Skip to main content
Log in

Evaluation of solute hydrophobicity by reversed-phase high performance liquid chromatography using aqueous binary mobile phases

  • Originals
  • Published:
Chromatographia Aims and scope Submit manuscript

Summary

The dependence of the capacity factor (k′) on the concentration of the organic modifier (D) in the aqueous binary mobile phase in reversed-phase high-performance liquid chromatography has been investigated to evaluate the hydrophobicity of the solute molecule. The r-values, defined as the slope of log k′ vs. log(1/D) plots, were measured for various solutes and related to the non-polar surface area and the partition coefficients. The r-value was found to be a good indication of solute hydrophobicity. Detailed investigation of the results allowed to consider statistically the molecular posture of the solute adsorbed onto the stationary alkyl ligand.

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. C. Hansch, in “Drug Design”E. J. Ariens, ed., Academic Press, New York, Vol. 1 (1971); p. 271.

    Google Scholar 

  2. C. Hansch, A. Leo, “Substituent Constants for Correlation Analysis in Chemistry and Biology”, Wiley, New York, (1979).

    Google Scholar 

  3. C. Hansch, T. Fujita, J. Am. Chem. Soc.86, 1616 (1964).

    CAS  Google Scholar 

  4. C. Hansch, J. Med. Chem.19, 1 (1976).

    CAS  Google Scholar 

  5. T. Fujita, Adv. Chem. Ser.114, 1 (1972).

    CAS  Google Scholar 

  6. J. M. McCall, J. Med. Chem.18, 549 (1975).

    Article  CAS  Google Scholar 

  7. A. Hulshoff, J. H. Perrin, J. Chromatogr.129, 263 (1976).

    CAS  Google Scholar 

  8. R. M. McCormick, B. L. Karger, Anal. Chem.52, 2249 (1980)

    Article  CAS  Google Scholar 

  9. E. H. Slaats, W. Markovski, J. Fekete, H. Poppe, J. Chromatogr.207, 299 (1981).

    Article  CAS  Google Scholar 

  10. W. E. Hammers, G. J. Meurs, C. L. De Ligny, J. Chromatogr.246, 169 (1982).

    Article  CAS  Google Scholar 

  11. C. S. Koch, F. Koster, G. H. Findenegg, J. Chromatogr.406, 257 (1987).

    Article  CAS  Google Scholar 

  12. K. E. Bij, C. Horvath, W. R. Melander, A. Nahum, J. Chromatogr.203, 65 (1981).

    CAS  Google Scholar 

  13. N. E. Tayar, A. Tsantili-Kakoulidou, T. Roethlisberger, B. Testa, J. Gal, J. Chromatogr.439, 237 (1988).

    Google Scholar 

  14. P. R. W. Scott, C. F. Simpson, J. Chromatogr.197, 11 (1980).

    Article  CAS  Google Scholar 

  15. C. R. Yonker, T. A. Zwier, M. F. Burke, J. Chromatogr.241, 257 (1982).

    CAS  Google Scholar 

  16. A. Ben-Naim, “Water and Aqueous Solutions”, Plenum Press, New York, (1974); p. 363.

    Google Scholar 

  17. N. Tanaka, H. Goodell, B. L. Karger, J. Chromatogr.158, 233 (1978).

    CAS  Google Scholar 

  18. M. J. Kamlet, M. H. Abraham, P. W. Carr, R. M. Doherty, R. W. Taft, J. Chem. Soc. Perkin Trans.II 2087 (1988).

    Google Scholar 

  19. K. Jinno, K. Kawasaki, J. Chromatogr.316, 1 (1984).

    Article  CAS  Google Scholar 

  20. T. Braumann, J. Chromatogr.373, 191 (1986).

    Article  CAS  Google Scholar 

  21. D. J. Minick, J. H. Frenz, M. A. Patrick, D. A. Brent, J. Med. Chem.31, 1923 (1988).

    Article  CAS  Google Scholar 

  22. D. J. Minick, J. J. Sabatka, D. A. Brent, J. Liq. Chromatogr.10, 2565 (1987).

    CAS  Google Scholar 

  23. P. J. Schoenmakers, H. A. H. Billiet, R. Tijssen, L. De Galan, J. Chromatogr.149, 519 (1978).

    Article  CAS  Google Scholar 

  24. P. Jandera, J. Chromatogr.314, 13 (1984).

    Article  CAS  Google Scholar 

  25. D. E. Martire, R. E. Boehm, J. Phys. Chem.87, 1045 (1983).

    CAS  Google Scholar 

  26. K. A. Dill, J. Phys. Chem.91, 1980 (1987).

    Article  CAS  Google Scholar 

  27. L. R. Snyder, in “High Performance Liquid Chromatography”C. Horvath, ed., Academic Press, New York, Vol. 3 (1983); p. 157.

    Google Scholar 

  28. E. Soczewinski, Anal. Chem.41, 179 (1969).

    Article  CAS  Google Scholar 

  29. E. Soczewinski, T. Dzido, Chromatographia22, 25 (1986).

    CAS  Google Scholar 

  30. F. Murakami, J. Chromatogr.178, 393 (1979).

    Article  CAS  Google Scholar 

  31. P. Dufek, J. Chromatogr.281, 49 (1983).

    Article  CAS  Google Scholar 

  32. X. Geng, F. E. Regnier, J. Chromatogr.332, 147 (1985).

    Article  CAS  Google Scholar 

  33. J. Zhao, Y. Xu, X. Geng, Xibei Daxue Xuebao, Ziran Kexueban16, 25 (1986).

    CAS  Google Scholar 

  34. X. Geng, F. E. Regnier, J. Chromatogr.296, 15 (1984).

    CAS  Google Scholar 

  35. S. Wu, K. Benedek, B. L. Karger, J. Chromatogr.359, 3 (1986).

    Article  CAS  Google Scholar 

  36. M. Kunitani, D. Johnson, L. R. Snyder, J. Chromatogr.371, 313 (1986).

    Article  CAS  Google Scholar 

  37. Y. Ohtsu, H. Fukui, T. Kanda, N. Nakamura, M. Nakao, O. Nakata, F. Fujiyama, Chromatographia24, 380 (1980).

    Google Scholar 

  38. N. E. Tayar, H. V. D. Waterbeemd, B. Testa, J. Chromatogr.320, 293 (1985).

    Google Scholar 

  39. L. C. Sander, S. A. Wise, Anal. Chem.61, 1747 (1989).

    Article  Google Scholar 

  40. M. C. Hennion, R. Rosset, Chromatographia25, 43 (1988).

    Article  CAS  Google Scholar 

  41. J. W. Dolan, J. R. Gant, L. R. Snyder, J. Chromatogr.165, 31 (1979).

    Article  CAS  Google Scholar 

  42. W. E. Hammers, G. J. Meurs, C. L. De Ligny, J. Chromatogr.247, 1 (1982).

    Article  CAS  Google Scholar 

  43. A. Opperhuizen, T. L. Sinnige, J. M. D. Van der Steen, O. Hutzinger, J. Chromatogr.388, 51 (1987).

    Article  CAS  Google Scholar 

  44. R. Hermann, J. Phys. Chem.76, 2754 (1972).

    Article  CAS  Google Scholar 

  45. G. Amidon, S. Yalkowsky, S. Leung, J. Pharm. Sci.63, 1858 (1974).

    CAS  Google Scholar 

  46. C. Horvath, W. Melander, I. Molnar, J. Chromatogr.125, 129 (1976).

    CAS  Google Scholar 

  47. F. Franks, Faraday Symp. Chem. Soc.17, 11 (1982).

    Article  Google Scholar 

  48. A. Leo, C. Hansch, P. Y. C. Jow, J. Med. Chem.19, 611 (1976).

    Article  CAS  Google Scholar 

  49. R. T. Buckler, J. Med. Chem.15, 578 (1972).

    Article  CAS  Google Scholar 

  50. T. Fujita, T. Nishioka, M. Nakajima, J. Med. Chem.20, 1071 (1977).

    Article  CAS  Google Scholar 

  51. K. Miyake, N. Mizuno, H. Terada, J. Chromatogr.439, 227 (1988).

    Article  CAS  Google Scholar 

  52. M. J. Kamlet, R. M. Doherty, M. H. Abraham, Y. Marcus, R. W. Taft, J. Phys. Chem.92, 5244 (1988).

    Article  CAS  Google Scholar 

  53. M. J. Kamlet, J.-L. M. Abboud, M. H. Abraham, R. W. Taft, J. Org. Chem.48, 2877 (1983).

    Article  CAS  Google Scholar 

  54. R. F. Rekker, “The Hydrophobic Fragmental Constant”, Elsevier, Amsterdam (1977).

    Google Scholar 

  55. K. Karch, I. Sebestian, I. Halasz, J. Chromatogr.122, 3 (1976).

    CAS  Google Scholar 

  56. A. Kaibara, M. Hirose, T. Nakagawa, Chromatographia, submitted.

  57. A. Kaibara, C. Hohda, N. Hirata, T. Nakagawa, J. Chromatogr. Sci.27, 716 (1989).

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kaibara, A., Hohda, C., Hirata, N. et al. Evaluation of solute hydrophobicity by reversed-phase high performance liquid chromatography using aqueous binary mobile phases. Chromatographia 29, 275–288 (1990). https://doi.org/10.1007/BF02317918

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02317918

Key Words

Navigation