QSPR Models for Chromatographic Retention of Some Azoles with Physicochemical Properties

  • Polyakova, Yulia ;
  • Jin, Long Mei ;
  • Row, Kyung-Ho
  • Published : 2006.02.20


This work deals with 24 substances composed of nitrogen-containing heterocycles. The relationships between the chromatographic retention factor (k) and those physicochemical properties which are relevant in quantitative structure-properties relationship (QSPR) studies, such as the polarizability $(\alpha)$, molar refractivity (MR), lipophilicity (logP), dipole moment $(\mu)$, total energy $(E_{tot})$, heat of formation $(\Delta H_f)$, molecular surface area $(S_M)$, and binding energy $(E_b)$, were investigated. The accuracy of the simple linear regressions between the chromatographic retention and the descriptors for all of the compounds was satisfactory (correlation coefficient, $0.8 \leq r \leq 1.0$). The QSPR models of these nitrogen-containing heterocyclic compounds could be predicted with a multiple linear regression equation having the statistical index, r = 1.000. This work demonstrated the successful application of the multiple linear approaches through the development of accurate predictive equations for retention factors in liquid chromatography.


Nitrogen-containing heterocycles;Retention factor;QSPR;Correlation


  1. Csizmadia, I. G. Theory and Practice of MO Calculations on Organic Molecules; Elsevier: Amsterdam, 1976
  2. Bodor, M.; Gabanyi, Z.; Wong, C.-K. J. Am. Chem. Soc. 1989, 111, 3783
  3. Karelson, M. Molecular Descriptors in QSAR/QSPR; J. Wiley & Sons: New York, 2000
  4. Wang, R.; Gao, Y.; Lai, L. Perspect. Drug Discov. Des. 2000, 19, 47
  5. Bruket, U.; Allinger, N. L. Molecular Mechanics; ACS Monograph, American Chemical Society: Washington, 1982
  6. Palm, V. A. Fundaments in Quantitative Theory of Organic Chemistry; Khimiya: Russia (in Russian), 1967
  7. Kubinyi, H.; In QSAR: Hansch Analysis and Related Approaches; Mannhold, R.; Krogs Gaard-Larsen, P.; Timmerman, H., Eds.; VCH: Weinheim, 1993
  8. Gami-Yilinkou, G.; Kaliszan, R. J. Chromatogr. 1991, 550, 573
  9. Dai, J.; Jin, L.; Yao, S.; Wang, L. Chemosphere 2001, 42(8), 899
  10. Breneman, C. M.; Rhem, M. J. Comput. Chem. 1997, 18, 182<182::AID-JCC4>3.0.CO;2-R
  11. Kaliszan, R. Quantitative Structure-Chromatographic Retention Relationships; Wiley: New York, 1987
  12. Feng, Y.; Zhu, P.; Hu, Z. J. Chromatogr. 1988, 25, 382
  13. Feng, Y. Q.; Liu, M. C.; Hu, Z. Chin. J. Chromatogr. 1986, 4, 259
  14. Hinze, W. L.; Weber, S. G. Anal. Chem. 1991, 63, 1808
  15. Yamagami, C.; Oguda, T.; Takao, N. J. Chromatogr. 1990, 514, 123
  16. Smith, R. M. J. Chromatogr. A 1993, 656, 381
  17. Law, B.; Weir, S. J. Chromatogr. A 1993, 657, 17
  18. Smith, P. L.; Cooper, W. T. Chromatographia 1988, 25, 55
  19. Billiet, H. A. H.; Schoenmakers, P. J.; Galan, L. D. J. Chromatogr. 1981, 218, 443
  20. Kleeman, A.; Engel, J.; Kutscher, B.; Reichert, D. Pharmaceutical Substances, 3rd ed.; Stuttgart: New York, 1999
  21. Todeschini, R.; Consonni, V. Handbook of Molecular Descriptors; Wiley-VCH: Weinheim (Germany), 2000
  22. Atkins, P. W. Quanta; Oxford University Press: Oxford, 1991
  23. Hansch, C.; Leo, A. J. Substituent Constants for Correlation Analysis in Chemistry and Biology; John Wiley: New York, 1979
  24. Leo, A. J. Chem. Rev. 1993, 93, 1281
  25. Townsend, L. B. Chem. Rev. 1976, 67, 533
  26. Kaibara, A.; Hohda, C.; Hirata, N.; Hirose, M.; Nakagawa, T. Chromatographia 1990, 29, 275
  27. Roca, R. M. S.; Albarez, F. J. G. J. Chromatogr. 1992, 607, 91
  28. Sanghvi, T. QSAR & Combinatorial Science 2003, 22, 258
  29. Diaz-Calleja, R.; Riande, E., In Dielectric Spectroscopy of Polymeric Materials; Runt, J. P.; Fitzgerald, J. J., Eds.; American Chemical Society: Washington, DC, 1997; pp 139-173

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