The reserved-phase HPLC study of the complexation of 5,17-bis-(N-tolylimino-methyl)-25,27-dipropoxycalix[4]arene with aromatic carboxylic acids

Authors

  • O. I. Kalchenko Institute of Organic Chemistry of the NAS of Ukraine, Ukraine
  • A. V. Solovyov University of California, United States
  • V. I. Kalchenko Institute of Organic Chemistry of the NAS of Ukraine, Ukraine

DOI:

https://doi.org/10.24959/ophcj.15.856

Keywords:

Calix[4]arene, reversed-phase high performance liquid chromatography, aromatic carboxylic acids, molecular modelling, Host-Guest complexation

Abstract

The Host-Guest complexation of 5,17-bis-(N-tolyliminomethyl)-25,27-dipropoxycalix[4]arene with a number of aromatic carboxylic acids has been studied by reversed-phase high-performance liquid chromatography. The mobile phase was acetonitrile-water (80/20, v/v) with addition of 0.1% formic acid. The column was LiChrosorb RP 18, the UV detector operated at λ = 254 nm and at 26°C. The main chromatographic characteristics (retention time t[sub]R[/sub] and capacity factor k’) of the aromatic carboxylic acids have been determined. The lipophilicity values of log P of carboxylic acids, as well as the binding constants K[sub]A[/sub] (387-941 M[sup]-1[/sup]) and Gibbs free energies ∆G (-14.74 – -16.94 kJ/mol) of the calixarene complexes with aromatic carboxylic acids have been calculated. The molecular modelling (Hyper Chem, version 8.0) of the calixarene complexes has revealed the presence of hydrogen bonds between carboxylic groups of the acids and nitrogen atoms of imino groups at the upper rim or oxygen atoms of hydroxyl groups at the lower rim of the calixarene macrocycle. The infl uence of log P lipophilicity of acids on K[sub]A[/sub] values of the calixarene complexes has been assessed. The linear dependence of the binding constants on the acid lipophilicity indicates a signifi cant role of solvophobic interactions on the complexation process. The relationship between supramolecular (K[sub]A[/sub]) and physicochemical (molecular weight, log P, pKa) characteristics of acids has been found. The binding constants K[sub]A[/sub] of the complexes increase with increase of their molecular weight and log P values.

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References

  1. Ludwig R. Microchimica Acta, 2005, Vol. 152, pp.1-19.
  2. Menon K., Sewani M. Reviews in Analytical Chemistry, 2006. Vol. 25, pp.49-82.
  3. Mutihac L., Buschmann H. J. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 2005, Vol. 51(1), pp.53-57.
  4. De Fátima A., Fernandes S. A., Sabino A. A. Current Drug Discovery Technologies, 2009, Vol. 6, pp.151-170.
  5. Rodik R. V., Boyko V. I., Kalchenko V. I. Current Medicinal Chemistry, 2009. Vol. 16, pp.1630-1655.
  6. Cherenok S., Kalchenko V. Topic Heterocycl. Chemistry, 2009, Vol. 20, pp.229-273.
  7. Sansone F., Baldini L., Casnati A., Ungaro R. New Journal of Chemistry, 2010, Vol. 34, pp.2715-2728.
  8. Gutsche C. D. Calixarenes: Introduction, Monographs in Supramolecular Chemistry, Cambridge, The Royal Society of Chemistry, 2008.
  9. Asfari Z., Boehmer V., Harowfield J., Vicens J. (Eds.). Calixarenes 2001, Dordrecht, Kluwer Academic, 2001.
  10. Böhmer V. Angewandte Chemie International Edition, 1995, Vol. 34, pp.713-745.
  11. Diamond D., Nolan K. Analytical Chemistry, 2001, Vol. 73, pp.22ª-29A.
  12. Da Silva E., Lazar A. N., Coleman A. W. Journal of Drug Delivery Science and Technology, 2004, Vol. 14. pp.3-20.
  13. Perret F., Lazar A. N., Coleman A. W. Chemical Communications, 2006, pp.2425-2438.
  14. Sansone F., Segura, M., Ungaro, R. Calixarenes in bioorganic and biomimetic chemistry. In: Calixarenes 2001, Asfari M.-Z., Böhmer V., Harrowfield J., Vicens J. (eds.), Kluwer Academic Publishers, Dordrecht, 2001, pp.496-512.
  15. Coleman A. W., Perret F., Moussa M., Dupin M., Guo Y., Perron H. Topics in Curreent Chemistry, 2007, Vol. 277, pp.31-88.
  16. Zadmard R., Schrader T. Journal of American Chemical Society, 2005, Vol. 127, pp.904-915.
  17. Mutihac L., Lee J. H., Kim J. S., Vicens J. Chemical Society Reviews, 2011, Vol. 40, pp.2777-2796.
  18. Jaganathan S. K., Supriyanto E., Mandal M. World Journal of Gastroenterol, 2013, Vol.19, pp.7726-7734.
  19. Strandås C., Kamal-Eldin A., Andersson R., Åman P. Food Chemistry, 2008, Vol. 110, pp.997-999.
  20. Ferguson L. R., Zhu S., Harris P. J. Molecular Nutrition and Food Research, 2005, Vol. 49, pp.585-693.
  21. Kikugawa K., Hakamada T., Hasunuma M., Kurechi T. Journal of Agricultural and Food Chemistry, 1983, Vol. 4, pp.780-785.
  22. Budavari S. (ed) An Encyclopedia of Chemicals, Drugs, and Biologicals (12th ed.), Whitehouse Station, New Jersey, Merck, ISBN 0911910123, 1996.
  23. Johnsen U. E., Jacobson C. R., Laforge R. A., Hanna C. Journal of Pharmaceutical Science, 1962, Vol. 51, pp.799-801.
  24. Rao C. V., Desai D., Rivenson A., Simi B., Amin S., Reddy B. S. Cancer research, Vol. 55, 1995, pp.2310-2315.
  25. Kalchenko O. I., Lipkowski J., Kalchenko V. I., Vysotsky M. A., Markovsky L. N. Journal of Chromatographic Science, 1998, Vol. 36, pp.269-273.
  26. Hansch C., Leo A., Hoekman D. H. Exploring QSAR: Hydrophobic, Electronic, and Steric Constants (ACS Professional Reference Book) American Chemical Society, Medical, 1995.
  27. http://www.hyper.com/Download/AllDownloads/tabid/470/Default.aspx.
  28. Kalchenko O. I., Cherenok S. A., Kalchenko V. I., Solovyov A. V., Gorbatchuk V. V. Journal of Organic and Pharmaceutical Chemistry, 2013, Vol. 11, pp.3-8.
  29. Lipkowski J., Kalchenko O. I., Slowikowska J., Kаlchеnkо V. I., Lukin O. V., Markovsky L. N., Nowakowski R. Journal of Physical and Organic Chemistry, 1998, Vol. 11, pp.426-435.

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Published

2015-09-10

How to Cite

(1)
Kalchenko, O. I.; Solovyov, A. V.; Kalchenko, V. I. The Reserved-Phase HPLC Study of the Complexation of 5,17-Bis-(N-Tolylimino-Methyl)-25,27-dipropoxycalix[4]arene With Aromatic Carboxylic Acids. J. Org. Pharm. Chem. 2015, 13, 3-8.

Issue

Vol. 13 No. 3(51) (2015)

Section

Original Researches

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