Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Liquid Chromatographic Resolution of Both $\pi$-Acidic and $\pi$-Basic Analytes on a Chiral Stationary Phase Derived from (S)-Tyrosine

  • Published : 1996.12.20
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Abstract

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.

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References

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