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Charge control in the formation of complexes of phenol with unsaturated compounds containing organometallic substituents from group IV

6. The effect of intermolecular interactions on the resonance effects in acetylene derivatives

  • Physical Chemistry
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

The resonance donor effect of the σ,π conjugation of R3M and R3MCH2 (M = Si, Ge, Sn; R is an alklyl group) substituents with the triple bond in compounds R3MC=CX and R3MCH2C≡CX (X = H, R) changes on passing from isolated molecules to their H-complexes. A partial δ+ charge on the triple bond enhances σ,π conjugation; a partial δ− charge on the triple bond has practically no effect on the resonance properties of R3M substituents, whereas the σ,π conjugation of R3MCH2 substituents diminishes owing to the effect of negative direct resonance interaction. The effect of σ,π conjugation on the effective negative charges of the carbon atoms in the -C≡C- fragments was estimated quantitatively.

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References

  1. A. N. Egorochkin, S. E. Skobeleva, V. L. Tsvetkova, and E. T. Bogoradovskii,Izv. Akad. Nauk, Ser. Khim., 1993, 2069 [Russ. Chem. Bull., 1993,42, 1982 (Engl. Transl.)].

  2. A. N. Egorochkin,Usp. Khim., 1992,61, 1092 [Russ. Chem. Rev., 1992,61 (Engl. Transl.)].

    Google Scholar 

  3. A. N. Egorochkin, G. A. Razuvaev, and M. A. Lopatin,J. Organometal. Chem., 1988,344, 49.

    Google Scholar 

  4. J. B. Lambert and R. A. Singer,J. Am. Chem. Soc., 1992,114, 10246.

    Google Scholar 

  5. A. N. Egorochkin, and G. A. Razuvaev,Usp. Khim., 1987,56, 1480 [Russ. Chem. Rev., 1987,56 (Engl. Transl.)].

    Google Scholar 

  6. P. G. Sennikov and A. N. Egorochkin,Usp. Khim., 1982,51, 561 [Russ. Chem. Rev., 1982,51 (Engl. Transl.)].

    Google Scholar 

  7. A. N. Egorochkin, S. E. Skobeleva, V. L. Tsvetkova, E. T. Bogoradovskii, and V. S. Zavgorodnii,Metalloorg. Khim., 1991,4, 362 [Organomet. Chem. USSR, 1991,4 (Engl. Transl.)].

    Google Scholar 

  8. S. Marriott and R. D. Topsom,J. Mol. Struct., 1984,106, 277.

    Google Scholar 

  9. Chemistry of Acetylenes, Ed. H. G. Viehe, Marcel Dekker, New York, 1969.

    Google Scholar 

  10. V. Jager, M. Murray, U. Niedballa, and H. G. Viehe,Methoden der Organischen Chemie (Houben-Weil), Ed. E. Muller, Georg Thieme Verlag, Stuttgart, 1977, 5/2a.

    Google Scholar 

  11. C. Hansch, A. Leo, and R. W. Taft,Chem. Rev., 1991,91, 165.

    Google Scholar 

  12. A. N. Egorochkin, S. E. Skobeleva, V. L. Tsvetkova, E. T. Bogoradovskii, V. N. Cherkasov, and V. S. Zavgorodnii,Metalloorg. Khim., 1991,4, 1095 [Organomet. Chem. USSR, 1991,4 (Engl. Transl.)].

    Google Scholar 

  13. M. G. Voronkov, N. I. Shergina, V. B. Pukhnarevich, L. V. Sherstyannikova, L. I. Kopylova, and B. A. Trofimov,Dokl. Akad. Nauk SSSR, 1975,224, 124 [Dokl. Chem., 1975,224 (Engl. Transl.)].

    Google Scholar 

  14. M. D. Joesten and L. J. Schaad,Hydrogen Bonding, M. Dekker, New York, 1974.

    Google Scholar 

  15. 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 

  16. A. N. Egorochkin, S. E. Skobeleva, and V. L. Tsvetkova,Metalloorg. Khim., 1993,6, 131 [Organomet. Chem. USSR, 1993,6 (Engl. Transl.)].

    Google Scholar 

  17. A. N. Egorochkin, S. E. Skobeleva, and V. L. Tsvetkova,Izv. Akad. Nauk, Ser. Khim., 1993, 1383 [Russ. Chem. Bull, 1993,42, 1316 (Engl. Transl.)].

    Google Scholar 

  18. M. H. Abraham, P. L. Grellier, D. V. Prior, P. P. Duce, J. J. Morris, and P. J. Taylor,J. Chem. Soc. Perkin Trans. 2, 1989, 699.

    Google Scholar 

  19. C. Laurence and R. Queignec,J. Chem. Soc. Perkin Trans. 2, 1992, 1915.

    Google Scholar 

  20. O. V. Sverdlova, S. E. Gnitsevich, Z. A. Shevchenko, and I. A. Favorskaya,Zh. Org. Khim., 1975,11, 1173 [J. Org. Chem. USSR, 1975,11 (Engl. Transl.)].

    Google Scholar 

  21. P. Hobza and R. Zahradnik,Chem. Rev., 1988,88, 871.

    Google Scholar 

  22. A. N. Egorochkin, S. E. Skobeleva, V. L. Tsvetkova, E. T. Bogoradovskii, and V. S. Zavgorodnii,Metalloorg. Khim., 1990,3, 322 [Organomet. Chem. USSR, 1990,3 (Engl. Transl.)].

    Google Scholar 

  23. A. Pross, L. Radom, and R. W. Taft,J. Organic Chem., 1980,45, 818.

    Google Scholar 

  24. A. N. Egorochkin, S. E. Skobeleva, V. L. Tsvetkova, E. T. Bogoradovskii, and V. S. Zavgorodnii,Metalloorg. Khim., 1992,5, 1342 [Organomet. Chem. USSR, 1992,5 (Engl. Transl.)].

    Google Scholar 

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Authors and Affiliations

  1. Institute of Organometallic Chemistry, Russian Academy of Sciences, 49 ul. Tropinina, 603600, Nizhnii Novgorod, Russian Federation

    A. N. Egorochkin & S. E. Skobeleva

  2. Technological Institute, 198013, St. Petersburg, Russain Federation

    E. T. Bogoradovsky & T. P. Zubova

Authors
  1. A. N. Egorochkin
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  2. S. E. Skobeleva
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  3. E. T. Bogoradovsky
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  4. T. P. Zubova
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Additional information

Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1041–1046, June, 1994.

This work was supported by the Russian Fundation for Basic Research (Grant 93-03-18372).

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Egorochkin, A.N., Skobeleva, S.E., Bogoradovsky, E.T. et al. Charge control in the formation of complexes of phenol with unsaturated compounds containing organometallic substituents from group IV. Russ Chem Bull 43, 976–982 (1994). https://doi.org/10.1007/BF01558061

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  • DOI: https://doi.org/10.1007/BF01558061

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