Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Preparation of a New Chiral Stationary Phase Bearing Both $\pi$-Acidic and -Basic Sites from (S)-Naproxen for the Liquid Chromatographic Resolution of Enantiomers

  • Hyun Myung Ho (Department of Chemistry, Pusan National University) ;
  • Jin Jong Sung (Department of Chemistry, Pusan National University) ;
  • Ryoo Jae-Jeong (Department of Chemistry, Pusan National University) ;
  • Jyung Kyung Kyu (Department of Chemistry Education, Pusan National University)
  • Published : 1994.06.20
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Abstract

A new chiral stationary phase (CSP) for the liquid chromatographic resolution of enantiomers was prepared from (S)-naproxen and 3,5-dinitroaniline. The 6-alkoxy-2-naphthyl group of the CSP was presumed to act as a ${\pi}$-basic interaction site for resolving ${\pi}$-acidic racemates while the 3,5-dinitroanilide group of the CSP was presumed to play a role as a ${\pi}$-acidic interaction site for resolving ${\pi}$-basic racemates. From the chromatographic resolution trends of N-alkylamide derivatives of ${\alpha}$-arylalkylamines on the CSP prepared, the chiral recognition mode involving the intercalation of the amide alkyl chain of the less retained enantiomers between the connecting tethers of the CSP was proposed.

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References

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