• Bulletin of the Korean Chemical Society
• /
• v.25 no.12
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• pp.1977-1979
• /
• 2004

• Bulletin of the Korean Chemical Society
• /
• v.16 no.10
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• pp.977-980
• /
• 1995

A new chiral stationary phase (CSP 2) derived from cyclohexylamide of (S)-naproxen has been prepared. CSP 2 has shown greater enantioselectivities for the two enantiomers of N-(3,5-dinitrobenzoyl)-a-amino esters and amides than the CSP derived from 3,5-dimethylanilide of (S)-naproxen (CSP 1) as expected from the reciprocity conception of chiral recognition. However, CSP 2 has been found to be worse than CSP 1 in resolving N-(3,5-dinitrobenzoyl)-a-arylalkylamines, supporting the previously proposed chiral recognition mechanism which utilizes the 3,5-dimethylphenyl group of CSP 1 as an alternative π-basic interaction site. In addition, CSP 2 has been found to be reasonably good in resolving the two enantiomers of a variety of other π-acidic racemates.