Carbon-carbon bonds functioning as electron shuttles: The generation of electron-rich manganese(II)-schiff base complexes and their redox chemistry

Journal of the American Chemical Society

Volumn 119, Issue 22, 1997, Pages 5144-5154

  Gallo, Emma ^a   Solari, Euro ^a   Re, Nazzareno ^b   Floriani, Carlo ^a   Chiesi Villa, Angiola ^c   Rizzoli, Corrado ^c  

^a UNIVERSITY OF LAUSANNE   (Switzerland)

^b UNIVERSITY OF PERUGIA   (Italy)

^c UNIVERSITY OF PARMA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; DIMER; FREE RADICAL; MANGANESE DERIVATIVE; SCHIFF BASE;

ARTICLE; COVALENT BOND; ELECTRON TRANSPORT; OXIDATION REDUCTION REACTION;

EID: 0030878478     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9640962     Document Type: Article

References (88)

1. (a) Photosynthesis; Briggs, W. R., Ed.; ARL: New York, 1989.
2. (b) The Photosynthetic Reaction Center. Deisenhofer, J., Norris, J. R., Eds.; Academic: New York, 1993 Vol. I and II.
3. (c) Manganese Redox Enzymes; Pecoraro, V. L., Ed.; VCH: New York, 1992.
4. (d) Wieghardt, K. Angew. Chem., Int. Ed. Engl. 1989, 28, 1153.
5. (a) Foster, R. Organic Charge Transfer Complexes; Academic: London, 1969.
6. (b) Miller, L. L.; Mann, K. R. Acc. Chem. Res. 1996, 29, 417.
7. Fluharty, A. L. In The chemistry of the thiol group; Patai, Ed.; Wiley: London, 1974; Chapter 13, p 601.
8. Gambarotta, S.; Floriani, C.; Chiesi-Villa, A.; Guastini, C. J. Chem. Soc., Chem. Commun. 1982, 756.
9. (b) Gambarotta, S.; Urso, F.; Floriani, C.; Chiesi-Villa, A.; Guastini, C. Inorg. Chem. 1983, 22, 3966.
10. (c) Gambarotta, S.; Mazzanti, M.; Floriani, C.; Zehnder, M. J. Chem. Soc., Chem. Commun. 1984, 1116.
11. (d) De Angelis, S.; Solari, E.; Gallo, E.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Inorg. Chem. 1996, 35, 5995 and references therein.
12. Gallo, E.; Solari, E.; De Angelis, S.; Floriani, C.; Re, N.; Chiesi-Villa, A.; Rizzoli, C. J. Am. Chem. Soc. 1993, 115, 9850.
13. (a) Guerriero, P.; Tamburini, S.; Vigato, P. A. Coord. Chem. Rev. 1995, 139, 17.
14. (b) Floriani, C.; Calderazzo, F.; Randaccio, L. J. Chem. Soc., Chem. Commun. 1973, 384.
15. (c) Gambarotta, S.; Corazza, F.; Floriani, C.; Zehnder, M. J. Chem. Soc., Chem. Commun. 1984, 1305.
16. (d) Horwitz, C. P.; Ciringh, Y. Inorg. Chim. Acta 1994, 225, 191.
17. (e) Bresciani-Pahor, N.; Calligaris, M.; Delise, P.; Nardin, G.; Randaccio, L.; Zotti, E.; Fachinetti, G.; Floriani, C. J. Chem. Soc., Dalton Trans. 1976, 2310.
18. (f) Horwitz, C. P.; Warden, J. T.; Weintraub, S. T. Inorg. Chim. Acta 1996, 246, 311-320.
19. (g) Giacomelli, A.; Floriani, C.; Perego, G. J. Chem. Soc., Chem. Commun. 1982, 650.
20. (h) Solari, E.; Floriani, C.; Cunningham, D.; Higgins, T.; McArdle, P. J. Chem. Soc., Dalton Trans. 1991, 3139.
21. (i) Gibney, B. R.; Wang, H.; Kampf, J. W.; Pecoraro, V. L. Inorg. Chem. 1996, 35, 6184.
22. Solari, E.; Musso, F.; Gallo, E.; Floriani, C.; Re, N.; Chiesi-Villa, A.; Rizzoli, C. Organometallics 1995, 14, 2265.
23. Srinavan, K.; Michaud, J. K. J. Am. Chem. Soc. 1986, 108, 2309.
24. (a) Luaces, L.; Bermejo, M: R.; Garcia-Vazquez, J. A.; Romero, S.; Sousa, A.; Watkinson, M.; Mugnier, Y.; McAuliffe, C. A.; Pritchard, R. G.; Helliwell, M. Polyhedron 1996, 15, 1375.
25. (b) Higuchi, C.; Sakiyama, H.; Okawa, H.; Isobe, R.; Fenton, D. E. J. Chem. Soc., Dalton Trans. 1994, 1097.
26. (c) Kessissoglou, D. P.; Butler, W. M.; Pecoraro, V. L. Inorg. Chem. 1987, 26, 495.
27. (d) Mabad, B.; Cassoux, P.; Tuchagues, J.-P.; Hendrickson, D. N. Inorg. Chem. 1986, 25, 1420.
28. (e) Gallo, E.; Solari, E.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Organometallics 1995, 14, 2156.
29. O'Connor, C. J. Progr. Inorg. Chem. 1982, 29, 203.
30. A detailed report on the magnetic properties of all the dimeric compounds cited in this paper is in the Supporting Information.
31. (a) Manchanda, R.; Brudvig, G. W.; Crabtree, R. H. Coord. Chem. Rev. 1995, 144, 1.
32. (b) Pecoraro, V. L.; Baldwin, M. S.; Gelasco, A. Chem. Rev. 1994, 94, 807.
33. Weiss, E. Angew. Chem., Int. Ed. Engl. 1993, 32, 1501.
34. (a) Allinger, N. Org. Synth. 1963, IV, 840.
35. (b) Bloomfield, J. J.; Owsley, D. C.; Ainsworth, C.; Robertson, R. E. J. Org. Chem. 1975, 40, 393.
36. (c) Schreibmann, A. A. P. Tetrahedron Lett. 1970, 4271.
37. (d) Smith, J. G.; Ho, I. J. Org. Chem. 1972, 37, 653.
38. (e) Jaunin, R.; Holl, R. Helv. Chim. Acta 1958, 41, 1783.
39. (f) Jaunin, R.; Magnenat, J.-P. Helv. Chim. Acta 1959, 42, 328.
40. (g) Bastian, J.-M.; Jaunin, R. Helv. Chim. Acta 1963, 46, 1248.
41. (h) Shono, T.; Kise, N; Okazaki, E. Tetrahedron Lett. 1992, 33, 3347.
42. Wieghardt, K.; Bossek, U.; Nuber, B.; Weiss, J.; Bonvoisin, J.; Corbella, M.; Vitols S. E.; Girerd, J.-J. J. Am. Chem. Soc. 1988, 110, 7398.
43. Menage, S.; Vitols, S. E.; Bergerat, P.; Codjovi, E.; Kahn, O.; Girerd, J.-J.; Guillot, M.; Solans X.; Calvet, T. Inorg. Chem. 1991, 30, 2666.
44. Wieghart, K.; Bossek, K.; Bonvoisin, J.; Beauvillain, P.; Girerd, J.-J.; Nuber, B.; Weiss J.; Heinze, J. Angew. Chem., Int. Ed. Engl., 1986, 25, 1030.
45. Connelly, N. G.; Geiger, W. E. Chem. Rev. 1996, 96, 877.
46. Floriani, C.; Fachinetti, G. J. Chem. Soc., Chem. Commun. 1973, 17.
47. Depew, M. C.; Wan, J. K. S. in The Chemistry of Quininoid Compounds; Patai, I., Rappoport, Z., Eds; Wiley: New York, 1988; Vol. 21.
48. Fachinetti, G.; Floriani, C.; Zanazzi, P. F.; Zanzari, A. R. Inorg. Chem. 1979, 18, 3469.
49. (a) Sweany, R. L. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, U.K., 1995; Vol. 8; Chapter 1, p 42, and references therein.
50. (b) Calligaris, M.; Randaccio, L. In Comprehensive Coordination Chemistry; Wilkinson, G., Gillard, R. D., McCleverty, J. A., Eds.; Pergamon: Oxford, U.K., 1987.
51. (c) Pratt, J. M.; Craig, P. J. Adv. Organomet. Chem. 1973, 11, 404.
52. (d) Calligaris, M.; Nardin, G.; Randaccio, L. Coord. Chem. Rev. 1972, 7, 385.
53. (e) Bigotto, A.; Costa, G.; Mestroni, G.; Pellizzer, G.; Puxeddu, A.; Reisenhofer, E.; Stefani, L.; Tauzher, G. Inorg. Chim. Acta 1970, 4, 41.
54. (f) Pattenden, G. Chem. Soc. Rev. 1988, 17, 361 and references therein.
55. (g) Dodd, D.; Johnson, M. D. J. Organomet. Chem. 1973, 52, 1.
56. (h) Pratt, J. M.; Craig, P. J. Adv. Organomet. Chem. 1973, 11, 414.
57. (i) Randaccio, L.; Bresciani-Pahor, N.; Zangrando, E.; Marzilli, L. G. Chem. Soc. Rev. 1989, 18, 225.
58. (j) Charlaud, J.-P.; Zangrando, E.; Bresciani-Pahor, N.; Randaccio, L.; Marzilli, L. G. Inorg. Chem. 1993, 32, 4256.
59. (a) Coleman, W. M.; Taylor, L. T. Coord. Chem. Rev. 1980, 32, 1.
60. (b) Horwitz, C. P.; Dailey, G. C.; Comments Inorg. Chem. 1993, 14, 283.
61. (c) Bossek, U.; Weyehermüller, T.; Wieghardt, K.; Nuber, B.; Weiss, J. J. Am. Chem. Soc. 1990, 112, 6387.
62. (a) Yamada, T.; Imagawa, K.; Nagata, T.; Mukaiyama, T. Chem. Lett. 1992, 2231.
63. (b) Mukaiyama, T.; Yamada, T.; Nagata, T.; Imagawa, K. Chem. Lett. 1993, 327.
64. (c) Nagata, T.; Imagawa, K.; Yamada, T.; Mukaiyama, T. Inorg. Chim. Acta 1994, 220, 283.
65. (d) Nagata, T.; Imagawa, K.; Yamada, T.; Mukaiyama, T. Chem. Lett. 1994, 1259.
66. (e) Imagawa, K.; Nagata, T.; Yamada, T.; Mukaiyama, T. Chem. Lett. 1995, 335.
67. (f) MacDonnel, F. M.; Fackler, N. L. P.; Stern, C.; O'Halloran, T. V. J. Am. Chem. Soc. 1994, 116, 7431.
68. (g) Nagata, T.; Imagawa, K.; Yamada, T.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1995, 68, 3241.
69. (a) Brudvig, G. W.; Crabtree, R. H. Proc. Natl. Acad. Sci. U.S.A. 1986, 83, 4586.
70. (b) Brudvig, G. W.; Crabtree, R. H. Progress in Inorganic Chemistry; 1989; Vol. 37.
71. (c) Dismukes, G. C. Chem. Scr. 1988, 28A, 99.
72. Torayama, H.; Nishide, T.; Asada, H.; Fujiwara, M.; Matsushita, T. Chem. Lett. 1996, 387-388..
73. Bermejo, M. R.; Castiñeiras, A.; Garcia-Monteagudo, J. C.; Rey, M.; Sousa, A.; Watkinson, M.; McAuliffe, C. A.; Pritchard, R. G.; Beddoes, R. L. J. Chem. Soc., Dalton Trans. 1996, 2935-2944.
74. Gallo, E.; Solari, E.; Re, N.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1981-1983.
75. Libby, E.; Webb, R. J.; Streib, W. E.; Folting, K.; Huffman, J. C.; Hendrickson, D. N.; Christou, J. Inorg. Chem. 1989, 28, 4037.
76. Lorrow, J. F.; Jacobsen, E. N.; Gao, Y.; Hong, Y.; Nie, X.; Zepp, C. M. J. Org. Chem. 1994, 59, 1939.
77. Press, W. H.; Flannery, B. P.; Teukolsky, S. A.; Vetterling, W. T. Numerical Recipes; Cambridge University Press: Cambridge, U.K., 1989.
78. Lawton, S. L.; Jacobson, R. A. "TRACER", a cell reduction program; Ames Laboratory: Iowa State University of Science and Technology, 1965.
79. Lehmann, M. S.; Larsen, F. K. Acta Crystallogr. Sect. A: Cryst. Phys. Diffr. Theor. Gen. Crystallogr. 1974, A30, 580.
80. Data reduction, structure solution, and refinement were carried out on a Quansan personal computer equipped with an INTEL Pentium processor and on an Encore 91 computer.
81. Wilson, A. J. C. Nature (London) 1942, 150, 151.
82. Ugozzoli, F. Comput. Chem. 1987, 11, 109.
83. North, A. C. T.; Phillips, D. C.; Mathews, F. S. Acta Crystallogr., Sect. A: Cryst. Phys., Diffr., Theor. Gen. Crystallogr. 1968, A24, 351-359.
84. International Tables for X-ray Crystallography; Kynoch Press: Birmingham, England, 1974; Vol. IV, (a) p 99, (b) p 149.
85. Stewart, R. F.; Davidson, E. R.; Simpson, W. T. J. Chem. Phys. 1965, 42, 3175.
86. Sheldrick, G. M. SHELX76, Program for crystal structure determination, University of Cambridge: Cambridge, England, 1976.
87. Sheldrick, G. M. SHELXL92, Program for crystal structure refinement; University of Göttingen, Göttingen, Germany, 1992.
88. See the paragraph at the end of the paper regarding the Supporting Information.