Investigations of time-dependent delocalization and the correlation of carbonyl IR shifts with ΔE(1/2) values for hydrocarbon-linked class II and class III mixed-valent complexes

Journal of the American Chemical Society

Volumn 122, Issue 23, 2000, Pages 5477-5485

  Atwood, Christopher G ^a   Geiger, William E ^a  

^a UNIVERSITY OF VERMONT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL DERIVATIVE; HYDROCARBON; MANGANESE DERIVATIVE; METAL COMPLEX; NITROGEN;

ARTICLE; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; ELECTROCHEMICAL ANALYSIS; ELECTROCHEMISTRY; ELECTRON SPIN RESONANCE; ELECTRON TRANSPORT; ENERGY TRANSFER; INFRARED SPECTROMETRY; OXIDATION REDUCTION REACTION; REACTION ANALYSIS;

EID: 0034647229     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja994064p     Document Type: Article

References (112)

1. (a) Müller, A., Ed. Electron and Proton Transfer in Chemistry and Biology; Elsevier: Amsterdam, 1990.
2. (b) Marcus, R. A.; Sutin, N. Biochim. Biophys. Acta 1985, 811, 265.
3. (c) Stachlin, L. A.; Arntzen, C. J., Eds. Photosynthesis; Springer-Verlag: New York, 1986.
4. (d) Dismukes, G. C. Chem. Rev. 1996, 96, 2909.
5. (e) Mouesca, J.-M.; Lamotte, B. Coord. Chem. Rev. 1998, 178, 1573.
6. (a) The following contains leading references: Zhu, S. S.; Swager, T. M. J. Am. Chem. Soc. 1997, 119, 12568.
7. See also: (b) Cayton, R. H.; Chisholm, M. H. J. Am. Chem. Soc. 1989, 111, 8921.
8. Reviewed in: (a) Boulas, P. L.; Gomez-Kaifer, M.; Echegoyen, L. Angew. Chem., Int. Ed. Engl. 1998, 37, 217. (b) De Cola, L.; Belser, P. Coord. Chem. Rev. 1998, 177, 301.
9. Reviewed in: (a) Boulas, P. L.; Gomez-Kaifer, M.; Echegoyen, L. Angew. Chem., Int. Ed. Engl. 1998, 37, 217. (b) De Cola, L.; Belser, P. Coord. Chem. Rev. 1998, 177, 301.
10. Astruc, D. Electron-Transfer Processes in Transition Metal Chemistry; VCH Publishers: New York, 1995.
11. Leading references may be found in ref 4 and in the following: (a) Chin, T. T.; Grimes, R. N.; Geiger, W. E. Inorg. Chem. 1999, 38, 93. (b) Dong, T.-Y.; Lee, S.-H.; Chang, C.-K.; Lin, H.-M.; Lin, K.-J. Organometallics 1997, 16, 2773. (c) Hendrickson, D. N.; Oh, S. M.; Dong, T.-Y.; Moore, M. F. Comments Inorg. Chem. 1985, 4, 329.
12. Leading references may be found in ref 4 and in the following: (a) Chin, T. T.; Grimes, R. N.; Geiger, W. E. Inorg. Chem. 1999, 38, 93. (b) Dong, T.-Y.; Lee, S.-H.; Chang, C.-K.; Lin, H.-M.; Lin, K.-J. Organometallics 1997, 16, 2773. (c) Hendrickson, D. N.; Oh, S. M.; Dong, T.-Y.; Moore, M. F. Comments Inorg. Chem. 1985, 4, 329.
13. Leading references may be found in ref 4 and in the following: (a) Chin, T. T.; Grimes, R. N.; Geiger, W. E. Inorg. Chem. 1999, 38, 93. (b) Dong, T.-Y.; Lee, S.-H.; Chang, C.-K.; Lin, H.-M.; Lin, K.-J. Organometallics 1997, 16, 2773. (c) Hendrickson, D. N.; Oh, S. M.; Dong, T.-Y.; Moore, M. F. Comments Inorg. Chem. 1985, 4, 329.
14. (a) Dong, T.-Y.; Lee, S.-H.; Lee, T.-Y. Organometallics 1996, 15, 2354.
15. (b) Dong, T.-Y.; Huang, C.-H.; Chang, C.-K.; Hsieh, H.-C.; Peng, S.-M.; Lee, G.-N. Organometallics 1995, 14, 1776.
16. (c) Jang, H. G.; Wittebort, R. J.; Sorai, M.; Kaneko, Y.; Nakano, M.; Hendrickson, D. N. Inorg. Chem. 1995, 31, 2265.
17. (d) Webb, R. J.; Dong, T.-Y.; Pierpont, C. C.; Boone, S. R.; Chadha, R. K.; Hendrickson, D. N. J. Am. Chem. Soc. 1991, 113, 4806.
18. (e) Dong, T.-Y.; Hsu, T.-L. J. Organomet. Chem. 1989, 367, 313.
19. (f) Dong, T.-Y.; Hendrickson, D. N.; Iwai, K.; Cohn, M. J.; Geib, S. J.; Rheingold, A. L.; Sano, H.; Motoyama, L.; Nakashima, S. J. Am. Chem. Soc. 1985, 107, 7986.
20. (g) Hupp, J. T.; Dong, Y. J. Am. Chem. Soc. 1993, 115, 6428.
21. (h) Sinha, U.; Lowrey, M. D.; Hammack, W. S.; Hendrickson, D. N.; Drickamer, H. G. J. Am. Chem. Soc. 1987, 109, 7340.
22. (a) Chen, P.; Meyer, T. J. Chem. Rev. 1998, 98, 1439.
23. (b) Neyhart, G. A.; Hupp, J. T.; Curtis, J. C.; Timpson, C. J.; Meyer, T. J. J. Am. Chem. Soc. 1996, 118, 3724.
24. (c) Sullivan, E. P., Jr.; Hazzard, J. T.; Tollin, G.; Enemark, J. H. J. Am. Chem. Soc. 1992, 114, 9662.
25. (d) Todd, M. D.; Dong, Y.; Hupp, J. T. Inorg. Chem. 1991, 30, 4685.
26. (e) Lewis, N. A.; Obeng, Y. S. J. Am. Chem. Soc. 1988, 110, 2306.
27. (f) Delville, M-H.; Lacoste, M.; Astruc, D. J. Am. Chem. Soc. 1992, 114, 8310.
28. (a) Brady, M.; Weng, W.; Zhou, Y.; Seyler, J. W.; Amorso, A. J.; Arif, A. M.; Böhme, M.; Frenking, G.; Gladysz, J. A. J. Am. Chem. Soc. 1997, 119, 775.
29. (b) Alias, Y.; Abasq, M.-L.; Barriere, F.; Davies, S. C.; Fairhurst, S. A.; Hughes, D. L.; Ibrahim, S. K.; Talarmin, J.; Pickett, C. J. Chem. Soc., Chem. Commun. 1998, 675.
30. (c) Tolbert, L. M.; Zhao, X.; Ding, Y.; Bottomley, L. A. J. Am. Chem. Soc. 1995, 117, 12891.
31. (d) Sponsler, M. D. Organometallics 1995, 14, 1920.
32. (e) Watanabe, M.; Iwamoto, T. I.; Nakashima, S.; Sakai, H.; Motoyama, I.; Sano, H. J. Organomet. Chem. 1993, 448, 167.
33. (f) Dong, T.-Y.; Hwang, M.-Y.; Wen, Y.-S.; Hwang, W.-S. J. Organomet. Chem. 1990, 391, 377.
34. (g) Ratner, M. A. J. Phys. Chem. 1990, 94, 4877.
35. (a) Creutz, C. Prog. Inorg. Chem. 1983, 30, 1.
36. (b) Crutchley, R. J. Adv. Inorg. Chem. 1994, 33, 273.
37. (c) Paul, F.; Lapinte, C. Coord. Chem. Rev. 1998, 175, 431.
38. Atwood, C. G.; Geiger, W. E.; Rheingold, A. L. J. Am. Chem. Soc. 1993, 115, 5310.
39. Abbreviations in this paper: CV = cyclic voltammetry; Dcm = dicyclopentadienyl methane; dppm = bis(diphenylphosphino)methane; Fluor = fluorene; Fulv = fulvalenediyl; Phen = 9,10-dihydrophenanthrene; SSV = steady-state voltammetry.
40. (a) Robin, M. B.; Day, P. Adv. Inorg. Chem. Radiochem. 1967, 10, 247.
41. (b) Cannon, R. D. Electron-Transfer Reactions; Butterworths: London, 1980; p 286ff.
42. Creutz, C.; Taube, H. J. Am. Chem. Soc. 1969, 91, 3988. Creutz, C.; Taube, H. J. Am. Chem. Soc. 1973, 95, 1086.
43. Creutz, C.; Taube, H. J. Am. Chem. Soc. 1969, 91, 3988. Creutz, C.; Taube, H. J. Am. Chem. Soc. 1973, 95, 1086.
44. (a) Zhang, L.-T.; Ko, J.; Ondrechen, M. J. J. Am. Chem. Soc. 1987, 109, 1666.
45. (b) Ondrechen, M. J.; Ko, J.; Zhang, L.-T. J. Am. Chem. Soc. 1987, 109, 1672.
46. For leading references see: (a) Fürholz, U.; Bürgi, H.-B.; Wagner, F. E.; Stabler, A.; Ammeter, J. H.; Krausz, E.; Clark, R. J. H.; Stead, M. J.; Ludi, A. J. Am. Chem. Soc. 1984, 106, 121. (b) Best, S. P.; Clark, R. J. H.; McQueen, R. S. C.; Joss, S. J. Am. Chem. Soc. 1989, 111, 548.
47. For leading references see: (a) Fürholz, U.; Bürgi, H.-B.; Wagner, F. E.; Stabler, A.; Ammeter, J. H.; Krausz, E.; Clark, R. J. H.; Stead, M. J.; Ludi, A. J. Am. Chem. Soc. 1984, 106, 121. (b) Best, S. P.; Clark, R. J. H.; McQueen, R. S. C.; Joss, S. J. Am. Chem. Soc. 1989, 111, 548.
48. (a) Ito, T.; Hamaguchi, T.; Nagino, H.; Yamaguchi, T.; Washington, J.; Kubiak, C. Science 1997, 277, 660.
49. (b) Ito, T.; Hamaguchi, T.; Nagino, H.; Yamaguchi, T.; Kido, H.; Zavarine, I. S.; Richmond, T.; Washington, J.; Kubiak, C. J. Am. Chem. Soc. 1999, 121, 4625.
50. (a) McManis, G. E.; Nielson, R. M.; Weaver, M. J. Inorg. Chem. 1988, 27, 1827.
51. (b) Manriquez, J. M.; Ward, M. D.; Reiff, W. M.; Calabrese, J. C.; Jones, N. L.; Carroll, P. J.; Bunel, E. E.; Miller, J. S. J. Am. Chem. Soc. 1995, 117, 6182.
52. (c) Lambert, C.; Noell, G. J. Am, Chem. Soc. 1999, 121, 8384.
53. Jones, P. L.; Jeffrey, J. C.; Maher, J. P.; McCleverty, J. A.; Rieger, P. H.; Ward, M. D. Inorg. Chem. 1997, 36, 3088.
54. Evans, C. E. B.; Naklicki, M. L.; Rezvani, A. R.; White, C. A.; Kondratiev, V. V.; Crutchley, R. J. J. Am. Chem. Soc. 1998, 120, 13096.
55. Rocha, R. C.; Araki, K.; Toma, H. E. Inorg. Chim. Acta 1999, 285, 197.
56. (a) Demadis, K. D.; El-Samonody, E. S.; Coia, G. M.; Meyer, T. J. J. Am. Chem. Soc. 1999, 121, 535.
57. (b) Neyhart, G. A.; Timpson, C. J.; Bates, W. D.; Meyer, T. J. J. Am. Chem. Soc. 1996, 118, 3730.
58. Stoll, M. E.; Lovelace, S. R.; Geiger, W. E.; Schimanke, H.; Hyla-Kryspin, I.; Gleiter, R. J. Am. Chem. Soc. 1999, 121, 9343.
59. 1/2 values: Ward, M. D. Chem. Soc. Rev. 1995, 121.
60. (a) Allen, G. C.; Hush, N. S. Prog. Inorg. Chem. 1967, 8, 357.
61. (b) Hush, N. S. Prog. Inorg. Chem. 1967, 8, 391.
62. (a) Nakamoto, K. Infrared and Roman Spectra of Inorganic and Coordination Compounds, 4th ed.; John Wiley: New York, 1986; pp 291-295.
63. (b) Willner, H.; Aubke, F. Angew. Chem., Int. Ed. 1997, 36, 2403.
64. (c) Goldman, A. S.; Krogh-Jespersen, K. J. Am. Chem. Soc. 1996, 118, 12159.
65. -13 s are commonly quoted for IR spectroscopy. See ref 16b for a discussion and leading references.
66. Moore, M. F.; Hendrickson, D. N. Inorg. Chem. 1985, 24, 1236.
67. Bignozzi, C. A.; Argazzi, R.; Schoonover, J. R.; Gordon, K. C.; Dyer, R. B.; Scandola, F. Inorg. Chem. 1992, 31, 5260.
68. (a) Delville, M.-H.; Rittinger, S.; Astruc, D. A. J. Chem. Soc., Chem. Commun. 1992, 519.
69. (b) Ketterle, M.; Fiedler, J.; Kaim, W. J. Chem. Soc., Chem. Commun. 1998, 1701.
70. George, M. W.; Turner, J. J. Coord. Chem. Rev. 1998, 177, 201.
71. For an organic example involving quinone redox sites see: Almlöf, J. E.; Feyereisen, M. W.; Jozefiak, T. H.; Miller, L. L. J. Am. Chem. Soc. 1994, 112, 1206.
72. Atwood, C. G.; Geiger, W. E.; Bitterwolf, T. E. J. Electroanal. Chem. 1995, 397, 279.
73. 6, M = Cr, Mo, W. See:(a) Moulton, R.; Weidman, T. W.; Vollhardt, K. P. C.; Bard, A. J. Inorg. Chem. 1986, 25, 1846. (b) Kovacs, I.; Baird, M. C. Organometallics 1996, 15, 3588. (c) Brown, D.; Delville, M.-H.; Volhardt, K. P. C.; Astruc, D. New J. Chem. 1992, 16, 899.
74. 6, M = Cr, Mo, W. See:(a) Moulton, R.; Weidman, T. W.; Vollhardt, K. P. C.; Bard, A. J. Inorg. Chem. 1986, 25, 1846. (b) Kovacs, I.; Baird, M. C. Organometallics 1996, 15, 3588. (c) Brown, D.; Delville, M.-H.; Volhardt, K. P. C.; Astruc, D. New J. Chem. 1992, 16, 899.
75. 6, M = Cr, Mo, W. See:(a) Moulton, R.; Weidman, T. W.; Vollhardt, K. P. C.; Bard, A. J. Inorg. Chem. 1986, 25, 1846. (b) Kovacs, I.; Baird, M. C. Organometallics 1996, 15, 3588. (c) Brown, D.; Delville, M.-H.; Volhardt, K. P. C.; Astruc, D. New J. Chem. 1992, 16, 899.
76. (a) Morrison, W. H., Jr.; Hendrickson, D. N. Inorg. Chem. 1975, 14, 2331.
77. (b) Le Vanda, C.; Bechgaard, K.; Cowan, D. O.; Mueller-Westerhoff, U. T.; Eilbracht, P.; Candela, G. A.; Collins, R. L. J. Am. Chem. Soc. 1976, 98, 3181.
78. (c) Böhm, M. C.; Gleiter, R.; Delgado-Pena, F.; Cowan, D. O. J. Chem. Phys. 1983, 79, 1154.
79. (d) Kirchner, R. F.; Loew, G. H.; Mueller-Westerhoff, U. T. Inorg. Chem. 1976, 15, 2665.
80. (a) Clark, S. F.; Watts, R. J.; Dubois, D. L.; Connolly, J. S.; Smart, J. C. Coord. Chem. Rev. 1985, 64, 273.
81. (b) Davison, A.; Smart, J. C. J. Organomet. Chem. 1973, 49, C43.
82. (c) Kramer, J. A.; Hendrickson, D. N. Inorg. Chem. 1980, 19, 3330.
83. Van Order, N., Jr.; Geiger, W. E.; Bitterwolf, T. E.; Rheingold, A. L. J. Am. Chem. Soc. 1987, 109, 5680.
84. Morrison, W. H., Jr.; Krogsrud, S.; Hendrickson, D. N. Inorg. Chem. 1973, 12, 1998.
85. Colbran, S. B.; Robinson, B. H.; Simpson, J. Organometallics 1984, 3, 1344.
86. Lee, M.-T.; Foxman, B. M.; Rosenblum, M. Organometallics 1985, 4, 539.
87. Bligh, R. Q.; Moulton, R.; Bard, A. J.; Piorko, A.; Sutherland, R. G. Inorg. Chem. 1989, 28, 2652.
88. Bruns, W.; Kaim, W. J. Organomet. Chem. 1990, 390, C45.
89. Siemeling, U.; Jutzi, P.; Bill, E.; Trautwein, A. X. J. Organomet. Chem. 1993, 463, 151.
90. Das, A.; Maher, J. P.; McCleverty, J. A.; Navas Badioga, J. A.; Ward, M. D. J. Chem. Soc., Dalton Trans. 1993, 681.
91. Gilbert, A. M.; Katz, T. J.; Geiger, W. E.; Robben, M. P.; Rheingold, A. L. J. Am. Chem. Soc. 1993, 115, 3199.
92. Tolbert, L. M.; Zhao, X.; Ding, Y.; Bottomley, L. A. J. Am. Chem. Soc. 1995, 117, 12891.
93. 1) at 298 K, where potentials are in units of volt.
94. There are exceptions to this rule, some of which have been noted in ref 5a. For a very recent example see: Unseld, D.; Krivykh, V. V.; Heinze, K.; Wild, F.; Artus, G.; Schmalle, H.; Berke, H. Organometallics 1999, 18, 1525.
95. (a) Manuel, T. A. Adv. Organomet. Chem. 1965, 3, 181.
96. (b) Stroheimer, V. W.; Barbeau, C. Z. Naturforsch. 1962, 17B, 848.
97. Bitterwolf, T. E. J. Organomet. Chem. 1986, 312, 197.
98. Herrmann, W. A.; Andrejewski, D.; Herdtweck, E. J. Organomet. Chem. 1980, 319, 183.
99. Pierce, D. T.; Geiger, W. E. Inorg. Chem. 1994, 33, 373.
100. Bitterwolf, T. E. J. Organomet. Chem. 1980, 252, 305.
101. -1.
102. Bullock, J. P.; Boyd, D. C.; Mann, K. R. Inorg. Chem. 1987, 26, 3084. Original cell design in: Heineman, W. R.; Burnett, J. N.; Murray, R. W. Anal. Chem. 1968, 40, 1974.
103. Bullock, J. P.; Boyd, D. C.; Mann, K. R. Inorg. Chem. 1987, 26, 3084. Original cell design in: Heineman, W. R.; Burnett, J. N.; Murray, R. W. Anal. Chem. 1968, 40, 1974.
104. Pike, R. D.; Rieger, A. L.; Rieger, P. H. J. Chem. Soc., Faraday Trans. 1989, 85, 391.
105. Overlap of central components in mixed-valent complexes having multiple carbonyls on each metal is common: see refs 32, 36, 51, and the following: (a) Geiger, W. E.; Van Order, Jr.; Pierce, D. T.; Bitterwolf, T. E.; Rheingold, A. L.; Chasteen, N. D. Organometallics 1991, 10, 2403. (b) Merkert, J. W.; Geiger, W. E.; Paddon-Row: M. N.; Oliver, A. M.; Rheingold, A. L. Organometallics 1992, 11, 4109.
106. Overlap of central components in mixed-valent complexes having multiple carbonyls on each metal is common: see refs 32, 36, 51, and the following: (a) Geiger, W. E.; Van Order, Jr.; Pierce, D. T.; Bitterwolf, T. E.; Rheingold, A. L.; Chasteen, N. D. Organometallics 1991, 10, 2403. (b) Merkert, J. W.; Geiger, W. E.; Paddon-Row: M. N.; Oliver, A. M.; Rheingold, A. L. Organometallics 1992, 11, 4109.
107. Bullock, J. P.; Mann, K. R. Inorg. Chem. 1989, 28, 4006.
108. -1). and physical state (Nujol mulls).
109. Connelly, N. G.; Geiger, W. E. Chem. Rev. 1996, 96, 877.
110. Atwood, C. G.; Geiger, W. E. J. Am. Chem. Soc. 1994, 116, 10849.
111. Ammar, F.; Saveant, J. M. J. Electroanal. Chem. 1973, 47, 215.
112. Caspar, J. V.; Westmoreland, T. D.; Allen, G. H.; Bradley, P. G.; Meyer, T. J.; Woodruff, W. H. J. Am. Chem. Soc. 1984, 106, 3492. We thank a reviewer for bringing this article to our attention.