Skip to main content
Log in

New approach to stereochemical structure determination of bis-selenium-subsituted alkenes

  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

A new approach to determination of the stereochemical structure of bis-selenium-substituted alkenes using experimental 77Se NMR studies and B3LYP/6-311G(d) quantum-chemical calculations is developed. Joint analysis of experimental and calculated data allows assignment of signals in the 77Se NMR spectrum. The method was evaluated taking the model compounds (PhSe)HC=C(SePh)R (R = COOMe, CH2NMe2, CH2OH, Ph) as examples.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Catalytic Heterofunctionalization, Eds. A. Togni and H. Grützmacher, Wiley-VCH, Weinheim, 2001.

  2. I. P. Beletskaya and C. Moberg, Chem. Rev., 1999, 99, 3435.

    Google Scholar 

  3. O. N. Temkin, G. K. Shestakov, and Yu. A. Treger, Atsetilen: Khimiya. Mekhanizmy reaktsii. Tekhnologiya [Acetylene: Chemistry. Reaction Mechanisms. Technology], Ed. O. N. Temkin, Khimiya, Moscow, 1991, 416 pp. (in Russian).

    Google Scholar 

  4. A. Yamamoto, Organotransition Metal Chemistry, Wiley, New York, 1986.

    Google Scholar 

  5. Accurate Molecular Structure: Their Determination and Importance, Eds. A. Domenicano and I. Hargittai, Oxford University Press, Oxford, 1992.

  6. D. Neuhaus and M. P. Williamson, The Nuclear Overhauser Effect in Structural and Conformational Analysis, VCH, New York, 1989.

    Google Scholar 

  7. M. P. Williamson, in Encyclopedia of Nuclear Magnetic Resonance, Eds. D. M. Grant and R. K. Harris, Wiley, Chichester, 1996, 5, p. 3262.

    Google Scholar 

  8. K. Wolinski, J. F. Hilton, and P. Pulay, J. Am. Chem. Soc., 1990, 112, 8251.

    Google Scholar 

  9. R. Ditchfield, Mol. Phys., 1974, 27, 789.

    Google Scholar 

  10. W. Koch and M. C. Holthausen, A Chemist's Guide to Density Functional Theory, Wiley-VCH, Weinheim, 2001, 300 pp.

    Google Scholar 

  11. T. Helgaker, M. Jaszunski, and K. Ruud, Chem. Rev., 1999, 99, 293.

    Google Scholar 

  12. J. R. Cheeseman, G. W. Trucks, T. A. Keith, and M. J. Frisch, J. Chem. Phys., 1996, 104, 5497.

    Google Scholar 

  13. G. Rauhut, S. Puyear, K. Wolinski, and P. Pulay, J. Phys. Chem., 1996, 100, 6310.

    Google Scholar 

  14. W. Nakanishi and S. Hayashi, J. Phys. Chem., A, 1999, 103, 6074.

    Google Scholar 

  15. V. P. Ananikov, I. P. Beletskaya, G. G. Aleksandrov, and I. L. Eremenko, Organometallics, 2003, 22, 1414.

    Google Scholar 

  16. H. Kuniyasu, A. Ogawa, S.-I. Miyazaki, I. Ryu, N. Kambe, and N. Sonoda, J. Am. Chem. Soc., 1991, 113, 9796.

    Google Scholar 

  17. G. Bodenhausen, H. Kogler, and R. R. Ernst J. Magn. Reson., 1984, 58, 370.

    Google Scholar 

  18. R. Wagner and S. Berger, J. Magn. Reson., Ser. A, 1996, 123, 119.

    Google Scholar 

  19. A. Bax and R. Freeman, J. Magn. Reson., 1981, 44, 542.

    Google Scholar 

  20. J. Ruiz-Cabello, G. W. Vuister, C. T. W. Moonen, P. van Gelderen, J. S. Cohen, and C. M. van Zijl, J. Magn. Reson., 1992, 100, 282.

    Google Scholar 

  21. W. Willker, D. Leibfritz, R. Kerssebaum, and W. Bermel, Magn. Reson. Chem., 1993, 31, 287.

    Google Scholar 

  22. A. D. Becke, Phys. Rev., A, 1988, 38, 3098.

    Google Scholar 

  23. C. Lee, W. Yang, and R. G. Parr, Phys. Rev., B, 1988, 37 , 785.

    Google Scholar 

  24. A. D. Becke, J. Chem. Phys., 1993, 98, 5648.

    Google Scholar 

  25. R. Ditchfield, W. J. Hehre, and J. A. Pople, J. Chem. Phys., 1971, 54, 724.

    Google Scholar 

  26. R. Krishnan, J. S. Binkley, R. Seeger, and J. A. Pople, J. Chem. Phys., 1980, 72, 650.

    Google Scholar 

  27. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery Jr, R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle, and J. A. Pople, GAUSSIAN-98, Rev. A.7, Gaussian, Pittsburgh (PA), 1998.

    Google Scholar 

  28. H. Duddeck, Prog. NMR Spectrosc., 1995, 27, 1.

    Google Scholar 

  29. H. Gunther, NMR Spectroscopy, John Wiley and Sons Ltd, Chichester, 1996, 581 pp.

    Google Scholar 

  30. M. H. Levitt, J. Magn. Reson., 1997, 126, 164.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Ananikov, V.P., Beletskaya, I.P. New approach to stereochemical structure determination of bis-selenium-subsituted alkenes. Russian Chemical Bulletin 52, 811–816 (2003). https://doi.org/10.1023/A:1024423603695

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1024423603695

Navigation