Advertisement

Chemistry of Heterocyclic Compounds

, Volume 26, Issue 5, pp 495–502 | Cite as

Heteroorganic derivatives of furan. 65. Effect of substituents on shielding of 1H, 13C, and 29Si and 29Si-13C spin-spin coupling constants in NMR spectra of 2-substituted furans and 5-trimethylsilylfurans

  • Yu. Yu. Popelis
  • É. É. Liepin'sh
  • Z. P. Bruveris
  • É. Lukevits
Article

Abstract

The results of an investigation of 2-substituted furans and 5-trimethylsilylfurans by NMR spectroscopy and the CNDO/2 method showed that the chemical shifts of the different nuclei do not correlate sufficiently clearly with the calculated charges because of an additional change in the electron density under the influence of a π-d interaction. The 13C-29Si direct spin-spin coupling constants (SSCC) are less sensitive to this interaction, since they depend primarily on the inductive effects of the substituents.

Keywords

Spectroscopy Organic Chemistry Chemical Shift Furan Inductive Effect 
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.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature Cited

  1. 1.
    S. V. Skobeleva, A. N. Egorochkin, V. L. Tsvetkova, N. E. Tyulina, N. P. Erchak, and É. Lukevits, Izv. Akad. Nauk Latv. SSR, Ser. Khim., No. 3, 355 (1988).Google Scholar
  2. 2.
    A. N. Egorochkin, é. Lukevits, and M. G. Voronkov, Khim. Geterotsikl. Soedin., No. 4, 499 (1965).Google Scholar
  3. 3.
    é. Lukevits, N. P. Erchak, Yu. Yu. Popelis, and R. M. Zolotoyabko, The Chemistry of Heteroorganic Compounds [in Russian], Nauka, Leningrad (1976), p. 63.Google Scholar
  4. 4.
    D. Doddrell, K. G. Lewis, C. E. Mulquiney, W. Adcock, W. Kitching, and M. Bullpitt, Aust. J. Chem. 27, 417 (1974).Google Scholar
  5. 5.
    M. MÄgi, E. Lippmaa, E. Lukevics, and N. P. Jercak, Org. Magn. Reson. 9, 299 (1977).Google Scholar
  6. 6.
    K. B. Wiberg, Tetrahedron 24, 1083 (1968).Google Scholar
  7. 7.
    S. Gronowitz, I. Johnson, and A.-B. Hörnfeldt, Chem. Scripta 7, 211 (1975).Google Scholar
  8. 8.
    S. Fliszar, Charge Distribution and Chemical Effects, Springer, New York-Berlin-Tokyo (1983), p. 47.Google Scholar
  9. 9.
    H. Günther, Introduction to a Course in NMR Spectroscopy [Russian translation], Mir, Moscow (1984), pp. 31, 79.Google Scholar
  10. 10.
    C. R. Ernst, L. Spialter, G. R. Buell, and D. L. Wilhite, J. Am. Chem. Soc. 96, 5375 (1974).Google Scholar
  11. 11.
    Yu. Yu. Popelis, é. é. Liepin'sh, and Ya. P. Stradyn', Khim. Geterotsikl. Soedin., No. 2, 167 (1980).Google Scholar
  12. 12.
    A. N. Egorochkin, N. S. Vyazankin, and S. Ya. Khorshev, Usp. Khim. 51, 828 (1972).Google Scholar
  13. 13.
    G. Fritz and P. Boettinger, Z. Anorg. Chem. 385, 159 (1973).Google Scholar
  14. 14.
    R. Loewer, M. Vongehr, and H. C. Marsmann, Chem. Zeitung 99, 33 (1975).Google Scholar
  15. 15.
    N. P. Erchak, R. N. Ziatdinova, O. A. Litvinov, V. A. Naumov, and é. Lukevits, Khim. Geterotsikl. Soedin., No. 1, 25 (1987).Google Scholar
  16. 16.
    L. A. Fedorov, NMR Spectroscopy of Organometallic Compounds [in Russian], Nauka, Moscow (1984).Google Scholar
  17. 17.
    H. A. Bent, Chem. Rev. 61, 275 (1961).Google Scholar
  18. 18.
    L. A. Fedorov, é. I. Fedin, B. A. Kvasov, and I. A. Beletskaya, Zh. Strukt. Khim. 10, 247 (1969).Google Scholar
  19. 19.
    D. M. Dodrell, D. T. Pegg, W. Brooks, and M. R. Bendall, J. Am. Chem. Soc. 103, 727 (1981).Google Scholar
  20. 20.
    J. Schraml, Coll. Czech. Chem. Commun. 48, 3402 (1983).Google Scholar
  21. 21.
    N. B. Chapman and J. Shorter (eds.), Correlation Analysis in Chemistry, Plenum Press, New York-London (1978), p. 455.Google Scholar
  22. 22.
    Ya. Ya. Bleidelis, Advances in the Chemistry of Furan [in Russian], Zinatne, Riga (1978), Chap. 1.Google Scholar
  23. 23.
    H. N. Nimeyer, Tetrahedron 33, 1369 (1977).Google Scholar

Copyright information

© Plenum Publishing Corporation 1990

Authors and Affiliations

  • Yu. Yu. Popelis
    • 1
  • É. É. Liepin'sh
    • 1
  • Z. P. Bruveris
    • 1
  • É. Lukevits
    • 1
  1. 1.Institute of Organic SynthesisLatvian Academy of SciencesRiga

Personalised recommendations