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Synthesis and19F-{1H} NMR spectra of 4-fluorophenylacetylene and its organometallic derivatives

  • Organic Chemistry
  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    A19F NMR spectroscopic study of 4-fluorophenylacetylene and its derivatives showed that the electron-withdrawing capacity of the C≡CX groups increases in the following series for X: cyclo-C6H11Hg < MeHg < PhHg ≈ Ph3C ≈ Ph3Pb < Ph3Sn < H < Ph3Ge.

  2. 2.

    The formation of a hydrogen bond or coordination bond of coordinating solvents with these compounds makes a significant contribution to the change in the electronic effect of the C≡CX groups and this contribution increases in the following series for X: Ph3Sn < Ph3-Pb < H ≈ cyclo-C6H11Hg < MeHg < PhHg.

  3. 3.

    4-Fluorophenylacetylene and its organometallic derivatives are convenient model compounds for the study of metal-proton and metal-metal exchange reactions.

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Literature cited

  1. L. A. Fedorov, A. S. Peregudov, and D. N. Kravtsov, Usp. Khim.,48, 1572 (1979).

    Google Scholar 

  2. A. S. Peregudov, V. F. Ivanov, D. N. Kravtsov, and L. A. Fedorov, Izv. Akad. Nauk SSSR, Ser. Khim., 1674 (1981).

  3. D. N. Kravtsov, A. S. Peregudov, and V. F. Ivanov, Izv. Akad. Nauk SSSR, Ser. Khim., 522 (1983).

  4. A. D. Allen and C. D. Cook, Can. J. Chem.,41, 1084 (1963).

    Google Scholar 

  5. H. G. Viene, The Chemistry of Acetylenes, Marcel Dekker, New York (1969).

    Google Scholar 

  6. M. C. Esquivel, A. S. Macias, and L. B. Reventos, Inorg. and Nucl. Chem.,39, 1153 (1977).

    Google Scholar 

  7. J. W. Emsley and L. Phillips, Mol. Phys.,11, 437 (1966).

    Google Scholar 

  8. R. D. Green, Hydrogen Bonding by C-H Groups, MacMillan Press, London (1974).

    Google Scholar 

  9. R. W. Taft, E. Price, I. R. Fox, I. C. Lewis, K. K. Andersen, and G. T. Davis, J. Am. Chem. Soc.,85, 3146 (1963).

    Google Scholar 

  10. O. A. Osipov, V. I. Minkin, and A. D. Garnovskii, Dipole Moment Handbook [in Russian], Izd. Vysshaya Shkola, Moscow (1971).

    Google Scholar 

  11. K. C. Ingold, Reaction Mechanisms and the Structure of Organic Compounds [Russian translation], Inostr. Lit., Moscow (1959), p. 112.

    Google Scholar 

  12. T. R. Griffiths and D. C. Pugh, Coord. Chem. Rev.,29, 129 (1979).

    Google Scholar 

  13. L. J. Andrews and R. M. Keefer, Molecular Complexes in Organic Chemistry, Holden-Day (1964).

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Author information

Authors and Affiliations

  1. A. N. Nesmeyanov Institute of Heteroorganic Compounds, Academy of Sciences of the USSR, Moscow

    A. S. Peregudov, V. F. Ivanov, D. N. Kravtsov & É. I. Fedin

Authors
  1. A. S. Peregudov
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  2. V. F. Ivanov
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  3. D. N. Kravtsov
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  4. É. I. Fedin
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 849–855, April, 1984.

The authors express their gratitude to L. S. Golovchenko for providing a sample of 4,4′-difluorodiphenyltolan.

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Peregudov, A.S., Ivanov, V.F., Kravtsov, D.N. et al. Synthesis and19F-{1H} NMR spectra of 4-fluorophenylacetylene and its organometallic derivatives. Russ Chem Bull 33, 783–787 (1984). https://doi.org/10.1007/BF00947833

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  • DOI: https://doi.org/10.1007/BF00947833

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