Investigation of the Crystal Structure for the Direct Chiral Separation Model in High-Performance Liquid Chromatography.

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(R, S)-N-(3, 5-dinitrophenyl)-α-methylbenzeneacetamide [(R, S)-PPA-DNA] can be resolved into its enantiomer on the chiral stationary phase (CSP) which chemically bonded with (S)-α-methyl-1-naphthylamine. To investigate the mechanism of this chiral discrimination in liquid chromatography, an X-ray crystallographic study of two diastereomeric equimolar complexes was performed. (S)-N Acetyl-α-methyl-1-naphthylamine [(S)-NEA-a] and (R), (S)-PPA-DNA were used as models of the CSP and the analyte, respectively. The crystal structures of both diastereomeric complexes were clarified so that the hydrogen bond and the π-π donor-acceptor intermolecular interaction dominated the chiral discrimination, suggesting that the chiral discrimination was caused by the differences in the binding force and in the number of intermolecular interactions within a combination of the CSP model and the analyte in suitable association. This interpretation of the result of X-ray crystallography agreed with the elution order on chromatography. The correlation between the crystal structure and the proton nuclear magnetic resonance (NMR) spectroscopy is also discussed.
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