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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 17, Number 12
BKCSDE 17(12)
December 20, 1996 

Liquid Chromatographic Resolution of Both π-Acidic and π-Basic Analytes on a Chiral Stationary Phase Derived from (S)-Tyrosine
Myung Ho Hyun, Chung-Sik Min
Chiral recognition models for resolving π-basic N-acyl-α-(1-naphthyl)alkylamines and π-acidic N-(3,5-dinitrobenzoyl)-α-amino alkyl esters on a (S)-tyrosine-derived chiral stationary phase (CSP) containing both π-basic and π-acidic interaction site have been proposed. In the models, the CSP was supposed to interact with the analytes through the π-π interaction between the 3,5-dinitrophenyl or the 3,5-dimethylphenyl group of the CSP and the 1-naphthyl or the 3,5-dinitrophenyl group of the analyte, and through the hydrogen bonding interaction between the appropriate N-H hydrogen of the CSP and the appropriate carbonyl oxygen of the analyte. In this instance, the alkyl substituent of the pertinent enantiomer of the analyte was found to intercalate between the adjacent strands of the bonded phase and consequently control the trends of the separation factors.
1117 - 1123
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