Skip to main content
SpringerLink
Log in

Synthesis and 13C NMR features of N-substituted aziridino[60]fullerenes

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

An effective cycloaddition of organic azides to fullerene C60 in the presence stoichiometric amounts of Cu(OTf)2 to form individual aziridino[60]fullerenes was developed. Considering the 13C NMR data, it was ascertained that among the synthesized aziridinofullerenes only the compound with the adamantane substituent possessed the local C2v symmetry of the fullerene core. In the 13C NMR spectra of the other compounds, 11 resonances were unexpectedly observed for the fullerene carbon atoms instead of probable 16 signals. The 13C NMR chemical shifts were computed with the high level GIAO-PBE/3ζ technique and the possible reasons of the signal overlap in the 13C NMR spectra were discussed.

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

References

  1. M. R. Banks, J. I. G. Cadogan, I. Gosney, P. K. G. Hodgson, P. R. R. Langridge-Smith, J. R. A. Millar, J. A. Parkinson, D. W. H. Rankina, A. T. Taylor, J. Chem. Soc., Chem. Commun., 1995, 887.

    Google Scholar 

  2. F. Diederich, C. Thilgen, Science, 1996, 271, 317.

    Article  CAS  Google Scholar 

  3. M. Prato, V. Lucchini, M. Maggini, E. Stimpfl, G. Scorrano, M. Eiermann, T. Suzuki, F. Wudl, J. Am. Chem. Soc., 1993, 115, 8479.

    Article  CAS  Google Scholar 

  4. F. Diederich, L. Isaccs, D. J. Philp, Chem. Soc., Perkin Trans. 2, 1994, 391.

    Google Scholar 

  5. K. M. Creegan, J. L. Robbins, W. K. Robbins, J. M. Millar, R. D. Sherwood, P. J. Tindall, D. M. Cox, A. B. Smith III, J. P. McCauley, Jr., D. R. Jones, R. T. Gallagher, J. Am. Chem. Soc., 1992, 114, 1103.

    Article  CAS  Google Scholar 

  6. Y. Elemes, S. K. Silverman, C. Sheu, M. Kao, C. S. Foote, M. M. Alvarez, R. L. Whetton, Angew. Chem., Int. Ed., 1992, 31, 351.

    Article  Google Scholar 

  7. A. B. Smith III, R. M. Strongin, L. Brard, G. T. Furst, W. J. Romanow, K. G. Owens, R. C. King, J. Am. Chem. Soc., 1993, 115, 5829.

    Article  Google Scholar 

  8. A. B. Smith III, R. M. Strongin, L. Brard, G. T. Furst, W. J. Romanow, K. G. Owens, R. J. Goldschmidt, R. C. King, J. Am. Chem. Soc., 1995, 117, 5492.

    Article  Google Scholar 

  9. M. R. Banks, J. I. G. Cadogan, I. Gosney, P. K. G. Hodgson, P. R. R. Langridge-Smith, J. R. A. Millar, A. T. Taylor, J. Chem. Soc., Chem. Commun., 1995, 885.

    Google Scholar 

  10. J. Averdung, H. Luftmann, J. Mattay, K.-U. Claus, W. Abraham, Tetrahedron Lett., 1995, 36, 2957.

    Article  CAS  Google Scholar 

  11. A. R. Akhmetov, A. R. Tuktarov, U. M. Dzhemilev, I. R. Yarullin, L. A. Gabidullina, Russ. Chem. Bull. (Int. Ed.), 2011, 60, 1885 [Izv. Akad. Nauk, Ser. Khim., 2011, 1852].

    Article  CAS  Google Scholar 

  12. E. L. Eliel, S. H. Wilen, M. P. Doyle, Basic Organic Stereochemistry, Wiley-Intersci., Hoboken, 2001, 704 pp.

    Google Scholar 

  13. M. Yan, S. X. Cai, J. F. W. Keana, J. Org. Chem., 1994, 59, 5951.

    Article  CAS  Google Scholar 

  14. T. Nakahodo, M. Okada, H. Morita, T. Yoshimura, M. O. Ishitsuka, T. Tsuchiya, Y. Maeda, H. Fujihara, T. Akasaka, X. Gao, S. Nagase, Angew. Chem., Int. Ed., 2008, 47, 1298.

    Article  CAS  Google Scholar 

  15. I. P. Romanova, G. G. Yusupova, O. A. Larionova, A. A. Balandina, Sh. K. Latypov, V. V. Zverev, D. G. Yakhvarov, G. L. Rusinov, O. G. Sinyashin, Russ. Chem. Bull. (Int. Ed.), 2006, 55, 502 [Izv. Akad. Nauk, Ser. Khim., 2006, 484].

    Article  CAS  Google Scholar 

  16. A. R. Tuktarov, A. R. Akhmetov, U. M. Dzhemilev, in Fullerenes: Chemistry, Natural Sources and Technological Applications, Ed. S. B. Ellis, Nova Sci. Publ., New York, 2014, p.123.

  17. H. Hachiya, T. Kakuta, M. Takami, Y. Kabe, J. Organomet. Chem., 2009, 694, 630.

    Article  CAS  Google Scholar 

  18. M. Okada, T. Nakahodo, M. O. Ishitsuka, H. Nikawa, T. Tsuchiya, T. Akasaka, T. Fujie, T. Yoshimura, Z. Slanina, S. Nagase, Chem. - Asian J., 2011, 6, 416.

    Article  CAS  Google Scholar 

  19. N. Ikuma, T. Mikie, Y. Doi, K. Nakagawa, K. Kokubo, T. Oshima, Org. Lett., 2012, 14, 6040.

    Article  CAS  Google Scholar 

  20. L. Shuzhi, T. Guangshi, Prog. Chem., 2004, 16, 561 (in Chinese).

    Google Scholar 

  21. M. S. Meier, H. P. Spielmann, R. G. Bergosh, R. C. Haddon, J. Am. Chem. Soc., 2002, 124, 8090.

    Article  CAS  Google Scholar 

  22. A. R. Tuktarov, U. M. Dzhemilev, Russ. Chem. Rev., 2010, 79, 585.

    Article  CAS  Google Scholar 

  23. J. C. Jameson, Annu. Rev. Phys. Chem., 1996, 47, 135.

    Article  CAS  Google Scholar 

  24. W. Andreoni, Annu. Rev. Phys. Chem., 1998, 49, 405.

    Article  CAS  Google Scholar 

  25. L. M. Khalilov, A. R. Tulyabaev, A. R. Tuktarov, Magn. Reson. Chem., 2011, 49, 768.

    Article  CAS  Google Scholar 

  26. A. R. Tulyabaev, A. R. Tuktarov, L. M. Khalilov, Magn. Reson. Chem., 2014, 52, 3.

    Article  CAS  Google Scholar 

  27. J. P. Perdew, K. Burke, M. Ernzerhof, Phys. Rev. Lett., 1996, 77, 3865.

    Article  CAS  Google Scholar 

  28. D. N. Laikov, Chem. Phys. Lett., 1997, 281, 151.

    Article  CAS  Google Scholar 

  29. D. N. Laikov, Yu. A. Ustynyuk, Russ. Chem. Bull. (Int. Ed.) 2005, 54, 820 [Izv. Akad. Nauk, Ser. Khim., 2005, 804].

    Article  CAS  Google Scholar 

  30. D. N. Laikov, PhD Thesis (Chem.), Moscow State Univ., Moscow, 2000, 103 pp.

    Google Scholar 

  31. A. R. Tulyabaev, L. M. Khalilov, Comput. Theor. Chem., 2011, 976, 12.

    Article  CAS  Google Scholar 

  32. E. Y. Pankratyev, A. R. Tulyabaev, L. M. Khalilov, J. Comput. Chem., 2011, 32, 1993.

    Article  CAS  Google Scholar 

  33. S. K. Wolff, T. Ziegler, J. Chem. Phys., 1998, 109, 895.

    Article  CAS  Google Scholar 

  34. T. Heine, G. Seifert, P. W. Fowler, F. Zerbetto J. Phys. Chem. A, 1999, 103, 8738.

    Article  CAS  Google Scholar 

  35. W. H. Powell, F. Cozzi, G. P. Moss, C. Thilgen, R. J.-R. Hwu, A. Yerin, Pure Appl. Chem., 2002, 74, 629.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, 141 prosp. Oktyabrya, 450075, Ufa, Russian Federation

    M. Khalilov, A. R. Tulyabaev, A. R. Akhmetov & A. R. Tuktarov

Authors
  1. M. Khalilov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. R. Tulyabaev
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. R. Akhmetov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. R. Tuktarov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. R. Tulyabaev.

Additional information

Based on the materials of the International Conference Molecular Complexity in Modern Chemistry (MCMC-2014) (September 13—19, 2014, Moscow, Russia).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2725—2730, November, 2015.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Khalilov, M., Tulyabaev, A.R., Akhmetov, A.R. et al. Synthesis and 13C NMR features of N-substituted aziridino[60]fullerenes. Russ Chem Bull 64, 2725–2730 (2015). https://doi.org/10.1007/s11172-015-1214-x

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-015-1214-x

Key words

Search

Navigation