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Russian Chemical Bulletin

, Volume 44, Issue 2, pp 280–286 | Cite as

Charge control of the complex formation of phenol with unsaturated compounds containing organoelement substituents from group IV

8. Furan derivatives
  • A. N. Egorochkin
  • S. E. Skobeleva
  • T. G. Mushtina
Physical Chemistry

Abstract

The frequency shifts (Δv (OH)) of phenol and the resonance components (δvr) of these shifts in the IR spectra of forty H-complexes of phenol with furan derivatives containing organic, organosilicon, organogermanium, and organotin substituents are studied. The values of Δv and ΔvR are linearly related to quantum chemical parameters of the variation of the effective charges of the furan ring atoms affected by σ- and π-interactions with organic substituents. The effect of the conjugation between an organoelement substituent and the furan ring on the effective charges is estimated. The resonance parameters (σR) of organoelement substituents in derivatives of benzene, thiophene, and furan and the reasons for the non-versatility of σR are considered.

Key words

furan derivatives H-complexes charge control of complex formation effective charge non-versatility of resonance parameters 

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References

  1. 1.
    A. N. Egorochkin and S. E. Skobeleva,Izv. Akad. Nauk, Ser. Khim., 1994, 2163 [Russ. Chem. Bull., 1994,42 (Engl. Transl.)].Google Scholar
  2. 2.
    A. N. Egorochkin, S. E. Skobeleva, V. L. Tsvetkova, E. T. Bogoradovskii, and V. S. Zavgorodnii,Metalloorg. Khim., 1992,5, 818 [Organomet. Chem. USSR, 1992,5 (Engl. Transl.)].Google Scholar
  3. 3.
    A. N. Egorochkin, S. E. Skobeleva, and V. L. Tsvetkova,Metalloorg. Khim., 1993,6, 131 [Organomet. Chem. USSR, 1993,6 (Engl. Transl.)].Google Scholar
  4. 4.
    A. N. Egorochkin, S. E. Skobeleva, V. L. Tsvetkova,Izv. Akad. Nauk. Ser. Khim., 1993, 1383 [Russ. Chem. Bull., 1993,42, 1316 (Engl. Transl.)].Google Scholar
  5. 5.
    A. C. Legon and D. J. Miller,Chem. Soc. Rev., 1987,16, 467.Google Scholar
  6. 6.
    S. Scheiner, inReviews in Computational Chemistry, Eds. K. B. Lipkowitz and D. B. Boyd, VCH Publishers, New York, 1991,2, 165.Google Scholar
  7. 7.
    C. Hansch, A. Leo, and R. W. Taft,Chem. Rev., 1991,91, 165.Google Scholar
  8. 8.
    A. N. Egororchkin and G. A. Razuvaev,Usp. Khim., 1987,56, 1480 [Russ. Chem. Rev., 1987,56 (Engl. Transl.)].Google Scholar
  9. 9.
    Z. Yoshida and E. Osawa,J. Am. Chem. Soc., 1966,88, 4019.Google Scholar
  10. 10.
    A. N. Egorochkin, S. E. Skobeleva, M. A. Lopatin, A. A. Tumanov, E. Ya. Lukevits, N. P. Erchak, and V. F. Matorykina,Dokl. Akad. Nauk, 1984,275, 909 [Dokl. Chem., 1984,275 (Engl. Transl.)].Google Scholar
  11. 11.
    M. D. Joesten and L. J. Schaad,Hydrogen Bonding, Ed. M. Dekker New York, 1974.Google Scholar
  12. 12.
    M. A. Abraham, P. L. Grellier, D. V. Prior, J. J. Morris, and P. J. Taylor,J. Chem. Soc. Perkin Trans. 2, 1990, 521.Google Scholar
  13. 13.
    N. T. Nguyen, A. F. Hegarty, T.-K. Ha, and G. R. De Mare,J. Chem. Soc. Perkin Trans. 2, 1986, 147.Google Scholar
  14. 14.
    R. Houriet, E. Rolli, G. Bouchoux, and Y. Hoppilliard,Helv. Chim. Acta, 1985,68, 2037.Google Scholar
  15. 15.
    G. Klopman, inChemical Reactivity and Reaction Paths, Ed. G. Klopman, Wiley, New York, 1974,4.Google Scholar
  16. 16.
    P. G. Pearson,J. Molec. Struct. (Theochem), 1992,255, 261.Google Scholar
  17. 17.
    I. G. John and L. Radom,J. Am. Chem. Soc., 1978,100, 3981.Google Scholar
  18. 18.
    Y. Apeloig, inThe Chemistry of Organic Silicon Compounds, Eds. S. Patai, Z. Rappoport, Wiley, Chichester, 1989,1, 57.Google Scholar
  19. 19.
    A. N. Egorochkin,Usp. Khim., 1992,61, 1092 [Russ. Chem. Rev., 1992,61 (Engl. Transl.)].Google Scholar
  20. 20.
    M. C. Moreau-Descoings, G. Goethals, J. P. Sequin, and J. P. Doncet,J. Molec. Struct., 1988,177, 407.Google Scholar
  21. 21.
    A. N. Egorochkin, S. E. Skobeleva, E. T. Bogoradovskii, and T. P. Zubova,Izv. Akad. Nauk, Ser. Khim., 1994, 1047 [Russ. Chem. Bull., 1994,43, 976 (Engl. Transl.)].Google Scholar
  22. 22.
    V. N. Baidin, I. I. Kritskaya, M. M. Timoshenko, Yu. A. Ustynyuk, and Yu. V. Chizhov, inUspekhi fotoniki [Advance in Photonics], Leningrad State University, Leningrad, 1983, 8 (in Russian).Google Scholar
  23. 23.
    V. I. Nefedov and V. I. Vovna,Elektronnaya struktura organicheskikh i elementoorganicheskikh soedinenii [Electronic Structure of Organic and Organometallic Compounds], Nauka, Moscow, 1989, 62 (in Russian).Google Scholar
  24. 24.
    A. N. Egorochkin, M. A. Lopatin, and G. A. Razuvaev,Dokl. Akad Nauk SSSR, 1988,299, 909 [Dokl. Chem., 1988,299 (Engl. Transl.)].Google Scholar
  25. 25.
    M. A. Lopatin, V. A. Kuznetsov, A. N. Egorochkin, O. A. Pudova, N. P. Erchak, and E. Ya. Lukevits,Dokl. Akad. Nauk SSSR, 1979,246, 379 [Dokl. Chem., 1979,246 (Engl. Transl.)].Google Scholar

Copyright information

© Plenum Publishing Corporation 1995

Authors and Affiliations

  • A. N. Egorochkin
    • 1
  • S. E. Skobeleva
    • 1
  • T. G. Mushtina
    • 1
  1. 1.Institute of Organometallic ChemistryRussian Academy of SciencesNizhnii NovgorodRussian Federation

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