Skip to main content
Log in

Chromatographic studies on the inclusion of isomeric dimethylnaphthalenes by β- and γ-cyclodextrin

  • Originals
  • Published:
Chromatographia Aims and scope Submit manuscript

Summary

Reversed-phase high performance liquid chromatography and gas-liquid chromatography have been applied to studies on the complexation of cyclodextrins with isomeric dimethylnaphthalenes. Both β and γ-cyclodextrins have been found to form inclusion complexes with dimethylnaphthalenes. With the exception of the complex of 1,8-dimethylnaphthalene with β-cyclodextrin, all the other complexes under investigation are of moderate stability. The remarkable affinity of β-cyclodextrin for 1,8-dimethylnaphthalene has been observed by both GC and HPLC. The stability constant of this complex was always about 1.5–2.0 orders of magnitude greater than the corresponding value for the other isomers. The chromatographic data suggest that there is an especially good fit of the 1,8-dimethylnaphthalene molecule into the β-cyclodextrin cavity. The importance of studying the complicated phenomena of complexation by cyclodextrin using various experimental and theoretical methods is stressed.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. F. Cramer, Angew. Chem.,868, 115 (1956);Y. Matsui, Bull. Chem. Soc. Japan,55, 1246 (1982) and references cited therein.

    Google Scholar 

  2. F. Cramer, W. Kampe, J. Chem. Soc.,87, 1115 (1965).

    Article  Google Scholar 

  3. Y. Matsui, Bull. Chem. Soc. Japan,55, 1246 (1982);D. E. Tutt, N.A. Schwartz, J. Chem. Soc., Chem. Commun., 113 (1970).

    Google Scholar 

  4. P.G. Manor, W. Saenger, Nature (London),237, 392 (1972);W. Saenger, M. Noltenmeyer, Angew. Chem., Int. Ed. Engl.,13, 552 (1974).

    Article  Google Scholar 

  5. R. J. Bergeron, D. Rowan, III, Bioorg. Chem.,5, 425 (1976);A. Orstan, J. B. Alexander Ross, J. Phys. Chem.,91, 2739 (1987).

    Article  Google Scholar 

  6. M. Sakurai, M. Kitagawa, H. Hoshi, J. Ynoue, R. Chujo, Carbohydr. Res.,198, 181 (1990);M. Koiyama, M. L. Bender, J. Am. Chem. Soc.,100, 2259 (1978).

    Article  Google Scholar 

  7. D. Sybilska, J. Lipkowski, J. Wójcicki, J. Chromatogr.,253, 95 (1982).

    Article  Google Scholar 

  8. D. Sybilska, T. Kościelski, J. Chromatogr.,261, 362 (1983).

    Google Scholar 

  9. J. Żukowski, D. Sybilska, J. Jurczak, Anal. Chem.,57, 2215 (1985).

    Article  Google Scholar 

  10. J. Dębowski, D. Sybilska, J. Chromatogr.,353, 409 (1989).

    Article  Google Scholar 

  11. H. Lamparczyk, P. Zarzycki, R. Ochocka, M. Asztemborska, D. Sybilska, Chromatogr.,31, 157 (1991).

    Google Scholar 

  12. D. Sybilska, J. Jurczak, Carbohydr. Res.,192, 243 (1989).

    Article  Google Scholar 

  13. H. Dodziuk, J. Sitkowski, L. Sefaniak, J. Jurczak, D. Sybilska, J. Chem.Soc., Chem. Commun.,207 (1992).

  14. H. Dodziuk, K. Nowiński, to be published.

  15. J. Dębowski, D. Sybilska, J. Jurczak, J. Chromatogr.,237, 303 (1982).

    Article  Google Scholar 

  16. D. Sybilska, in “Ordered Media in Chemical Separations”, W. L. Hinze and D. W. Armstrong, Eds., ACS Symposium Series,342, 1987, p. 218.

  17. D. W. Armstrong, F. Nome, L. A. Spino, T. D. Golden, J. Am. Chem. Soc.,108, 1416 (1986).

    Google Scholar 

  18. K. Fujimura, T. Ueda, M. Kitagawa, H. Takayanogi, T. Ando, Anal. Chem.58, 2668 (1986).

    Article  Google Scholar 

  19. J. H. Purnell in A. B. Littlewood, Ed., “Gas Chromatography”, Institute of Petroleum, Ondon, 1966, p. 3.

    Google Scholar 

  20. C. Eon, C. Pommier, G. Guiochon, J. Phys. Chem.,75, 2632 (1971).

    Article  Google Scholar 

  21. H. Dodziuk, J. Sitkowski, L. Stefaniak, D. Sybilska, J. Jurczak, to be published.

  22. N. L. Allinger, Adv. Phys. Org. Chem.,13, 1 (1976);E. Osawa, H. Musso, Angew. Chem.,95, 1 (1983).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Sybilska, D., Asztemborska, M., Bielejewska, A. et al. Chromatographic studies on the inclusion of isomeric dimethylnaphthalenes by β- and γ-cyclodextrin. Chromatographia 35, 637–642 (1993). https://doi.org/10.1007/BF02267929

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02267929

Key Words

Navigation