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Solvent Effect on the Gibbs Energy of Proton Transfer in the 2,6-Dichlorophenol-Triethylamine Complex

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Abstract

Using dipole moment measurements, the Gibbs energy ΔGPT of proton transfer in the complex of 2,6-dichlorophenol with triethylamine was determined in different solvents. The effect of solvent on ΔGPT was quantitatively discussed in terms of reaction field models for homogeneous and heterogeneous dielectric media. The specific complex–solvent interactions which, in addition to electrostatic interaction, stabilize the PT polar form of the complex is discussed as a function of the empirical parameters describing the polar and hydrogen-donating (electron-accepting) properties of the solvent.

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REFERENCES

  1. G. S. Denisov, A. I. Kulbida, V. A. Micheev, I. G. Rumynskaja, and V. M. Schreiber, J. Mol. Liquid 26, 159 (1983).

    Google Scholar 

  2. J. L. Andres, M. Duran, A. Lledos, and J. Bertran, Chem. Phys. Lett. 124, 177 (1986).

    Google Scholar 

  3. J. Juanos i Timoneda and J. T. Hynes, J. Phys. Chem. 95, 10431 (1991).

    Google Scholar 

  4. S. G. Christov, Chem. Phys. 168, 327 (1992).

    Google Scholar 

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

    Google Scholar 

  6. J. Malecki and J. Jadżyn, Acta Phys. Polon. 40, 599 (1972).

    Google Scholar 

  7. D. Eustace and E. Grunwald, J. Amer. Chem. Soc. 96, 7171 (1974).

    Google Scholar 

  8. I. Majerz, Z. Malarski, and L. Sobczyk, Bull. Soc. Chim. Belg. 91, 605 (1982).

    Google Scholar 

  9. J. Fritsch and G. Zundel, J. Phys. Chem. 85, 556 (1981).

    Google Scholar 

  10. G. Zundel and J. Fritsch, J. Phys. Chem. 88, 6295 (1984).

    Google Scholar 

  11. R. Kramer and G. Zundel, Z. Phys. Chem. [NF], 144, 265 (1985).

    Google Scholar 

  12. W. A. Millen and D. W. Watts, J. Amer. Chem. Soc. 89, 6051 (1967).

    Google Scholar 

  13. J.-L. M. Abboud and R. W. Taft, J. Phys. Chem. 83, 412 (1979).

    Google Scholar 

  14. O. Tapia, in Molecular Interactions, Vol. 3, Chap. 2. H. Ratajczak and W. J. Orville-Thomas, eds. (Wiley, New York, 1982).

    Google Scholar 

  15. A. Raudino, F. Zuccarello, and G. Buemi, Chem. Phys. 112, 77 (1987).

    Google Scholar 

  16. T. Kakitani and N. Mataga, Chem. Phys. Lett. 124, 437 (1986).

    Google Scholar 

  17. Y. Hatano, T. Kakitani, A. Yoshimori, M. Saito, and N. Mataga, J. Phys. Soc. Jpn. 59, 1104 (1990).

    Google Scholar 

  18. Z. Pawelka, J. Mol. Struct. 172, 15 (1988); J. Mol. Struct. 178, 161 (1988).

    Google Scholar 

  19. Z. Pawelka, Bull. Polon. Acad. Sci. Chem. 36, 69 (1988).

    Google Scholar 

  20. H. Block and S. M. Walker, Chem. Phys. Lett. 19, 363 (1973).

    Google Scholar 

  21. D. L. Beveridge and G. W. Schnuelle, J. Phys. Chem. 79, 2562 (1975).

    Google Scholar 

  22. Z. Pawelka and L. Sobczyk, Rocz. Chem. 49, 1383 (1975).

    Google Scholar 

  23. R. Lindemann and G. Zundel, J. Chem. Soc. Faraday Trans. 2 73, 788 (1977).

    Google Scholar 

  24. R. Kramer and G. Zundel, J. Chem. Soc. Faraday Trans. 86, 301 (1990).

    Google Scholar 

  25. T. Kuc, Z. Pawelka, and L. Sobczyk, Phys. Chem. Chem. Phys. 2, 211 (2000).

    Google Scholar 

  26. A. Weissberger, E. S. Praskauer, J. A. Riddick, and E. E. Toops, Technique of Organic Chemistry, Vol. VII, Organic Solvents (Wiley (Interscience), New York, 1955).

    Google Scholar 

  27. V. S. Pilyugin, S. V. Vasin, and T. A. Maslova, Zh. Obsh. Khim. 51, 1460 (1981).

    Google Scholar 

  28. L. Onsager, J. Amer. Chem. Soc. 58, 1486 (1936).

    Google Scholar 

  29. Z. Pawelka, J. Chem. Soc. Faraday Trans. 2 84, 1683 (1988).

    Google Scholar 

  30. V. S. Pilyugin, S. V. Vasin, and V. V. Zinovev, Zh. Fiz. Khim. 58, 937 (1984).

    Google Scholar 

  31. M. Rospenk and Th. Zeegers-Huyskens, J. Phys. Chem. 101, 8428 (1997).

    Google Scholar 

  32. R. Nouwen and P. Huyskens, J. Mol. Struct. 16, 459 (1973).

    Google Scholar 

  33. J. P. Hawranek, J. Oszust, and L. Sobczyk, J. Phys. Chem. 76, 2112 (1972).

    Google Scholar 

  34. H. Ratajczak and L. Sobczyk, Bull. Acad. Polon. Sci. Ser. Sci. Chim. 28, 93 (1970).

    Google Scholar 

  35. C. J. F. Bottcher, Theory of Electric Polarization (Elsevier, Amsterdam, 1973).

    Google Scholar 

  36. R. J. Abraham and I. M. Siverns, J. Chem. Soc. Perkin II, p. 1586 (1972).

    Google Scholar 

  37. L. Dosen-Micovic and N. L. Allinger, Tetrahedron 34, 3385 (1978).

    Google Scholar 

  38. Y. Marcus, Chem. Soc. Rev. 22, 409 (1993).

    Google Scholar 

  39. K. Dimroth, Ch. Reichardt, T. Siepmann, and F. Bohlmann, Liebigs Ann. Chem. 661, 1 (1966).

    Google Scholar 

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

    Google Scholar 

  41. C. G. Swain, M. S. Swain, A. L. Powell, and S. Alunni, J. Amer. Chem. Soc. 105, 502 (1983).

    Google Scholar 

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  1. Faculty of Chemistry, University of Wroc#38;;aw, F. Joliot-Curie 14, 50-383, Wroc#38;;aw, Poland

    T. Kuc & Z. Pawe#38;;ka

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  1. T. Kuc
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  2. Z. Pawe#38;;ka
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Kuc, T., Pawe#38;;ka, Z. Solvent Effect on the Gibbs Energy of Proton Transfer in the 2,6-Dichlorophenol-Triethylamine Complex. Journal of Solution Chemistry 30, 375–387 (2001). https://doi.org/10.1023/A:1010331307822

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