The First Crystal Structure of a Halogenated Higher Fullerene, C 78Br18, Obtained by Bromination of a Fullerene Mixture

European Journal of Organic Chemistry

Volumn , Issue 20, 2003, Pages 3916-3919

  Troyanov, Sergey I ^a   Kemnitz, Erhard ^b  

^a MOSCOW STATE UNIVERSITY   (Russian Federation)

^b HUMBOLDT UNIVERSITY   (Germany)

Author keywords

Bromination; C78; Crystal structure; Higher fullerenes

Indexed keywords

BROMINE; CARBON; FULLERENE DERIVATIVE;

ARTICLE; ATOM; BROMINATION; CHEMICAL BINDING; CRYSTAL STRUCTURE; CRYSTALLIZATION; HALOGENATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMERISM; PRECIPITATION; X RAY CRYSTALLOGRAPHY;

EID: 0242291967     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200300358     Document Type: Article

References (33)

1. K. Kikuchi, N. Nakahara, T. Wakabayashi, S. Suzuki, K. Saito, I. Ikemoto, Y. Achiba, Synth. Met. 1993, 56, 3208-3213.
2. J. M. Hawkins, M. Nambu, A. Meyer, J. Am. Chem. Soc. 1994, 116, 7642-7645; C. Thilgen, A. Herrmann, F. Diederich, Angew. Chem. Int. Ed. 1997, 36, 2268-2280; Angew. Chem. 1997, 109, 2362-2374.
3. J. M. Hawkins, M. Nambu, A. Meyer, J. Am. Chem. Soc. 1994, 116, 7642-7645; C. Thilgen, A. Herrmann, F. Diederich, Angew. Chem. Int. Ed. 1997, 36, 2268-2280; Angew. Chem. 1997, 109, 2362-2374.
4. J. M. Hawkins, M. Nambu, A. Meyer, J. Am. Chem. Soc. 1994, 116, 7642-7645; C. Thilgen, A. Herrmann, F. Diederich, Angew. Chem. Int. Ed. 1997, 36, 2268-2280; Angew. Chem. 1997, 109, 2362-2374.
5. A. G. Avent, B. W. Clare, P. B. Hitchcock, D. L. Kepert, R. Taylor, J. Chem. Soc., Chem. Commun. 2002, 2370-2371; R. Taylor, Chem. Eur. J. 2002, 7, 4075-4083.
6. A. G. Avent, B. W. Clare, P. B. Hitchcock, D. L. Kepert, R. Taylor, J. Chem. Soc., Chem. Commun. 2002, 2370-2371; R. Taylor, Chem. Eur. J. 2002, 7, 4075-4083.
7. P. R. Birkett, A. G. Avent, A. D. Darwish, H. W. Kroto, R. Taylor, D. R. M. Walton, J. Chem. Soc., Chem. Commun. 1993, 1230-1233.
8. P. R. Birkett, P. B. Hitchcock, H. W. Kroto, R. Taylor, D. R. M. Walton, Nature 1992, 357, 479-481; F. N. Tebbe, R. L. Harlow, D. B. Chase, D. L. Thorn, G. C. Campbell, J. C. Calabrese, N. Herron, R. J. Young, E. Wasserman, Science 1992, 256, 822-825; P. A. Troshin, D. Kolesnikov, A. V. Burtsev, R. N. Lubovskaya, N. I. Denisenko, A. A. Popov, S. I. Troyanov, O. V. Boltalina, Fullerenes Nanotubes Carbon Nanostruct. 2003, 11, 47-60.
9. P. R. Birkett, P. B. Hitchcock, H. W. Kroto, R. Taylor, D. R. M. Walton, Nature 1992, 357, 479-481; F. N. Tebbe, R. L. Harlow, D. B. Chase, D. L. Thorn, G. C. Campbell, J. C. Calabrese, N. Herron, R. J. Young, E. Wasserman, Science 1992, 256, 822-825; P. A. Troshin, D. Kolesnikov, A. V. Burtsev, R. N. Lubovskaya, N. I. Denisenko, A. A. Popov, S. I. Troyanov, O. V. Boltalina, Fullerenes Nanotubes Carbon Nanostruct. 2003, 11, 47-60.
10. P. R. Birkett, P. B. Hitchcock, H. W. Kroto, R. Taylor, D. R. M. Walton, Nature 1992, 357, 479-481; F. N. Tebbe, R. L. Harlow, D. B. Chase, D. L. Thorn, G. C. Campbell, J. C. Calabrese, N. Herron, R. J. Young, E. Wasserman, Science 1992, 256, 822-825; P. A. Troshin, D. Kolesnikov, A. V. Burtsev, R. N. Lubovskaya, N. I. Denisenko, A. A. Popov, S. I. Troyanov, O. V. Boltalina, Fullerenes Nanotubes Carbon Nanostruct. 2003, 11, 47-60.
11. R. Taylor, A. K. Abdul-Sada, O. V. Boltalina, J. M. Street, J. Chem. Soc., Perkin Trans. 2 2000, 1013-1021.
12. P. R. Birkett, A. G. Avent, A. D. Darwish, H. W. Kroto, R. Taylor, D. R. M. Walton, J. Chem. Soc., Chem. Commun. 1995, 683-684.
13. G. Waidmann, M. Jansen, Z. Anorg. Allg. Chem. 1997, 623, 623-626.
14. N. I. Denisenko, A. A. Popov, I. V. Kuvychko, O. V. Boltalina, N. V. Chelovskaya, Proc. - Electrochem. Soc. 2002, 12, 577-586; S. I. Troyanov, A. A. Popov, N. I. Denisenko, L. N. Sidorov, O. V. Boltalina, E. Kemnitz, Angew. Chem. Int. Ed. 2003, 42, 2395-2398; Angew. Chem. 2003, 115, 2497-2500.
15. N. I. Denisenko, A. A. Popov, I. V. Kuvychko, O. V. Boltalina, N. V. Chelovskaya, Proc. - Electrochem. Soc. 2002, 12, 577-586; S. I. Troyanov, A. A. Popov, N. I. Denisenko, L. N. Sidorov, O. V. Boltalina, E. Kemnitz, Angew. Chem. Int. Ed. 2003, 42, 2395-2398; Angew. Chem. 2003, 115, 2497-2500.
16. N. I. Denisenko, A. A. Popov, I. V. Kuvychko, O. V. Boltalina, N. V. Chelovskaya, Proc. - Electrochem. Soc. 2002, 12, 577-586; S. I. Troyanov, A. A. Popov, N. I. Denisenko, L. N. Sidorov, O. V. Boltalina, E. Kemnitz, Angew. Chem. Int. Ed. 2003, 42, 2395-2398; Angew. Chem. 2003, 115, 2497-2500.
17. A. K. Abdul-Sada, T. V. Avakyan, O. V. Boltalina, V. Yu. Markov, J. M. Street, R. Taylor, J. Chem. Soc., Perkin Trans. 2 1999, 2659-2666; O. V. Boltalina, T. V. Avakyan, V. Yu. Markov, T. J. S. Dennis, A. K. Abdul-Sada, R. Taylor, J. Phys. Chem. B 1999, 103, 8189-8191.
18. A. K. Abdul-Sada, T. V. Avakyan, O. V. Boltalina, V. Yu. Markov, J. M. Street, R. Taylor, J. Chem. Soc., Perkin Trans. 2 1999, 2659-2666; O. V. Boltalina, T. V. Avakyan, V. Yu. Markov, T. J. S. Dennis, A. K. Abdul-Sada, R. Taylor, J. Phys. Chem. B 1999, 103, 8189-8191.
19. 2 or HBr molecules are most likely present. EDX analysis of the crystals weathered during ca. 4 months showed the presence of ca. 1 mol-% S (less, than expected). The larger disordered region contains a highly disordered nonidentified molecule of solvation. CCDC-210174 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: (internat.) + 44-1223/336-033; E-mail: deposit@ccdc.cam.ac.uk].
20. P. W. Fowler, R. C. Batten, D. E. Manolopoulos, J. Chem. Soc., Faraday Trans. 1991, 87, 3103-3104; F. Uhlík, Zd. Slanina, E. Osawa, Eur. Phys. J. D 2001, 16, 349-352.
21. P. W. Fowler, R. C. Batten, D. E. Manolopoulos, J. Chem. Soc., Faraday Trans. 1991, 87, 3103-3104; F. Uhlík, Zd. Slanina, E. Osawa, Eur. Phys. J. D 2001, 16, 349-352.
22. K. Kikuchi N. Nakahara, T. Wakabayashi, S. Suzuki, H. Shiromaru, Y. Miyake, K. Saito, I. Ikemoto, M. Kainosho, Y. Achiba, Nature 1992, 357, 142-145.
23. R. Taylor, G. J. Langley, A. G. Avent, T. J. S. Dennis, H. W. Kroto, D. R. M. Walton, J. Chem. Soc., Perkin Trans. 2 1993, 1029-1036.
24. F. Diederich, R. L. Whetten, C. Thilgen, R. Ettl, I. Chao, M. M. Alvarez, Science 1991, 254, 1768-1770.
25. M. M. Olmstead, A. Bettencourt-Dias, J. C. Duchamp, S. Stevenson, D. Marciu, H. C. Dorn, A. L. Balch, Angew. Chem. Int. Ed. 2001, 40, 1223-1225; Angew. Chem. 2001, 113, 1263-1265; J. M. Campanera, C. Bo, M. M. Olmstead, A. L. Balch, J. M. Poblet, J. Phys. Chem. A, 2002, 106, 12356-12364.
26. M. M. Olmstead, A. Bettencourt-Dias, J. C. Duchamp, S. Stevenson, D. Marciu, H. C. Dorn, A. L. Balch, Angew. Chem. Int. Ed. 2001, 40, 1223-1225; Angew. Chem. 2001, 113, 1263-1265; J. M. Campanera, C. Bo, M. M. Olmstead, A. L. Balch, J. M. Poblet, J. Phys. Chem. A, 2002, 106, 12356-12364.
27. M. M. Olmstead, A. Bettencourt-Dias, J. C. Duchamp, S. Stevenson, D. Marciu, H. C. Dorn, A. L. Balch, Angew. Chem. Int. Ed. 2001, 40, 1223-1225; Angew. Chem. 2001, 113, 1263-1265; J. M. Campanera, C. Bo, M. M. Olmstead, A. L. Balch, J. M. Poblet, J. Phys. Chem. A, 2002, 106, 12356-12364.
28. A. L. Balch, A. S. Ginwalla, J. W. Lee, B. C. Noll, M. M. Olmstead, J. Am. Chem. Soc 1994, 116, 2227-2228.
29. D. N. Laikov, Chem. Phys. Lett. 1997, 281, 151-156.
30. S. I. Troyanov, P. A. Troshin, O. V. Boltalina, E. Kemnitz, Fullerenes Nanotubes Carbon Nanostruct. 2003, 11, 61-77.
31. A. Han, T. Wakahara, Y. Maeda, Y. Niino, T. Akasaka, K. Yamamoto, M. Kako, Y. Nakadaira, K. Kobayashi, S. Nagase, Chem. Lett. 2001, 974-975.
32. R. Taylor, J. Chem. Soc, Perkin Trans. 2 1992, 1667-1669.
33. R. Taylor, J. Chem. Soc., Perkin Trans. 2 1993, 813-824.