Unexpected formation of a Sc 3C 2@C 80 bisfulleroid derivative

Journal of the American Chemical Society

Volumn 134, Issue 9, 2012, Pages 4092-4095

  Kurihara, Hiroki ^a   Iiduka, Yuto ^a   Rubin, Yves ^b   Waelchli, Markus ^c   Mizorogi, Naomi ^a   Slanina, Zdenek ^a   Tsuchiya, Takahiro ^a   Nagase, Shigeru ^d   Akasaka, Takeshi ^a  

^a UNIVERSITY OF TSUKUBA   (Japan)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c Bruker Corporation   (United States)

^d INSTITUTE FOR MOLECULAR SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EPR SPECTROSCOPY; FOUR-MEMBERED RINGS; METAL ATOMS; TETRAZINES; THEORETICAL CALCULATIONS;

NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

SCANDIUM;

BISFULLEROID DERIVATIVE; FULLERENE DERIVATIVE; METAL; UNCLASSIFIED DRUG; CARBON; SCANDIUM; TETRAZOLE DERIVATIVE;

ARTICLE; ATOM; CHEMICAL STRUCTURE; ELECTRON SPIN RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; CHEMISTRY;

CARBON; MODELS, MOLECULAR; MOLECULAR STRUCTURE; SCANDIUM; TETRAZOLES;

EID: 84857878916     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja300279x     Document Type: Article

References (47)

1. Hirsch, A. The Chemistry of the Fullerenes; Wiley-VCH, Weinheim, Germany, 2005.
2. Endofullerenes: A New Family of Carbon Clusters; Akasaka, T., Nagase, S., Eds.; Kluwer: Dordrecht, The Netherlands, 2002.
3. (a) Hummelen, J. C.; Knight, B.; Pavlovich, J.; González, R.; Wudl, F. Science 1995, 269, 1554.
4. (b) Nuber, B.; Hirsch, A. Chem. Commun. 1996, 1421.
5. (c) Vostrowsky, O.; Hirsch, A. Chem. Rev. 2006, 106, 5191.
6. (a) Qian, W.; Chuang, S.-C.; Amador, R. B.; Jarrosson, T.; Sander, M.; Pieniazek, S.; Khan, S. I.; Rubin, Y. J. Am. Chem. Soc. 2003, 125, 2066.
7. (b) Ioffe, I.; Chen, C.; Yang, S.; Sidorov, L.; Kemnitz, E.; Troyanov, S. Angew. Chem., Int. Ed. 2010, 49, 4784.
8. (a) Rubin, Y.; Jarrosson, T.; Wang, G.-W.; Bartberger, M. D.; Schick, G.; Saunders, M.; Cross, R. J.; Houk, K. N. Angew. Chem., Int. Ed. 2001, 40, 1543.
9. (b) Murata, M.; Murata, Y.; Komatsu, K. Chem. Commun. 2008, 6083.
10. (c) Murata, Y.; Murata, M.; Komatsu, K. J. Am. Chem. Soc. 2003, 125, 7152.
11. (d) Murata, Y.; Murata, M.; Komatsu, K. Chem.-Eur. J. 2003, 9, 1600.
12. (e) Yu, Y.; Xie, X.; Zhang, T.; Liu, S.; Shao, Y.; Gan, L.; Li, Y. J. Org. Chem. 2011, 76, 10148.
13. (f) Iwamatsu, S.; Uozaki, T.; Kobayashi, K.; Re, S.; Nagase, S.; Murata, S. J. Am. Chem. Soc. 2004, 126, 2668.
14. (g) Whitener, K. E. Jr.; Frunzi, M.; Iwamatsu, S.; Murata, S. R.; Cross, J.; Saunders, M. J. Am. Chem. Soc. 2008, 130, 13996.
15. (h) Gan, L.; Yang, D.; Zhang, Q.; Huang, H. Adv. Mater. 2010, 22, 1498.
16. (i) Vougioukalakis, G. C.; Roubelakis, M. M.; Orfanopoulos, M. Chem. Soc. Rev. 2010, 39, 817.
17. (a) Komatsu, K.; Murata, M.; Murata, Y. Science 2005, 307, 238.
18. (b) Kurotobi, K.; Murata, Y. Science 2011, 333, 613.
19. (a) Chemistry of Nanocarbons; Akasaka, T., Wudl, F., Nagase, S., Eds.; Wiley: Chichester, U.K., 2010.
20. (b) Dunsch, L.; Yang, S. Small 2007, 3, 1298.
21. (c) Chaur, M. N.; Melin, F.; Ortiz, A. L.; Echegoyen, L. Angew. Chem., Int. Ed. 2009, 48, 7514.
22. (d) Yamada, M.; Akasaka, T.; Nagase, S. Acc. Chem. Res. 2010, 43, 92.
23. (e) Osuna, S.; Swart, M.; Solà, M. Phys. Chem. Chem. Phys. 2011, 13, 3585.
24. Iiduka, Y.; Wakahara, T.; Nakahodo, T.; Tsuchiya, T.; Sakuraba, A.; Maeda, Y.; Akasaka, T.; Yoza, K.; Horn, E.; Kato, T.; Liu, M. T. H.; Mizorogi, N.; Kobayashi, K.; Nagase, S. J. Am. Chem. Soc. 2005, 127, 12500.
25. See the Supporting Information.
26. (a) Lu, X.; Nikawa, H.; Tsuchiya, T.; Akasaka, T.; Toki, M.; Sawa, H.; Mizorogi, N.; Nagase, S. Angew. Chem., Int. Ed. 2010, 49, 594.
27. (b) Lu, X.; Nikawa, H.; Kikuchi, T.; Mizorogi, N.; Slanina, Z.; Tsuchiya, T.; Nagase, S.; Akasaka, T. Angew. Chem., Int. Ed. 2011, 50, 6356.
28. (a) Fagan, P. J.; Krusic, P. J.; Evans, D. H.; Lerke, S. A.; Johnston, E. J. Am. Chem. Soc. 1992, 114, 9697.
29. (b) Anderson, H. L.; Faust, R.; Rubin, Y.; Diederich, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 1366.
30. (c) Matsuo, Y.; Iwashita, A.; Abe, Y.; Li, C.-Z.; Matsuo, K.; Hashiguchi, M.; Nakamura, E. J. Am. Chem. Soc. 2008, 130, 15429.
31. (a) Becke, A. D. Phys. Rev. A 1988, 38, 3098.
32. (b) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
33. (c) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
34. (a) Binkley, J. S.; Pople, J. A.; Hehre, W. J. J. Am. Chem. Soc. 1980, 102, 939.
35. (b) Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299.
36. (c) Francl, M. M.; Pietro, W. J.; Hehre, W. J.; Binkley, J. S.; DeFrees, D. J.; Pople, J. A.; Gordon, M. S. J. Chem. Phys. 1982, 77, 3654.
37. (d) Cao, X. Y.; Dolg, M. THEOCHEM 2002, 581, 139.
38. (e) Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650.
39. (f) Wiberg, K. B. Tetrahedron 1968, 24, 1083.
40. (g) Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. J. Chem. Phys. 1985, 83, 735.
41. Frisch, M. J. et al.; Gaussian 09, revision A.02; Gaussian, Inc.: Wallingford, CT, 2009.
42. (a) Iezzi, E. B.; Duchamp, J. C.; Harich, K.; Glass, T. E.; Lee, H. M.; Olmstead, M. M.; Balch, A. L.; Dorn, H. C. J. Am. Chem. Soc. 2002, 124, 524.
43. (b) Lee, H. M.; Olmstead, M. M.; Iezzi, E.; Duchamp, J. C.; Dorn, H. C.; Balch, A. L. J. Am. Chem. Soc. 2002, 124, 3494.
44. Cyrański, M. K.; Howard, S. T.; Chodkiewicz, M. L. Chem. Commun. 2004, 2458.
45. For recent record C-C bond lengths in sterically crowded molecules and related background, see: Schreiner, P. R.; Chernish, L. V.; Gunchenko, P. A.; Tikhonchuk, E. Y.; Hausmann, H.; Serafin, M.; Schlecht, S.; Dahl, J. E. P.; Carlson, R. M. K.; Fokin, A. A. Nature 2011, 477, 308.
46. Shinohara, H.; Inakuma, M.; Hayashi, N.; Sato, H.; Saito, Y.; Kato, T.; Bandow, S. J. Phys. Chem. 1994, 98, 8597.
47. Wang, T.; Wu, J.; Xu, W.; Xiang, J.; Lu, X.; Li, B.; Jiang, L.; Shu, C.; Wang, C. Angew. Chem., Int. Ed. 2010, 49, 1786.