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Theoretical and Experimental Chemistry

, Volume 4, Issue 3, pp 247–249 | Cite as

Effects of a para-substituent in di-o-t-butylphenol on association with t-butanol

  • V. D. Pokhodenko
  • V. S. Kuts
Article

Abstract

NMR studies reveal a linear correlation between the chemical shift for the OH proton in the phenol and the Hammett σ for the substituent. The degree of association with t-butanol increases with the electron-acceptor affinity of the substituent. There is no fast exchange between the OH groups of the phenol and the alcohol; this is confirmed by SCF and Hückel calculations.

Keywords

Alcohol Phenol Chemical Shift Linear Correlation Fast Exchange 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

  1. 1.
    W. C. Sears and L. I. Kitchen, J. Am. Chem. Soc., 71, 4110, 1949.Google Scholar
  2. 2.
    K. U. Ingold, Canad. J. Chem., 38, 1092, 1960.Google Scholar
  3. 3.
    N. A. Puttnan, J. Chem. Soc., 486, 5100, 1960.Google Scholar
  4. 4.
    J. Yamaguchi, Bull. chem. Soc. Japan, 34, 451, 1961.Google Scholar
  5. 5.
    V. F. Bystrov, collection: The Hydrogen Bond [in Russian], Nauka, Moscow, 1964.Google Scholar
  6. 6.
    J. J. Wren and P. M. Lenthen, J. Chem. Soc., 2557, 1961.Google Scholar
  7. 7.
    L. J. Bellamy, G. Eglinton, and J. F. Morman, J. Chem. Soc., 4762, 1961.Google Scholar
  8. 8.
    B. J. Somers and H. S. Gutowsky, J. Am. Chem. Soc., 85, 3065, 1963.Google Scholar
  9. 9.
    V. A. Pal'm, Usp. Khim., 30, 1069, 1961.Google Scholar
  10. 10.
    U. H. Jaffe, Chem. Revs., 53, 191, 1953.Google Scholar
  11. 11.
    A. I. Brodskii, Izv. AN SSSR, OKhN, 3, 1949; DAN SSSR, 93, 847, 1953.Google Scholar
  12. 12.
    A. I. Brodskii, ZhOKh, 24, 413, 1954.Google Scholar
  13. 13.
    V. V. Ershov, A. A. Volod'kin, and G. N. Bogdanov, Usp. Khim., 32, 154, 1963.Google Scholar
  14. 14.
    R. Pariser and R. G. Parr, J. Chem. Phys., 21, 466, 767, 1953.Google Scholar
  15. 15.
    T. A. Pople, Trans. Faraday Soc., 49, 1375, 1953.Google Scholar
  16. 16.
    A. Streitweiser, Molecular Orbital Theory for Organic Chemists [Russian translation), Mir, Moscow, 1965.Google Scholar
  17. 17.
    V. A. Kuprievich, V. I. Danilov, and O. V. Shramko, TEKh [Theoretical and Experimental Chemistry], 2, 734, 1966.Google Scholar
  18. 18.
    B. P. Pullman and A. P. Pullman, Quantum Biochemistry [Russian translation], Mir, Moscow, 1965.Google Scholar
  19. 19.
    N. Mataga and K. Nischimoto, Z. phys. Chem., N. F., 13, 140, 1957.Google Scholar
  20. 20.
    K. Ohno, Theoret. chim. Acta, 2, 219, 1964.Google Scholar
  21. 21.
    G. G. Dyadyusha and V. A. Kuprievich, TEKh [Theoretical and Experimental Chemistry], 1, 840, 1965.Google Scholar
  22. 22.
    Yu. A. Kruglyak, TEKh [Theoretical and Experimental Chemistry], 1, 418, 1965.Google Scholar
  23. 23.
    Yu. A. Kruglyak, B. N. Pshenichnyi, V. S. Kvakush, and Yu. I. Gorlov, ZhSKh, 6, 904, 1965.Google Scholar
  24. 24.
    Yu. A. Kruglyak, V. S. Kvakush, G. G. Dyadyusha, and V. I. Khil'chenko, Computational Methods in Quantum Chemistry [in Russian], issue 1, Naukova Dumka, Kiev, 1967.Google Scholar
  25. 25.
    I. V. Aleksandrov and N. D. Sokolov, DAN SSSR, 124, 115, 1959.Google Scholar
  26. 26.
    V. F. Bystrov, Dissertation, Moscow, 1963.Google Scholar
  27. 27.
    A. L. Buchachenko, DAN SSSR, 158, 932, 1964; A. L. Buchachenko and O. P. Sukhanova, ZhSKh, 6, 32, 1965.Google Scholar
  28. 28.
    V. F. Bystrov and V. P. Lezina, Opt. i spekt., 17, 538, 1964; L. A. Cohen, W. M. Jones, J. Am. Chem. Soc., 65, 3402, 1963; V. F. Bystrov, Yu. A. Zhdanova, and V. I. Minkina, Correlation Analysis in Organic Chemistry [in Russian], Izd. Rostov. Univ., 1966, section VII, ch. I, p. 416.Google Scholar

Copyright information

© The Faraday Press, Inc 1971

Authors and Affiliations

  • V. D. Pokhodenko
    • 1
  • V. S. Kuts
    • 1
  1. 1.Pisarzhevskii Institute of Physical ChemistryAS UkrSSRKiev

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