Internal magnetic fields of dianions of fullerene C60 and its cage-opened derivatives studied with encapsulated H2 as an NMR probe

Angewandte Chemie - International Edition

Volumn 47, Issue 11, 2008, Pages 2039-2041

  Murata, Michihisa ^b   Ochi, Yuta ^b   Tanabe, Fumiyuki ^b   Komatsu, Koichi ^a   Murata, Yasujiro ^b  

^a FUKUI UNIVERSITY OF TECHNOLOGY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

Aromaticity; Density functional calculations; Fullerenes; NMR spectroscopy; Ring currents

Indexed keywords

FULLERENES; MAGNETIC FIELDS; NUCLEAR MAGNETIC RESONANCE;

AROMATICITY; DENSITY FUNCTIONAL CALCULATIONS; NMR SPECTROSCOPY; RING CURRENTS;

HYDROGEN;

ANION; FULLERENE C60; FULLERENE DERIVATIVE; HYDROGEN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODEL; CHEMISTRY; MAGNETISM; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SENSITIVITY AND SPECIFICITY; STANDARD;

ANIONS; FULLERENES; HYDROGEN; MAGNETIC RESONANCE SPECTROSCOPY; MAGNETICS; MODELS, CHEMICAL; REFERENCE STANDARDS; SENSITIVITY AND SPECIFICITY;

EID: 41949105745     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200705285     Document Type: Article

References (38)

1. a) V. Elser, R. C. Haddon, Nature 1987, 325, 792-794;
2. b) A. Pasquarello, M. Schlüter, R. C. Haddon, Science 1992, 257, 1660-1661;
3. c) R. C. Haddon, Science 1993, 261, 1545-1550;
4. d) A. Pasquarello, M. Schlüter, R. C. Haddon, Phys. Rev. A 1993, 47, 1783-1789;
5. e) M. Bühl, Chem. Eur. J. 1998, 4, 734-739;
6. f) A. Hirsch, Z. Chen, H. Jiao, Angew. Chem. 2000, 112, 4079-4081;
7. Angew. Chem. Int. Ed. 2000, 39, 3915-3917;
8. g) M. Bühl, A. Hirsch, Chem. Rev. 2001, 101, 1153-1183.
9. M. Saunders, R. J. Cross, H. A. Jiménez-Vázquez, R. Shimshi, A. Khong, Science 1996, 271, 1693-1697.
10. a) M. Saunders, H. A. Jiménez-Vázquez, B. W. Bangerter, R. J. Cross, J. Am. Chem. Soc. 1994, 116, 3621-3622;
11. b) A. B. Smith III, R. M. Strongin, L. Brard, W. J. Romanow, M. Saunders, H. A. Jiménez-Vázquez, R. J. Cross, J. Am. Chem. Soc. 1994, 116, 10831-10832;
12. c) M. Rüttimann, R. F. Haldimann, L. Isaacs, F. Diederich, A. Khong, H. A. Jiménez-Vázquez, R. J. Cross, M. Saunders, Chem. Eur. J. 1997, 3, 1071-1076;
13. d) O. V. Boltalina, M. Bühl, A. Khong, M. Saunders, J. M. Street, R. Taylor, J. Chem. Soc. Perkin Trans. 2 1999, 1475-1479.
14. a) E. Shabtai, A. Weitz, R. C. Haddon, R. E. Hoffman, M. Rabinovitz, A. Khong, R. J. Cross, M. Saunders, P.-C. Cheng, L. T. Scott, J. Am. Chem. Soc. 1998, 120, 6389-6393;
15. b) T. Sternfeld, F. Wudl, K. Hummelen, A. Weizt, R. C. Haddon, M. Rabinovitz, Chem. Commun. 1999, 2037-2039;
16. c) T. Sternfeld, R. E. Hoffman, M. Saunders, R. J. Cross, S. Syamala, M. Rabinovitz, J. Am. Chem. Soc. 2002, 124, 8786-8787.
17. a) R. Subramanian, K. M. Kadish, M. N. Vijayashree, X. Gao, M. T. Jones, J. Phys. Chem. 1996, 100, 16327-16335;
18. b) S. Fukuzumi, T. Suenobu, T. Hirasaka, R. Arakawa, K. M. Kadish, J. Am. Chem. Soc. 1998, 120, 9220-9227;
19. c) Y.-H. Zhu, L.-C. Song, Q.-M. Hu, C.-M. Li, Org. Lett. 1999, 1, 1693-1695.
20. a) E. Allard, L. Riviere, J. Delaunay, D. Dubois, J. Cousseau, Tetrahedron Lett. 1999, 40, 7223-7226;
21. b) E. Allard, J. Delaunay, F. Cheng, J. Cousseau, J. Ordúna, G. Javier, Org. Lett. 2001, 3, 3503-3506;
22. c) F. Cheng, Y. Murata, K. Komatsu, Org. Lett. 2002, 4, 2541-2544.
23. P. C. Trulove, R. T. Carlin, G. R. Eaton, S. S. Eaton, J. Am. Chem. Soc. 1995, 117, 6265-6272.
24. a) Y. Murata, M. Murata, K. Komatsu, Chem. Eur. J. 2003, 9, 1600-1609;
25. b) Y. Murata, M. Murata, K. Komatsu, J. Am. Chem. Soc. 2003, 125, 7152-7153;
26. c) K. Komatsu, M. Murata, Y. Murata, Science 2005, 307, 238-240;
27. d) K. Komatsu, Y. Murata, Chem. Lett. 2005, 34, 886-891.
28. M. Murata, Y. Murata, K. Komatsu, J. Am. Chem. Soc. 2006, 128, 8024-8033.
29. R. Subramanian, P. Boulas, M. N. Vijayashree, F. D'Souza, M. T. Jones, K. M. Kadish, J. Chem. Soc. Chem. Commun. 1994, 1847-1848.
30. P. D. W. Boyd, P. Bhyrappa, P. Paul, J. Stinchcombe, R. D. Bolskar, Y. Sun, C. A. Reed, J. Am. Chem. Soc. 1995, 117, 2907-2914.
31. a) Y. Matsuo, H. Isobe, T. Tanaka, Y. Murata, M. Murata, K. Komatsu, E. Nakamura, J. Am. Chem. Soc. 2005, 127, 17148-17149;
32. b) Y. Rubin, T. Jarrosson, G.-W. Wang, M. D. Bartberger, K. N. Houk, G. Schick, M. Saunders, R. J. Cross, Angew. Chem. 2001, 113, 1591-1594;
33. Angew. Chem. Int. Ed. 2001, 40, 1543-1546;
34. c) S.-i. Iwamatsu, S. Murata, Y. Andoh, M. Minoura, K. Kobayashi, N. Mizorogi, S. Nagase, J. Org. Chem. 2005, 70, 4820-4825.
35. K. Wolinski, J. F. Hinton, P. Pulay, J. Am. Chem. Soc. 1990, 112, 8251-8260.
36. Gaussian03 (Revision D.02): M. J. Frisch et al., see the Supporting Information.
37. P. v. R. Schleyer, C. Maerker, A. Dransfeld, H. Jiao, N. J. R. v. E. Hommes, J. Am. Chem. Soc. 1996, 118, 6317-6318.
38. [11] although the possibility of formation of radical trianions cannot be rigorously ruled out.