Skip to main content
SpringerLink
Log in

Study of conjugation effects by means of NMR spectroscopy 21. Factor analysis of NMR parameters of alkyl phenyl ethers and sulfides

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

Conclusions

Increases of effective volume of the alkyl group in the series of alkyl phenyl ethers does not lead to any decrease of π-donor properties of the oxygen atom except in the case of the last member of the series investigated, tert-butoxybenzene; in contrast, in the series of alkyl phenyl sulfides, sharp inhibition of conjugation is observed even in isopropylthiobenzene, and in tert-butylthiobenzene, the sulfur atom manifests weak π-acceptor properties.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Literature cited

  1. V. M. Bzhezovskii, G. A. Kalabin, I. A. Aliev, B. A. Trofimov, M. A. Shakhgel'diev, and A. M. Kuliev, Izv. Akad. Nauk SSSR, Ser. Khim., 1999 (1976).

  2. G. A. Kalabin, L. B. Krivdin, and B. A. Trofimov, Izv. Akad. Nauk SSSR, Ser. Khim., 113 (1982).

  3. L. B. Krivdin, G. A. Kalabin, and B. A. Trofimov, Izv. Akad. Nauk SSSR, Ser. Khim., 275 (1982).

  4. L. B. Krivdin, G. A. Kalabin, and B. A. Trofimov, Izv. Akad. Nauk SSSR, Ser. Khim., 565 (1982).

  5. L. B. Krivdin, G. A. Kalabin, and B. A. Trofimov, Izv. Akad. Nauk SSSR, Ser. Khim., 570 (1982).

  6. J. M. Read, Jr., R. E. Mayo, and J. H. Goldstein, J. Mol. Spectrosc.,22, 419 (1967).

    Google Scholar 

  7. F. J. Weigert and J. D. Roberts, J. Am. Chem. Soc.,89, 2967 (1967).

    PubMed  Google Scholar 

  8. A. R. Tarpley, Jr., and J. H. Goldstein, J. Phys. Chem.,76, 515 (1972).

    Google Scholar 

  9. J. P. Jacobsen and K. Schaumburg, Mol. Phys.,28, 1505 (1974).

    Google Scholar 

  10. M. Hansen and H. F. Jacobsen, J. Magn. Reson.,20, 520 (1975).

    Google Scholar 

  11. V. A. Chertkov and N. M. Sergeev (Sergeyev), J. Magn. Reson.,21, 159 (1976).

    Google Scholar 

  12. L. Ernst, V. Wray, V. A. Chertkov, and N. M. Sergeev (Sergeyev), J. Magn. Reson.,25, 123 (1977).

    Google Scholar 

  13. P. S. Dewar, E. Ernstbrunner, J. R. Gilmore, M. Godfrey, and J. M. Mellor, Tetrahedron,30, 2455 (1974).

    Google Scholar 

  14. A. R. Katritzky, R. F. Pinzelli, and R. D. Topsom, Tetrahedron,28, 3441 (1972).

    Google Scholar 

  15. G. A. Kalabin and D. F. Kushnarev, Dokl. Akad. Nauk SSSR,254, 1425 (1980).

    Google Scholar 

  16. G. A. Kalabin, D. F. Kushnarev, R. B. Valeev, B. A. Trofimov, and M. A. Fedotov, Org. Magn. Reson.,18, 1 (1982).

    Google Scholar 

  17. D. N. Lawley and A. E. Maxwell, Factor Analysis as a Statistical Method, 2nd edn., American Elsevier, New York (date of publication not given; Russian translation published 1976).

    Google Scholar 

  18. M. Mishima, M. Fujio, R. Takeda, and Y. Tsuno, Mem. Fac. Sci. Kyusuu Univ., Ser. C,11, 97 (1978).

    Google Scholar 

  19. D. F. Ewing, Org. Magn. Reson.,12, 499 (1979).

    Google Scholar 

  20. M. P. Williamson, R. J. Kostelnik, and S. M. Castellano, J. Chem. Phys.,49, 2218 (1968).

    Google Scholar 

  21. V. Wray, L. Ernst, and E. Lustig, J. Magn. Reson.,27, 1 (1977).

    Google Scholar 

  22. N. M. Sergeev, Dissertation, Moscow (1981).

  23. V. M. Bzhezovskii, G. N. Dolenko, G. A. Kalabin, V. A. Topchii, V. A. Aliev, G. K. Parygina, and B. A. Trofimov, Izv. Akad. Nauk SSSR, Ser. Khim., 1784 (1981).

  24. A. A. Bothner-By and S. Castellano, in: Computer Programs for Chemistry, D. F. Tar, ed., W. A. Benjamin, New York (1968), Vol. 1, p. 10.

  25. W. E. Hull, Bruker Report, 23 (1979).

Download references

Author information

Authors and Affiliations

  1. Irkutsk Institute of Organic Chemistry, Siberian Branch of the Academy of Sciences of the USSR, USSR

    L. B. Krivdin, V. I. Donskikh, G. A. Kalabin & B. A. Trofimov

  2. A. A. Zhdanov Irkutsk State University, USSR

    L. B. Krivdin, V. I. Donskikh, G. A. Kalabin & B. A. Trofimov

Authors
  1. L. B. Krivdin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. I. Donskikh
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. G. A. Kalabin
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. B. A. Trofimov
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 1053–1059, May, 1983.

The authors wish to thank V. A. Chertkov for assistance in performing the experiment and discussion of the results that were obtained.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Krivdin, L.B., Donskikh, V.I., Kalabin, G.A. et al. Study of conjugation effects by means of NMR spectroscopy 21. Factor analysis of NMR parameters of alkyl phenyl ethers and sulfides. Russ Chem Bull 32, 953–958 (1983). https://doi.org/10.1007/BF00956145

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00956145

Keywords

Search

Navigation