π-Arene/cation structure and bonding. Solvation versus ligand binding in iron(III) tetraphenylporphyrin complexes of benzene, toluene, p-xylene, and [60]fullerene

Journal of the American Chemical Society

Volumn 121, Issue 37, 1999, Pages 8466-8474

  Evans, Daniel R ^a   Fackler, Nathanael L P ^b   Xie, Zuowei ^a   Rickard, Clifton E F ^b   Boyd, Peter D W ^b   Reed, Christopher A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF AUCKLAND   (New Zealand)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALI METAL; BENZENE; CATION; FERRIC ION; FULLERENE; METALLOPORPHYRIN; PARA XYLENE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SOLVENT; TETRAPHENYLPORPHYRIN; TOLUENE;

ARTICLE; CHEMICAL BINDING; CHEMICAL STRUCTURE; COMPLEX FORMATION; COVALENT BOND; CRYSTALLIZATION; LIGAND BINDING; MOLECULAR INTERACTION; SOLVATION; THEORY;

EID: 0033595559     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9910816     Document Type: Article

References (66)

1. Chem. Eur. J. 1998, 4, 1349-1383 (special issue on supramolecular chemistry).
2. Desiraju, G. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 2311.
3. Scudder, M.; Dance, I. J. Chem. Soc., Dalton Trans. 1998, 3155.
4. Burley, S. K.; Petsko, G. A. Adv. Protein Chem. 1988, 39, 125.
5. Ma, J. C.; Dougherty, D. A. Chem. Rev. 1997, 97, 1303.
6. Eisch, J. J.; Pombrik, S. I.; Zheng, G.-X. Organometallics 1993, 12, 3856.
7. Mecozzi, S.; West, A. P., Jr.; Dougherty, D. A. J. Am. Chem. Soc. 1996, 118, 2307.
8. Williams, J. H. Acc. Chem. Res. 1993, 26, 593.
9. Hunter, C. A.; Sanders, J. K. M. J. Am. Chem. Soc. 1990, 112, 5525.
10. Schmidbauer, H. Angew. Chem., Int. Ed. Engl. 1985, 24, 893.
11. Basch, H. Inorg. Chim. Acta 1996, 242, 191.
12. Burford, N.; Clyburne, J. A. C.; Bakshi, P. K.; Cameron, T. S. Organometallics 1995, 14, 1578.
13. Kim, E. K.; Kochi, J. K. J. Am. Chem. Soc. 1991, 113, 4962.
14. Harmon, W. D.; Taube, H. J. Am. Chem. Soc. 1987, 109, 1883.
15. (a) Reed, C. A.; Fackler, N. L. P.; Kim, K.-C.; Stasko, D.; Evans, D. R.; Boyd, P. D. W.; Rickard, C. E. F. J. Am. Chem. Soc. 1999, 121, 6314.
16. (b) Rathore, R.; Hecht, J.; Kochi, J. K. J. Am. Chem. Soc. 1998, 120, 13278.
17. Reed, C. A.; Xie, Z.; Bau, R.; Benesi, A. Science 1993, 262, 402.
18. Reed, C. A. Acc. Chem. Res. 1998, 31, 325.
19. Hair, G. S.; Cowley, A. H.; Jones, R. A.; McBurnett, B. G.; Voigt, A. J. Am. Chem. Soc. 1999, 121, 4922.
20. Miklis, P. C.; Ditchfield, R.; Spencer, T. A. J. Am. Chem. Soc. 1998, 120, 10482.
21. Xie, Z.; Bau, R.; Reed, C. A. Angew. Chem., Int. Ed. Engl. 1994, 33, 2433.
22. Williamson, M. M.; Hill, C. L. Inorg. Chem. 1987, 26, 4155.
23. Reed, C. A. Acc. Chem. Res. 1998, 31, 133.
24. Evans, D. E.; Reed, C. A. Submitted for publication.
25. Reed, C. A.; Guiset, F. J. Am. Chem. Soc. 1996, 118, 3281.
26. Byrn, M. P.; Curtis, C. J.; Hsiou, Y.; Khan, S. I.; Sawin, P. A.; Tendick, S. K.; Terzis, A.; Strouse, C. E. J. Am. Chem. Soc. 1993, 115, 9480.
27. Scheidt, W. R.; Lee, Y. J. In Structure and Bonding; Springer-Verlag: Berlin, 1987; p 1.
28. Gupta, P. G.; Lang, G.; Lee, Y. J.; Scheidt, W. R.; Shelly, K.; Reed, C. A. Inorg. Chem. 1987, 26, 3022.
29. Matsuzawa, N.; Ata, M.; Dixon, D. A. J. Phys. Chem. 1995, 99, 7698.
30. Delley, B. Physica B 1991, 172, 185.
31. Obara, S.; Kashiwagi, H. J. Chem. Phys. 1982, 77, 3155.
32. Jones, D. H.; Hinman, A. S.; Ziegler, T. Inorg. Chem. 1993, 32, 2092.
33. Ghosh, A.; Almlöf, J.; Que, L. J. Phys. Chem. 1994, 98, 5576.
34. Almlöf, J.; Fischer, T. H.; Gassman, P. G.; Ghosh, A.; Häser, M. J. Phys. Chem. 1993, 97, 10964.
35. Kuramochi, H.; Noodleman, L.; Case, D. A. J. Am. Chem. Soc. 1997, 119, 11442.
36. Scheidt, W. R.; Reed, C. A. Chem. Rev. 1981, 81, 543.
37. Morokuma, K. J. Chem. Phys. 1971, 55, 1236. Ziegler, T.; Rauk, A. Theor. Chim. Acta 1977, 49, 1. Van den Hoek, P. J.; Kleyn, A. W.; Baerends, E. J. Comments At. Phys. 1989, 23, 93.
38. Morokuma, K. J. Chem. Phys. 1971, 55, 1236. Ziegler, T.; Rauk, A. Theor. Chim. Acta 1977, 49, 1. Van den Hoek, P. J.; Kleyn, A. W.; Baerends, E. J. Comments At. Phys. 1989, 23, 93.
39. Morokuma, K. J. Chem. Phys. 1971, 55, 1236. Ziegler, T.; Rauk, A. Theor. Chim. Acta 1977, 49, 1. Van den Hoek, P. J.; Kleyn, A. W.; Baerends, E. J. Comments At. Phys. 1989, 23, 93.
40. Haddon, R. C. J. Comput. Chem. 1998, 19, 139.
41. Penicaud, A.; Hsu, J.; Reed, C. A. J. Am. Chem. Soc. 1991, 113, 6698.
42. Balch, A. L.; Olmstead, M. M. Chem. Rev. 1998, 98, 2123.
43. Maruyama, H.; Fujiwara, M.; Tanaka, K. Chem. Lett. 1998, 805.
44. (a) Xiao, J.; Savina, M. R.; Martin, G. B.; Francis, A. H.; Meyerhoff, M. E. J. Am. Chem. Soc. 1994, 116, 9341.
45. (b) Xiao, J.; Meyerhoff, M. E. J. Chromatogr. 1995, 715, 19.
46. Boyd, P. D. W.; Hodgson, M. C.; Rickard, C. E. F.; Oliver, A. G.; Brothers, P. J.; Bolskar, R. D.; Reed, C. A. J. Am. Chem. Soc., in press.
47. Reed, C. A.; Mashiko, T.; Bentley, S. P.; Kastner, M. E.; Scheidt, W. R.; Spartalian, K.; Lang, G. J. Am. Chem. Soc. 1979, 101, 2948.
48. Barkigia, K. M.; Berber, M. D.; Fajer, J.; Medforth, C. J.; Renner, M.; Smith, K. M. J. Am. Chem. Soc. 1990, 112, 8851.
49. Martín, N.; Sánchez, L.; Illescas, B.; Pérez, I. Chem. Rev. 1998, 98, 2527.
50. Smirnov, V. V.; Woller, E. K.; DiMagno, S. G. Inorg. Chem. 1998, 37, 4971.
51. Kirner, J. F.; Reed, C. A.; Scheidt, W. R. J. Am. Chem. Soc. 1977, 99, 1093.
52. Kadish, K. M.; Araullo-McAdams, C.; Han, B. C.; Frazen, M. M. J. Am. Chem. Soc. 1990, 112, 8364.
53. Evans, D. R.; Drovetskaya, T.; Bau, R.; Reed, C. A.; Boyd. P. D. W. J. Am. Chem. Soc. 1997, 119, 3633.
54. For a recent example, see: Armaroli, N.; Diederich, F.; Echegoyen, L.; Habicher, T.; Flamigni, L.; Marconi, G.; Nierengarten, J.-F. New. J. Chem. 1999, 77.
55. Lambert, J. B.; Zhang, S.; Ciro, S. M. Organometallics 1994, 13, 2430.
56. (a) ADF 2.3.0, Theoretical Chemistry, Vrije Universiteit, Amsterdam.
57. (b) Baerends, E. J.; Ellis, D. E.; Ros, P. Chem. Phys. 1973, 2, 41.
58. (c) te Velde, G.; Baerends, E. J. J. Comput. Phys. 1992, 99, 84.
59. Vosko, S. H.; Wilk, L.; Nusair, M. Can. J. Phys. 1980, 58, 1200.
60. Becke, A. D. Phys. Rev. A 1988, 38, 3098.
61. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
62. Sheldrick, G. M. Bruker AXS: Madison, WI, 1997.
63. Sheldrick, G. M. SHELXS97, A Program for Crystal Structure Solution; University of Göttingen, Germany, 1997.
64. Sheldrick, G. M. SHELXL97, A Program for Crystal Structure Refinement; University of Göttingen, Germany, 1997.
65. Spek, A. L. Acta Crystallogr. 1990, A46, C34.
66. Sluis, P. V. D.; Spek, A. L. Acta Crystallogr. 1990, A46, 194.