,5-dinitrobenzoyl (DNB) amino-ε-carprolactam, a CSP structurally related to DNB leucine derived CSP 1, were investigated. Chromatographic comparisons of the resolution for two typical types of analytes were made on CSPs 1 and 2. For enantioseparation of N-acyl derivatives of 1-(1-or 2-naphthyl)ethylamine, all separation factors for DNB leucine derived CSP 1 were greater than those for DNB ε-carprolactam derived CSP 2. On the other hand, all separation factors for CSP 2 were much greater than those for CSP 1 when resolving DNB leucine derivatives. In any case, the overall chiral recognition mechanism of CSP 2 might be similar to that of CSP 1. However, it is thought that the conformationally rigid structure and/or enhanced electron density of the carbonyl group as a tertiary amide of CSP 2 could be responsible for different levels of chiral recognition relative to CSP 1, depending upon the analytes examined.
KW - 3,5-dinitrobenzoyl leucine
KW - amino-ε-carprolactam
KW - chiral recognition
KW - chiral stationary phase
KW - conformationally rigid
KW - enantiomer separation
UR - http://www.scopus.com/inward/record.url?scp=84902977696&partnerID=8YFLogxK
U2 - 10.1080/10826076.2013.807467
DO - 10.1080/10826076.2013.807467
M3 - Article
AN - SCOPUS:84902977696
SN - 1082-6076
VL - 37
SP - 2725
EP - 2732
JO - Journal of Liquid Chromatography and Related Technologies
JF - Journal of Liquid Chromatography and Related Technologies
IS - 19
ER -