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Effect of intramolecular hydrogen bond in nucleophilic azaheteroaromatic substitution reaction

  • O. P. Petrenko
  • V. P. Krivopalov
  • V. V. Lapachev
  • V. P. Mamaev
Organic Chemistry

Conclusions

  1. 1.

    An experimental and theoretical study was made of the accelerating effect of the intramolecular hydrogen bond on the nucleophilic substitution reaction of halopyrimidines.

     
  2. 2.

    In contrast to the existing literature data, the presence of specific solvation is not a necessary condition for the accelerating effect.

     
  3. 3.

    The theory was expressed that intrachelate tautomerism is possible in the σ complexes of azines that contain an intramolecular hydrogen bond.

     

Keywords

Hydrogen Hydrogen Bond Intramolecular Hydrogen Bond Nucleophilic Substitution Substitution Reaction 
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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Literature cited

  1. 1.
    R. Pater, J. Heterocycl. Chem.,7, 1113 (1970).Google Scholar
  2. 2.
    I. D. Sadekov, V. I. Minkin, and A. E. Lutskii, Usp. Khim.,39, 380 (1970).Google Scholar
  3. 3.
    S. Tsunoda, Y. Hashida, S. Sekiguchi, and K. Matsui, Bull. Chem. Soc. Jpn.,49, 487 (1976).Google Scholar
  4. 4.
    O. A. Zagulyaeva, S. M. Shein, A. I. Shvets, V. P. Mamaev, and V. P. Krivopalov, Reakts. Sposobn. Org. Soedin.,7, 1133 (1970).Google Scholar
  5. 5.
    V. P. Mamaev, O. A. Zagulyaeva, S. M. Shein, A. I. Shvets, and V. P. Krivopalov, Reakts. Sposobn. Org. Soedin.,5, 824 (1968).Google Scholar
  6. 6.
    J. A. Pople and D. L. Beveridge, Approximate Molecular Orbital Theory, McGraw-Hill, New York (1970).Google Scholar
  7. 7.
    R. Pearson, Symmetry Rules for Chemical Reactions, Wiley-Interscience, New York (1976).Google Scholar
  8. 8.
    O. S. Tee and K. Yates, J. Am. Chem. Soc.,94, 3074 (1972).Google Scholar
  9. 9.
    P. J. Wheatley, Acta Crystallogr.,13, 80 (1960).Google Scholar
  10. 10.
    H. M. Niemeyer, Tetrahedron,33, 1369 (1977).Google Scholar
  11. 11.
    T. Kato, H. Yamanaka, and T. Sibata, J. Pharm. Soc. Japan,87, 1096 (1967); Ref. Zh., Khim., 14J350 (1968).Google Scholar
  12. 12.
    H. J. Minnemeyer, P. B. Clarke, and H. Tieckelmann, J. Org. Chem.,31, 406 (1966).Google Scholar
  13. 13.
    B. Lithgoe and L. Rayner, J. Chem. Soc.,1951, 2323.Google Scholar
  14. 14.
    V. P. Krivopalov and V. P. Mamaev, Khim. Geterotsikl. Soedin.,1979, 987.Google Scholar

Copyright information

© Plenum Publishing Corporation 1981

Authors and Affiliations

  • O. P. Petrenko
    • 1
  • V. P. Krivopalov
    • 1
  • V. V. Lapachev
    • 1
  • V. P. Mamaev
    • 1
  1. 1.Novosibirsk Institute of Organic ChemistrySiberian Branch of the Academy of SciencesUSSR

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