Skip to main content
SpringerLink
Log in

Thermodynamics of the hydrogen bonding of nitrogen-containing cyclic and aromatic compounds with proton donors: The structure-property relationship

  • Chemical Thermodynamics and Thermochemistry
  • Published:
Russian Journal of Physical Chemistry A Aims and scope Submit manuscript

Abstract

Enthalpies of dissolution are measured at infinite dilution of nitrogen-containing cyclic (pyrrolidine, piperidine) and aromatic compounds (aniline, N-methylaniline, N,N-dimethylaniline, N-methylimidazole, pyridine, 2-, 3-, 4-methylpyridine, pyrrole, N-methylpyrrole) in chloroform and dichloromethane, and vice versa (T = 298.15 K). The enthalpies of hydrogen bonds in the above systems are calculated. Relationships between resulting thermochemical data and the structure of nitrogen-containing cyclic and aromatic compounds are explored.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. F. Delgado-Vargas, A. Jiménez, and O. Paredes-López, Crit. Rev. Food Sci. Nutrit. 40, 173 (2000).

    Article  CAS  Google Scholar 

  2. E. Atlas, L. Fishbein, et al., Antropogenic Compounds, The Handbook of Environmental Chemistry, Vol. 3, Part C (Spinger, 1984), p. 1.

    Book  Google Scholar 

  3. A. F. Pozharskii, A. Soldatenkov, and A. R. Katritzky, Heterocycles in Life and Society: An Introduction to Heterocyclic Chemistry, Biochemistry, and Applications, 2nd ed. (Wiley, 2011).

    Book  Google Scholar 

  4. C. Chiappe and D. Pieraccini, J. Phys. Org. Chem. 18, 275 (2005).

    Article  CAS  Google Scholar 

  5. N. M. Luscombe, R. A. Laskowski, and J. M. Thornton, Nucl. Acid Res. 29, 2860 (2001).

    Article  CAS  Google Scholar 

  6. G. A. Jeffrey and W. Saenger, Hydrogen Bonding in Biological Structures (Springer, Berlin, 1991).

    Book  Google Scholar 

  7. J. A. Joule and K. Mills, Heterocyclic Chemistry, 5th ed. (Wiley, 2010).

    Google Scholar 

  8. A. Gomez-Zavaglia and R. Fausto, J. Phys. Chem. A 108, 6953 (2004).

    Article  CAS  Google Scholar 

  9. I. Dauster, C. A. Rice, P. Zielke, and M. A. Suhm, Phys. Chem. Chem. Phys. 10, 2827 (2008).

    Article  CAS  Google Scholar 

  10. V. E. Borisenko, Y. A. Zavjalova, T. G. Tretjakova, et al., J. Mol. Liq. 109, 125 (2004).

    Article  CAS  Google Scholar 

  11. S. Yamaguchi, M. Banno, K. Ohta, and K. Tominaga, J. Phys. Chem. A 117, 6323 (2013).

    Article  CAS  Google Scholar 

  12. J. H. Lady and K. B. Whetsel, J. Phys. Chem. 71, 1421 (1967).

    Article  CAS  Google Scholar 

  13. Y. Matsumoto and K. Honma, J. Chem. Phys. 130, 054311 (2009).

    Article  Google Scholar 

  14. A. Kumar, M. Kolaski, and K. S. Kim, J. Chem. Phys. 128, 034304 (2008).

    Article  Google Scholar 

  15. S. Bhattacharya, M. Banerjee, and A. K. Mukherjee, Spectrochim. Acta A 57, 2409 (2001).

    Article  CAS  Google Scholar 

  16. S. Muzaffar and A. Andrabi, Ind. J. Chem. 41, 2306 (2002).

    Google Scholar 

  17. J. S. Lomas and F. Maurel, J. Phys. Org. Chem. 21, 464 (2008).

    Article  CAS  Google Scholar 

  18. L. C. Ducati, C. B. Braga, R. Rittner, and C. F. Tormena, Spectrochim. Acta A 116, 196 (2013).

    Article  CAS  Google Scholar 

  19. J. N. Spencer, J. E. Gleim, C. H. Blevlns, et al., J. Phys. Chem. 83, 1249 (1979).

    Article  CAS  Google Scholar 

  20. W. Marczak, A. Heintz, and M. Bucek, J. Chem. Thermodyn. 36, 575 (2004).

    Article  CAS  Google Scholar 

  21. J. N. Spencer, J. E. Gleim, C. H. Blevins, et al., J. Phys. Chem. 83, 2615 (1979).

    Article  CAS  Google Scholar 

  22. K. V. Zaitseva, M. A. Varfolomeev, and B. N. Solomonov, Thermochim. Acta 535, 8 (2012).

    Article  CAS  Google Scholar 

  23. B. N. Solomonov, M. A. Varfolomeev, and V. B. Novikov, J. Phys. Chem. 19, 263 (2006).

    CAS  Google Scholar 

  24. K. V. Zaitseva, M. A. Varfolomeev, and B. N. Solomonov, Russ. J. Gen. Chem. 82, 1669 (2012).

    Article  CAS  Google Scholar 

  25. A. Wilson, A. Tian, and N. Dabadge, Struct. Chem., No. 6, 1841 (2013).

    Google Scholar 

  26. I. A. Kuz’mina, V. A. Sharnin, M. A. Volkova, and K. A. Sitnikova, Russ. J. Phys. Chem. A 87, 2020 (2013).

    Article  Google Scholar 

  27. D. D. Perrin, W. L. F. Armarego, and D. R. Perrin, Purification of Laboratory Chemicals, 2nd ed. (Pergamon, Oxford, 1980).

    Google Scholar 

  28. K. V. Zaitseva, M. A. Varfolomeev, V. B. Novikov, and B. N. Solomonov, J. Chem. Thermodyn. 43, 1083 (2011).

    Article  CAS  Google Scholar 

  29. R. Sabbah, X. W. An, J. S. Chikos, et al., Thermochim. Acta 331, 93 (1999).

    Article  CAS  Google Scholar 

  30. B. N. Solomonov, V. B. Novikov, M. A. Varfolomeev, and N. M. Mileshko, J. Phys. Org. Chem. 18, 49 (2005).

    Article  CAS  Google Scholar 

  31. M. H. Abraham, Chromatografia 23, 243 (1987).

    Article  CAS  Google Scholar 

  32. C. Mintz, T. Ladlie, K. Burton, et al., QSAR Comb. Sci. 27, 627 (2008).

    Article  CAS  Google Scholar 

  33. J. Catalan, J. Gomez, L. Saiz, et al., J. Chem. Soc., Perkin Trans. II 12, 2301 (1995).

    Article  Google Scholar 

  34. V. B. Novikov, D. I. Abaidullina, N. Z. Gainutdinova, et al., Russ. J. Phys. Chem. A 80, 1790 (2006).

    Article  CAS  Google Scholar 

  35. M. Joesten and L. Shaad, Hydrogen Bonding (Marcel Dekker, New York, 1974), p. 622.

    Google Scholar 

  36. W. C. Duer and G. L. Bertrand, J. Am. Chem. Soc. 96, 1300 (1974).

    Article  CAS  Google Scholar 

  37. D. M. Trampe and C. A. Eckert, J. Chem. Eng. Data 36, 112 (1991).

    Article  CAS  Google Scholar 

  38. K. V. Zaitseva, M. A. Varfolomeev, and B. N. Solomonov, J. Mol. Struct. 1018, 14 (2012).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Butlerov Institute of Chemistry, Kazan Federal University, Kazan, 420008, Russia

    I. T. Rakipov, M. A. Varfolomeev, A. Yu. Kirgizov & B. N. Solomonov

Authors
  1. I. T. Rakipov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. M. A. Varfolomeev
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. Yu. Kirgizov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. B. N. Solomonov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to M. A. Varfolomeev.

Additional information

Original Russian Text © I.T. Rakipov, M.A. Varfolomeev, A.Yu. Kirgizov, B.N. Solomonov, 2014, published in Zhurnal Fizicheskoi Khimii, 2014, Vol. 88, No. 12, pp. 1861–1867.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Rakipov, I.T., Varfolomeev, M.A., Kirgizov, A.Y. et al. Thermodynamics of the hydrogen bonding of nitrogen-containing cyclic and aromatic compounds with proton donors: The structure-property relationship. Russ. J. Phys. Chem. 88, 2023–2028 (2014). https://doi.org/10.1134/S0036024414120255

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S0036024414120255

Keywords

Search

Navigation