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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 18, Number 10
BKCSDE 18(10)
October 20, 1997 

 
Title
Preparation of A New HPLC Chiral Stationary Phase from (S)-Naproxen and Application in Elucidating Chiral Recognition Models
Author
Myung Ho Hyun*, Kwang Ja Kim, Kyung Kyu Jyung
Keywords
Abstract
A new HPLC chiral stationary phase (CSP 3) has been prepared by connecting N-phenyl N-propyl amide of (S)-naproxen to silica gel through the 6-methoxy-2-naphthyl group of (S)-naproxen. The new CSP has been applied in resolving a homologous series of N-(3,5-dinitrobenzoyl)-α -amino acid esters and a homologous series of N-(3,5-dinitrobenzoyl)-α -(4-alkylphenyl)alkylamines. The separation factors, α, for resolving a homologous series of N-(3,5-dinitrobenzoyl)-α-amino esters and a homologous series of N-(3,5-dinitrobenzoyl)-α -(4-alkylphenyl)alkylamines on the new CSP have been found to remain almost constant throughout the wide range of the length of the alkyl substituent of the analytes while those on the previously reported CSPs (CSP 1 and 2) which were prepared by connecting N-phenyl N-propyl amide of (S)-naproxen to silica gel through the N-propyl group increase or decrease continuously. These results are concluded to support the chiral recognition models which utilize the intercalation of the alkyl substituent of the racemic analytes between the adjacent strands of CSP 1 or 2 to rationalize the increasing or decreasing trends of separation factors.
Page
1085 - 1089
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