Skip to main content
Log in

Solvent effect in hydrogen-bond formation betweenp-nitrophenol and amines

  • Published:
Journal of Solution Chemistry Aims and scope Submit manuscript

Abstract

Thermodynamic characteristics for the 1:1 complex formation reactions ofp-nitrophenol with amines in benzene, chlorobenzene, ando-dichlorobenzene have been derived from combined spectrophotometric equilibrium constant determinations and calorimetric measurements. For cyclohexane as the reaction medium, approximate values of the reaction heats have been calculated from temperature dependences of the equilibrium constants. The results are analyzed in terms of the separately determined heats of transfer of the reactants between the solvents used. Usingp-nitrophenol andp-fluoronitrobenzene as reference compounds, the hydrogen-bond-type interactions ofp-nitrophenol with the aromatic solvents are shown to be accompanied by other specific interactions of comparable strength.

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. L. Bell and G. M. Barrow,J. Chem. Phys. 31, 1158 (1959).

    Google Scholar 

  2. T. Gramstad,Acta Chim. Scand. 16, 807 (1962).

    Google Scholar 

  3. R. Scott, D. DePalma, and S. Vinogradov,J. Phys. Chem. 72, 3192 (1968).

    Google Scholar 

  4. R. Scott and S. Vinogradov,J. Phys. Chem. 73, 1890 (1969).

    Google Scholar 

  5. H. Baba, A. Matsuyama, and K. Kokubun,Spectrochim. Acta, Part A 25, 1709 (1969).

    Google Scholar 

  6. R. A. Hudson, R. M. Scott, and S. N. Vinogradov,J. Phys. Chem. 76, 1986 (1972).

    Google Scholar 

  7. M. S. Nozari and R. S. Drago,J. Am. Chem. Soc. 94, 6877 (1972).

    Google Scholar 

  8. E. M. Arnett, E. J. Mitchell, and T. S. S. R. Murty,J. Am. Chem. Soc. 96, 3875 (1974).

    Google Scholar 

  9. J. N. Spencer, R. S. Harner, and C. D. Penturelli,J. Phys. Chem. 19, 2488 (1975).

    Google Scholar 

  10. Z. Pawełka and L. Sobczyk,Rocz. Chem. 19, 1383 (1975).

    Google Scholar 

  11. J. N. Spencer, J. R. Sweigart, M. E. Brown, R. L. Bensing, T. L. Hassinger, W. Kelly, D. L. Housel, and G. W. Reisinger,J. Phys. Chem. 80, 811 (1976).

    Google Scholar 

  12. W. Libuś and W. Moska,Bull. Acad. Pol. Sci., Ser. Sci. Chim. 17, 669 (1969);17, 375 (1969);20, 897 (1972).

    Google Scholar 

  13. E. M. Woolley and L. G. Hepler,J. Phys. Chem. 76, 3058 (1972).

    Google Scholar 

  14. D. Bloser, J. Murphy, and J. N. Spencer,Can. J. Chem. 49, 3913 (1971).

    Google Scholar 

  15. E. Weissberger, Organic Solvents (Interscience Publishers, New York, 1955).

    Google Scholar 

  16. N. J. Rose and R. S. Drago,J. Am. Chem. Soc. 81, 6138 (1959).

    Google Scholar 

  17. M. Mecik and W. Libuś,Bull. Acad. Pol. Sci., Ser. Sci. Chim.,24, 477 (1976).

    Google Scholar 

  18. E. M. Wooley, J. G. Travers, B. P. Erno, and L. G. Hepler,J. Phys. Chem. 75, 3591 (1971).

    Google Scholar 

  19. J. S. Coleman, L. P. Varga, and S. H. Mastin,Inorg. Chem. 9, 1019 (1970).

    Google Scholar 

  20. R. A. Hudson, R. M. Scott, and S. N. Vinogradov,Spectrochim. Acta, Part A 26, 337 (1970).

    Google Scholar 

  21. W. Libuś, Z. Dauter, and W. Moska,Bull. Acad. Pol. Sci., Ser. Sci. Chim. 21, 593 (1973).

    Google Scholar 

  22. E. S. Thomsen,Acta Chim. Scand. 26, 2100 (1972).

    Google Scholar 

  23. A. Abe and P. J. Flory,J. Am. Chem. Soc. 87, 1838 (1965).

    Google Scholar 

  24. D. H. Andrew, G. Lynn, and J. Johnson,J. Am. Chem. Soc. 48, 1284 (1926).

    Google Scholar 

  25. Beilsteins Handbuch der Organischen Chemie, Vol. V, (Springer, Berlin, 1930), p. 111.

  26. R. D. Kross and V. A. Fassel,J. Am. Chem. Soc. 78, 4225 (1956).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Libuś, W., Mecik, M. & Sułek, W. Solvent effect in hydrogen-bond formation betweenp-nitrophenol and amines. J Solution Chem 6, 865–879 (1977). https://doi.org/10.1007/BF00648075

Download citation

  • Received:

  • Revised:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00648075

Key words

Navigation