Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Chiral Recognition Models for the Liquid Chromatographic Resolution of Enantiomers on (S)-Naproxen-Derived Chiral Stationary Phase Bearing Both $\pi$-Acidic and -Basic Sites

  • Published : 1995.04.20
Download PDF
⟨ Previous Next ⟩

Abstract

As an effort to elucidate the chiral recognition mechanisms exerted by the (S)-naproxen-derived CSP bearing both π-acidic and π-basic sites, a homologues series of π-basic N-acyl-α-(1-naphthyl)alkylamines and π-acidic N-(3,5-dinitrobenzoyl)-α-amino esters were prepared and resolved. Based on the chromatographic resolution trends of the homologues series of analytes on the (S)-naproxen-derived chiral stationary phase, we proposed chiral recognition mechanisms which demonstrate that the intercalation of the substituent in the analyte molecule between the strands of bonded phase does significantly influence the enantioselectivity for resolving N-acyl-α-(1-naphthyl)alkylamines but the intercalation process is not involved in resolving N-(3,5-dinitrobenzoyl)-α-amino esters.

Keywords

References

  1. Chiral Separations By HPLC: Applications to Pharmaceutical Compounds Krstulovi$\`{c}$, A. M.(ed.)
  2. Chiral Separations by Liquid Chromatography; ACS Symposium Series 471 Ahuja, S.(ed.)
  3. J. Chromatogr. Sci. v.30 Taylor, D. R.;Maher, K.
  4. Chiral Separations by Liquid Chromatography; ACS Symposium Series 471 Perrin, S. R.;Pirkle, W. H.;Ahuja, S.(ed.)
  5. Chem. Rev. v.89 Pirkle, W. H.;Pochapsky, T. C.
  6. J. Org. Chem. v.49 Pirkle, W. H.;Hyun, M. H.
  7. J. Liq. Chromatogr. v.13 Hyun, M. H.;Kim, M. H.
  8. Chem. Lett. Hyun, M. H.;Hwang, S.-Y.;Ryoo, J.-J.
  9. J. Chromatogr. v.393 Hyun, M. H.;Pirkle, W. H.
  10. J. Chromatogr. v.462 Oi, N.;Kitahara, H.;Mathumoto, Y.;Nakajima, H.;Horikawa, Y.
  11. Chirality v.2 Tambute, a.;Siret, L.;Caude, M.;Begos, A.;Rosset, R.
  12. J. Org. Chem. v.57 Pirkle, W. H.;Welch, C. J.;Lamm, B.
  13. Chem. Lett. Hyun, M. H.;Min, C.-S.
  14. BUll. Kor. Chem. Soc. v.15 Hyun, M. H.;Jin, J. S.;Ryoo, J.-J.;Jyung, K. K.
  15. J. Liq. Chromatogr. v.14 Pirkle, W. H.;Welch, C. J.
  16. J. Org. Chem. v.48 Pirkle, W. H.;Welch, C. J.;Hyun, M. H.
  17. Org. Syn. Col. Vol. Ⅱ Barger, G.;Weichselbaum, T. E.
  18. J. Chromatogr. v.316 Pirkle, W. H.;Hyun, M. H.;Bank, B.
  19. J. Chromatogr. v.641 Pirkle, W. H.;Murray, P. G.;Burke, J. A.
  20. J. Liq. Chromatogr. v.17 Hyun. M. H.;Cho, S. M.;Ryoo, J.-J.;Kim, M. S.