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New isomers of trifluoromethylated fullerene: C60(CF3)12 and C60(CF3)14

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Abstract

HPLC separation of the products of high-temperature reaction of a sublimed mixture of C60–C70 (10: 1) with CF3I in a sealed ampoule allowed isolation and determination of molecular structures (X-ray crystallography and 19F NMR) of two new isomers of C60(CF3)12 and one isomer of C60(CF3)14. These isomers are characterized by low relative formation energies, which suggests that the trifluoromethylation process is basically under the thermodynamic control.

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References

  1. P. J. Fagan, P. J. Krusic, C. N. McEwen, J. Lazar, D. H. Parker, N. Herron, E. Wasserman, Science, 1993, 262, 404.

    Article  CAS  Google Scholar 

  2. I. S. Uzkikh, E. I. Dorozhkin, O. V. Boltalina, A. I. Boltalin, Dokl. Akad. Nauk, 2001, 379, 344 [Dokl. Chem., 2001, 379, 204 (Engl. Transl.)].

    CAS  Google Scholar 

  3. A. A. Goryunkov, I. V. Kuvychko, I. N. Ioffe, D. L. Dick, L. N. Sidorov, S. H. Strauss, O. V. Boltalina, J. Fluorine Chem., 2003, 124, 61.

    Article  CAS  Google Scholar 

  4. E. I. Dorozhkin, A. A. Goryunkov, I. N. Ioffe, S. M. Avdoshenko, V. Yu. Markov, N. B. Tamm, D. V. Ignatéva, L. N. Sidorov, S. I. Troyanov, Eur. J. Org. Chem., 2007, 5082.

  5. I. E. Kareev, I. V. Kuvychko, S. F. Lebedkin, S. M. Miller, O. P. Anderson, K. Seppelt, S. H. Strauss, O. V. Boltalina, J. Am. Chem. Soc., 2005, 127, 8362.

    Article  CAS  Google Scholar 

  6. S. I. Troyanov, A. Dimitrov, E. Kemnitz, Angew. Chem., nt. Ed., 2006, 45, 1971.

    Article  CAS  Google Scholar 

  7. S. I. Troyanov, A. A. Goryunkov, E. I. Dorozhkin, D. V. Ignat’eva, N. B. Tamm, S. M. Avdoshenko, I. N. Ioffe, V. Yu. Markov, L. N. Sidorov, K. Scheurel, E. Kemnitz, J. Fluorine Chem., 2007, 128, 545.

    Article  CAS  Google Scholar 

  8. A. A. Popov, I. E. Kareev, N. B. Shustova, S. F. Lebedkin, S. H. Strauss, O. V. Boltalina, L. Dunsch, Chem. Eur. J., 2008, 14, 107.

    Article  CAS  Google Scholar 

  9. I. E. Kareev, N. B. Shustova, I. V. Kuvychko, S. F. Lebedkin, S. M. Miller, O. P. Anderson, A. A. Popov, S. H. Strauss, O. V. Boltalina, J. Am. Chem. Soc., 2006, 128, 12268.

    Article  CAS  Google Scholar 

  10. I. E. Kareev, N. B. Shustova, B. S. Newell, S. M. Miller, O. P. Anderson, S. H. Strauss, O. V. Boltalina, Acta Crystallogr., Sect. E, 2006, 62, o3154.

    Article  Google Scholar 

  11. A. A. Goryunkov, E. I. Dorozhkin, N. B. Tamm, D. V. Ignatéva, S. M. Avdoshenko, L. N. Sidorov, S. I. Troyanov, Mendeleev Commun., 2007, 17, 110.

    Article  CAS  Google Scholar 

  12. N. B. Shustova, D. V. Peryshkov, I. E. Kareev, O. V. Boltalina, S. H. Strauss, Acta Crystallogr., Sect. E, 2007, 63, o3398.

    Article  Google Scholar 

  13. (a) I. E. Kareev, S. F. Lebedkin, S. M. Miller, O. P. Anderson, S. H. Strauss, O. V. Boltalina, Acta Crystallogr., Sect. E, 2006, 62, o1498

    Google Scholar 

  14. I. E. Kareev, S. F. Lebedkin, A. A. Popov, S. M. Miller, O. P. Anderson, S. H. Strauss, O. V. Boltalina, Acta Crystallogr., Sect. E, 2006, 62, o1501

    Article  Google Scholar 

  15. A. A. Popov, I. E. Kareev, N. B. Shustova, E. B. Stukalin, S. F. Lebedkin, K. Seppelt, S. H. Strauss, O. V. Boltalina, L. Dunsch, J. Am. Chem. Soc., 2007, 129, 11551.

    Article  CAS  Google Scholar 

  16. N. A. Omelyanyuk, A. A. Goryunkov, N. B. Tamm, S. M. Avdoshenko, I. N. Ioffe, L. N. Sidorov, E. Kemnitz, S. I. Troyanov, Chem. Commun., 2007, 4794.

  17. (a) I. E. Kareev, N. B. Shustova, D. V. Peryshkov, S. F. Lebedkin, S. M. Miller, O. P. Anderson, A. A. Popov, O. V. Boltalina, S. H. Strauss, Chem. Commun., 2007, 1650

  18. N. B. Shustova, O. P. Anderson, O. V. Boltalina, S. H. Strauss, I. E. Kareev, Acta Crystallogr., Sect. E, 2008, 64, o159.

    Article  Google Scholar 

  19. G. M. Sheldrick, SHELXS-97, Program for Solution of Crystal Structures from Diffraction Data, Göttingen Universität, Göttingen, Germany, 1997.

  20. G. M. Sheldrick, SHELXL97. Program for Crystal Structure Refinement, Göttingen Universität, Göttingen, Germany, 1997.

    Google Scholar 

  21. A. A. Granovsky, http://classic.chem.msu.su/gran/gamess/index.html; M. W. Schmidt, K. K. Baldridge, J. A. Boatz, S. T. Elbert, M. S. Gordon, J. J. Jensen, S. Koseki, N. Mat- sunaga, K. A. Nguyen, S. Su, T. L. Windus, M. Dupuis, J. A. Montgomery, J. Comput. Chem., 1993, 14, 1347.

    Article  Google Scholar 

  22. D. Laikov, Chem. Phys. Lett., 1997, 281, 151.

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  24. E. V. Skokan, V. I. Privalov, I. V. Arkhangelśkii, V. Ya. Davydov, N. B. Tamm, J. Phys. Chem. B, 1999, 103, 2050.

    Article  CAS  Google Scholar 

  25. T. Mutig, I. N. Ioffe, E. Kemnitz, S. I. Troyanov, Mendeleev Commun., 2008, 18, 73.

    Article  CAS  Google Scholar 

  26. F. Cozzi, W. H. Powell, C. Thilgen, Pure Appl. Chem., 2005, 77, 843.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, M. V. Lomonosov Moscow State University, 1 Leninskie Gory, 119991, Moscow, Russian Federation

    N. A. Samokhvalova, P. A. Khavrel’, A. A. Goryunkov, I. N. Ioffe, L. N. Sidorov & S. I. Troyanova

  2. Fullerene Center, 4 ul. Kostina, 603000, Nizhny Novgorod, Russian Federation

    V. L. Karnatsevich

  3. Institute of Chemistry, Humboldt University Berlin, 2 Brook-Taylor-Str., 12489, Berlin, Germany

    E. Kemnitz

Authors
  1. N. A. Samokhvalova
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  2. P. A. Khavrel’
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  3. A. A. Goryunkov
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  4. I. N. Ioffe
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  5. V. L. Karnatsevich
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  6. L. N. Sidorov
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  7. E. Kemnitz
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  8. S. I. Troyanova
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Correspondence to S. I. Troyanova.

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Humboldt-Universität zu Berlin, Institut für Chemie, Brook-Taylor-Str. 2, 12489 Berlin, Deutschland.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2475–2483, December, 2008.

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Samokhvalova, N.A., Khavrel’, P.A., Goryunkov, A.A. et al. New isomers of trifluoromethylated fullerene: C60(CF3)12 and C60(CF3)14 . Russ Chem Bull 57, 2526–2534 (2008). https://doi.org/10.1007/s11172-008-0363-6

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  • DOI: https://doi.org/10.1007/s11172-008-0363-6

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