Chromatographia

, Volume 48, Issue 5–6, pp 388–394 | Cite as

A simple model for RPLC retention and selectivity of imidazole enantiomers using β-cyclodextrin as chiral selector

  • N. Morin
  • Y. C. Guillaume
  • J. -C. Rouland
Originals

Summary

Using reversed phase liquid chromatography (RPLC), this paper investigates the enantioselectivity variations, in a series of weak polar R, S-imidazole derivatives, with β-cyclodextrin concentration in the mobile phase over a wide range of column temperatures. These compounds are used for the treatment of onychomycosis. The selectivity data obtained were assessed using a chiral recognition model, based on the formation of complexes between the solute molecule and the cyclodextrin cavity. Gibbs Helmholtz parameters (Δ(ΔH), Δ(ΔS)) between R- and S- enantiomers were determined from the logarithm of the separation factor, α, versus the reciprocal of the temperature plots. The thermodynamic results predicted that the enantioselectivity mechanism was related to both the solute's bulkiness and the asymmetric carbon atom configuration.

Key Words

Column liquid chromatography Imidazole derivatives β-Cyclodextrin Enantioselectivity 

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References

  1. [1]
    R. H. Pullen, J. J. Brennan, G. Patonay, J. Chromatogr. A691, 187 (1995).CrossRefGoogle Scholar
  2. [2]
    E. Ameyibor, J. T. Stewart, J. Liq. Chrom. & Rel. Technol.6, 855 (1997).Google Scholar
  3. [3]
    J. Szejtli, Cyclodextrins and their inclusion complexes, Akadémiai Kiadó, Budapest, 1982.Google Scholar
  4. [4]
    R. Furuta, T. Doi, J. Chromatogr. A708, 245 (1995).CrossRefGoogle Scholar
  5. [5]
    G. Crini, Y. Lekchiri, M. Morcellet, Chromatographia40, 296 (1995).CrossRefGoogle Scholar
  6. [6]
    R. Furuta, H. Nakazawa, J. Chromatogr.625, 231 (1992).CrossRefGoogle Scholar
  7. [7]
    H. Lamparczyk, P. K. Zarzycki, J. Nowakowska, J. Chromatogr. A668, 413 (1994).CrossRefGoogle Scholar
  8. [8]
    M. Pedersen, M. Edelsten, V. F. Nielsen, A. Scarpellini, S. Skytte, C. Slot, Int. J. Pharm.90, 247 (1993).CrossRefGoogle Scholar
  9. [9]
    H. Van Doorne, E. H. Bosch, C. F. Lerk, Pharmaceut. Weekl. Sci. Ed.10, 80 (1988).CrossRefGoogle Scholar
  10. [10]
    M. Pedersen, Drug Develop. Ind. Pharm.19, 439 (1993).Google Scholar
  11. [11]
    B. Maupas, S. Letellier, F. Guyon, J. Inclusion Phenom. Mol. Recogn. in Chemistry23, 259 (1996).CrossRefGoogle Scholar
  12. [12]
    Y. C. Guillaume, C. Guinchard, Chromatographia40, 193 (1995).CrossRefGoogle Scholar
  13. [13]
    Y. C. Guillaume, C. Guinchard, Chromatographia41, 84 (1995),CrossRefGoogle Scholar
  14. [14]
    N. Morin, Y. C. Guillaume, E. Peyrin, J.-C. Rouland, J. Chromatogr. A, in press.Google Scholar
  15. [15]
    Y. C. Guillaume, C. Guinchard, J. Liq. Chrom.17, 1443 (1994).Google Scholar
  16. [16]
    Y. C. Guillaume, C. Guinchard, J. Chromatogr. Sci.33, 204, (1995).Google Scholar
  17. [17]
    L. A. Cole, J. G. Dorsey, Anal. Chem.64, 1317 (1992).CrossRefGoogle Scholar
  18. [18]
    L. A. Cole, J. G. Dorsey, K. A. Dill, Anal. Chem.64, 1324 (1992).CrossRefGoogle Scholar
  19. [19]
    Y. C. Guillaume, C. Guinchard, Anal. Chem.68, 2869 (1996).CrossRefGoogle Scholar
  20. [20]
    Y. C. Guillaume, C. Guinchard, Anal. Chem.69, 183 (1997).CrossRefGoogle Scholar

Copyright information

© Friedr. Vieweg & Sohn Verlagsgesellschaft mbH 1998

Authors and Affiliations

  • N. Morin
    • 1
  • Y. C. Guillaume
    • 2
  • J. -C. Rouland
    • 1
  1. 1.Laboratoire de Chimie Physique et MinéraleBesançon CedexFrance
  2. 2.Laboratoire de Chimie AnalytiqueFaculté de Médecine et de PharmacieBesançon CedexFrance

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