Charge-transfer Interactions and Electron-transfer-activated Reactions of Organometallic Complexes

Electron Transfer in Chemistry

Volumn 2, Issue , 2008, Pages 618-676

  Hubig, Stephan M ^a   Kochi, Jay K ^a  

^a University of Houston   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOMETALLICS;

CHARGE TRANSFER INTERACTION; ELECTRON TRANSFER; ORGANO-METALLIC COMPLEXES;

CHARGE TRANSFER;

EID: 84948694610     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527618248.ch25     Document Type: Chapter

References (200)

1. J. K. Kochi, Organometallic Mechanisms and Catalysis, Academic Press, New York, 1978.
2. D. Astruc. Electron Transfer and Radical Processes in Transition-Metal Chemistry, VCH, New York, 1995.
3. T. M. Bockman, J. K. Kochi in Photosensitization and Photocatalysis Using Inorganic and Organometallic Compounds (Eds.: K. Kalyanasundaram, M. Grätzel), Kluwer Academic, Amsterdam, 1993, p. 407.
4. K. H. Dötz, R. W. Hoffmann (Eds.), Organic Synthesis via Organometallics, Vieweg, Braunschweig, 1991.
5. J. K. Kochi, Adv. Phys. Org. Chem. 1994, 29, 185.
6. N. G. Connelly, W. E. Geiger, Chem. Rev. 1996, 96, 877.
7. R. A. Marcus, J. Chem. Phys. 1956, 24, 966.
8. R. A. Marcus, Angew. Chem. Int. Ed. Engl. 1993, 32, 1111, and references therein.
9. N. Sutin, Acc. Chem. Res. 1968, 1, 225.
10. J. F. Endicott, K. Kumar, T. Ramasami, F. P. Rotzinger, Prog. Inorg. Chem. 1983, 30, 141, and references therein.
11. U.K. Wynne, C. Galli, R. M. Hochstrasser, J. Chem. Phys. 1994, 100, 4797.
12. T. Asahi, N. Mataga, J. Phys. Chem. 1989, 93, 6575.
13. T. Hannappel, B. Burfeindt, W. Storck, F. Willig, J. Phys. Chem. 1997, B101, 6799.
14. R. S. Mulliken, J. Am. Chem. Soc. 1950, 72, 600.
15. R. S. Mulliken, J. Am. Chem. Soc. 1952, 74, 811.
16. R. S. Mulliken, W. M. Person, Molecular Complexes, Wiley, New York, 1969.
17. J. K. Kochi in [4], p. 95.
18. Charge-transfer excitation of an electron donor-acceptor complex effects the transfer of an electron from the donor to the acceptor in less than 500 fs [11, 12].
19. G. J. Kavarnos, N. J. Turro, Chem. Rev. 1986, 86, 401.
20. R. Rathore, S. M. Hubig, J. K. Kochi, J Am. Chem. Soc. 1997, 119, 11468.
21. Note that the ion-radical pairs may have different degrees of solvation depending on the electron-transfer pathway in Scheme 1. Thus, they may exist as contact ion pairs, solvent-separated ion pairs, or fully solvated ion radicals.
22. S. Ojima, H. Miyasaka, N. Mataga, J. Phys. Chem. 1990, 94, 7534.
23. K. Kikuchi, Y, Takahashi, K. Koike, K. Wakamatsu, H. Ikeda, T. Miyashi, Z. Phys. Chem. N. F. 1990, 167, 27.
24. I. R. Gould, S. Farid, Acc. Chem. Res. 1996, 29, 522.
25. D. C. Mauzerall in Photoinduced Electron Transfer, Part A (Eds.: M. A. Fox, M. Chanon), Elsevier, New York, 1988, p. 228.
26. H. Taube, Electron-Transfer Reactions of Complex Ions in Solution, Academic, New York, 1970.
27. R. D. Cannon, Electron-Transfer Reactions, Butterworth, London, 1980.
28. L. Eberson, Adv. Phys. Org. Chem. 1982, 18, 79.
29. J. K. Kochi, Angew. Chem. Int. Ed. Engl. 1988, 27, 1227.
30. H. Zipse, Angew. Chem. Int. Ed. Engl. 1997, 36, 1697.
31. S. M. Hubig, R. Rathore, J. K. Kochi, J. Am. Chem. Soc. 1999, 121, 617.
32. S. Fukuzumi, C. L. Wong, J. K. Kochi, J. Am. Chem. Soc. 1980, 102, 2928.
33. S. Fukuzumi, K. Mochida, J. K. Kochi, J. Am. Chem. Soc. 1979, 101, 5961.
34. The ionization potential of naphthalene is IP = 8.12 [35].
35. R. C. Weast (Ed.), CRC Handbook of Chemistry and Physics, CRC Press, Boca Raton, FL, 1989, p. E-87, and references therein.
36. Ionization potentials of polyalkylbenzenes lie between 7.8 and 8.8 [35].
37. H. C. Gardner, J. K. Kochi, J. Am. Chem. Soc. 1975, 97, 1855.
38. S. Fukuzumi, J. K. Kochi, Bull. Chem. Soc. Jpn. 1983, 56, 969.
39. V. F. Traven, R. West, J. Gen. Chem. USSR 1974, 44, 1803.
40. R. J. Klingler, J. K. Kochi, J. Am. Chem. Soc. 1981, 103, 5839.
41. G. Bieri, F. Burger, E. Heilbronner, J. P. Maier, Helv. Chim. Acta 1977, 60, 2213.
42. D. K. Creber, G. M. Bancroft, Inorg. Chem. 1980, 19, 643.
43. S. Evans, J. C. Green, P. J. Joachim, A. F. Orchard, D. W. Turner, J. P. Maier, J. Chem. Soc, Faraday Trans. 2 1972, 68, 905.
44. T. A. Albright, J. K. Burdett, M.-H. Whangbo, Orbital Interactions in Chemistry, Wiley, New York, 1985, p. 393.
45. J. W. Rabalais, L. O. Werme, T. Bergmark, L. Karlsson, M. Hussain, K. Siegbahn, J. Chem. Phys. 1972, 57, 1185.
46. A. M. Stolzenberg, M. T. Stershic, J. Am. Chem. Soc 1988, 110, 6391.
47. N. Ito, T. Saji, K. Suga, S. Aoyagui, J. Organomet. Chem. 1982, 229, 43.
48. L. P. Yureva, L. N. Peregudova, L. N. Nekrasov, A. P. Korotkov, N. N. Zaitseva, N. V. Zakarin, A. Yu. Vasilkov, J. Organomet. Chem. 1981, 219, 43.
49. J. O. Howell, J. M. Goncalvez, C. Amatore, L. Klasinc, R. M. Wightman, J. K. Kochi, J. Am. Chem. Soc. 1984, 106, 3968.
50. M. K. Lloyd, J. A. McCleverty, J. A. Connor, E. M. Jones, J. Chem. Soc, Dalton Trans. 1973, 1768.
51. C. J. Pickett, D. Pletcher, J. Chem. Soc, Dalton Trans. 1976, 636.
52. B. R. Higginson, D. R. Lloyd, P. Burroughs, D. M. Gibson, A. F. Orchard, J. Chem. Soc, Faraday Trans. 2 1973, 69, 1659.
53. D. R. Lloyd, E.W. Schlag, Inorg. Chem. 1969, 8, 2544.
54. J. C. Green, S. E. Jackson, B. Higginson, J. Chem. Soc, Dalton Trans. 1975, 403.
55. J. J. Ko, T. M. Bockman, J. K. Kochi, Organometallics 1990, 9, 1833.
56. R. J. Klingler, C J. Huffman, J. K. Kochi, J. Am. Chem. Soc. 1980, 102, 208.
57. T. P. Fehlner, J. K. Kochi, unpublished results.
58. B. R. Higginson, D. R. Lloyd, S. Evans, A. F. Orchard, J. Chem. Soc., Faraday Trans. 2 1975, 71, 1913.
59. S. Cradock, E. A. V. Ebsworth, A. Robertson, J. Chem. Soc, Dalton Trans. 1973, 23.
60. R. J. Klingler, K. Mochida, J. K. Kochi, J. Am. Chem. Soc. 1979, 101, 6626.
61. D. Zhu, S. V. Lindeman, J. K. Kochi, Organometallics 1999, 18, 2241.
62. D. Zhu, J. K. Kochi, Organometallics 1999, 18, 161.
63. L. L. Miller, G. D. Nordblom, E. A. Mayeda, J. Org. Chem. 1972, 37, 916.
64. S. Murphy, G. B. Schuster, J. Phys. Chem. 1995, 99, 511.
65. A. M. Bond, R. Colton, Inorg. Chem. 1976, 15, 2036.
66. D. J. Kuchynka, J. K. Kochi, Inorg. Chem. 1989, 28, 855.
67. T. Madach, H. Vahrenkamp, Z. Naturforsch. 1979, 34b, 573.
68. C. S. Ilenda, N. E. Schore, R. G. Bergman, J. Am. Chem. Soc. 1976, 98, 255.
69. D. Miholova, A. A. Vlcek, Inorg. Chim. Acta 1980, 41, 119.
70. S. F. Clark, R. J. Watts, D. L. Dubois, J. S. Connolly, J. C. Smart, Coord. Chem. Rev. 1985, 64, 273.
71. J. A. McCleverty, Prog. Inorg. Chem. 1968, 10, 49.
72. D. B. Morse, D. N. Hendrickson, T. B. Rauchfuss, S. R. Wilson, Organometallics 1988, 7, 496.
73. P. G. Gassman, C. H. Winter, J. Am. Chem. Soc. 1986, 108, 4228.
74. C. L. Wong, J. K. Kochi, J. Am. Chem. Soc. 1979, 101, 5593.
75. K. L. Rollick, J. K. Kochi, J. Am. Chem. Soc. 1982, 104, 1319.
76. W. E. Geiger, Jr, D. E. Smith, J. Electroanal. Chem. Interfac. Electrochem. 1974, 50, 31.
77. Y. Mugnier, C. Moise, J. Tirouflet, E. Laviron, J. Organomet. Chem. 1980, 186, C49.
78. Z. J. Karpinski, J. K. Kochi, J. Organomet. Chem. 1992, 437, 211.
79. D. Astruc, Top. Curr. Chem. 1991, 160, 49.
80. U. Koelle, B. Fuss, M. V. Rajasekharan, B. L. Ramakrisna, J. H. Ammeter, M. C. Böhm, J. Am. Chem. Soc. 1984, 106, 4152.
81. R. E. Lehmann, T. M. Bockman, J. K. Kochi, J. Am. Chem. Soc. 1990, 112, 458.
82. L. J. Andrews, R. M. Keefer, Molecular Complexes in Organic Chemistry, Holden-Day, San Francisco, 1964.
83. R. Foster, Organic Charge-Transfer Complexes, Academic, New York, 1969.
84. G. Briegleb, Elektronen-Donator-Acceptor Komplexe, Springer, Heidelberg, 1961.
85. V. M. Nekipelov, K. I. Zamaraev, Coord. Chem. Rev. 1985, 61, 185.
86. M. T. Beck, Coord. Chem. Rev. 1968, 3, 91.
87. V. Balzani, N. Sabbatini, F. Scandola, Chem. Rev. 1986, 86, 319.
88. J. A. A. Ketelaar, J. Phys. Radium 1954, 15, 197.
89. M. Tamres, M. Brandon, J. Am. Chem. Soc. 1960, 82, 2134.
90. P. Debye, Z. Physik 1920, 21, 178.
91. W. J. Duffin, Electricity and Magnetism, McGraw Hill, New York, 1973, p. 79.
92. F. London, Trans. Faraday Soc. 1937, 33, 8.
93. J. P. Fackler, T. S. Davis, I. D. Chawla, Inorg. Chem. 1965, 4, 130.
94. N. Mataga, T. Kubota, Molecular Interactions and Electronic Spectra, Dekker, New York, 1970, p. 219.
95. M. Tamres, R. L. Strong in Molecular Association Vol. 2 (Ed.: R. Foster), Academic, London, 1979, p. 331.
96. D. F. Evans, J. Chem. Soc. 1953, 345.
97. H. A. Benesi, J. H. Hildebrand, J. Am. Chem. Soc. 1949, 71, 2703.
98. The term 'charge resonance' is adopted from studies with mixed-valence metal complexes and cation-radical-neutral π-dimers (D+, D ↔ D, D+) [150].
99. C. W. Davis, Ion Association, Butterworth, London, 1962.
100. M. Szwarc (Ed.), Ions and Ion Pairs in Organic Reactions, Vols. 1 and 2, Wiley, New York, 1972, 1974.
101. A. Vogler, H. Kunkely, Top. Curr. Chem. 1990, 158, 1.
102. K. I. Zamaraev, A. N. Kitaigorodskii, Coord. Chem. 1980, 6, 563.
103. O. V. Nesterov, V. M. Nekipelov, Yu. N. Chirkov, A. N. Kitaigorodskii, S. G. Entelis, Kinet. Katal. 1980, 21, 1238.
104. J. C. D. Brand, W. Snedden, Trans. Faraday Soc. 1957, 53, 894.
105. F. K. Velichko, L. V. Balabanova, T. T. Vasileva, O. P. Bondarenko, G. A. Shvekhgeimer, Isv. Akad. Nauk. SSSR, Ser. Khim. 1988, 711.
106. H. Kobayashi, M. Kobayashi, Y. Kaizu, Bull. Chem. Soc. Jpn. 1973, 46, 3109.
107. S. Fukuzumi, J. K. Kochi, J. Am. Chem. Soc. 1980, 102, 2141.
108. R. D. Schmitt, R. M. Wing, A. H. Maki, J. Am. Chem. Soc. 1969, 91, 4394.
109. W. Lau, J. K. Kochi, J. Am. Chem. Soc. 1986, 108, 6720.
110. J. M. Wallis, J. K. Kochi, J. Org. Chem. 1988, 53, 1679.
111. K. Brüggermann, J. K. Kochi, J. Org. Chem. 1992, 57, 2956.
112. K. Brüggermann, R. S. Czernuszewicz, J. K. Kochi, J. Phys. Chem. 1992, 96, 4405.
113. R. S. Drago, N. J. Rose, J. Am. Chem. Soc. 1959, 81, 6138)
114. H. C. Wang, G. Levin, M. Szwarc, J. Am. Chem. Soc. 1978, 100, 6137.
115. T. M. Bockman, J. K. Kochi, J. Am. Chem. Soc. 1989, 111, 4669.
116. M. Darensbourg, H. Barros, C. Bormann, J. Am. Chem. Soc. 1977, 99, 1647.
117. J. K. Kochi, C. H. Wei, J. Organomet. Chem. 1993, 451, 111.
118. H. C. Gardner, J. K. Kochi, J. Am. Chem. Soc. 1976, 98, 2460.
119. R. E. Lehmann, J. K. Kochi, J. Am. Chem. Soc. 1991, 113, 501.
120. R. Billing, D. Rehorek, H. Hennig, Top. Curr. Chem. 1990, 58, 166.
121. T. M. Bockman, J. K. Kochi, J. Phys. Org. Chem. 1997, 10, 542.
122. T. M. Bockman, J. K. Kochi, New J. Chem. 1992, 16, 39.
123. C. Reichardt, Solvents and Solvent Effects in Organic Chemistry, VCH, 2nd ed., Weinheim, 1988.
124. R. A. Marcus, J. Phys. Chem. 1989, 93, 3078.
125. S. M. Hubig, J. K. Kochi. J. Phys. Chem. 1995, 99, 17578.
126. C. Reichardt, Chem. Soc. Rev. 1992, 147.
127. A. Loupy, B. Tchoubar, Effets de Sel en Chimie Organique et Organometallique, Dunod, Paris, 1988.
128. J. Yarwood, R. Arndt in Molecular Association Vol. 2 (Ed.: R. F. Foster), Academic, New York, 1979, p. 267.
129. Z. G. Soos, D. J. Klein in Molecular Association Vol. 1 (Ed.: R. F. Foster), Academic, New York, 1975, p. 2.
130. C. K. Prout, B. Kamenar in Molecular Complexes Vol. 1 (Ed.: R. F. Foster), Elek, London, 1969, p. 49.
131. R. Rathore, S. V. Lindeman, J. K. Kochi, J. Am. Chem. Soc. 1997, 119, 9393.
132. P. L. Veya, J. K. Kochi, J. Organomet. Chem 1995, 488, CA.
133. H. Kisch, A. Fernandez, Y. Wakatsuki, H. Yamazaki, Z. Naturforsch. 1985, 40b, 292.
134. M. Lemke, F. Knoch, H. Kisch, J. Salbeck, Chem. Ber. 1995, 128, 131.
135. C.-H. Wei, T. M. Bockman, J. K. Kochi, J. Organomet. Chem. 1992, 428, 85.
136. C. Schramm, J. I. Zink, J. Am. Chem. Soc. 1979, 101, 4554.
137. E. K. Kim, J. K. Kochi, J. Am. Chem. Soc. 1991, 113, 4962.
138. S. Brownstein, E. Gabe, F. Lee, A. Piotrowski, Can. J. Chem. 1986, 64, 1661.
139. R. Rathore, S. V. Lindeman, J. K. Kochi, Angew. Chem. Int. Ed. Engl. 1998, 37, 1585.
140. G. I. Borodkin, I. R. Elanov, M. M. Shakirov, V. G. Shubin, J. Phys. Org. Chem. 1993, 6, 153.
141. M. E. Peover, Trans. Faraday Soc. 1966, 62, 3535.
142. J. S. Miller, J. C. Calabrese, A. J. Epstein, J. H. Zhang, W. M. Reiff, J. Chem. Soc, Chem. Commun. 1986, 1026.
143. E. Adman, M. Rosenblum, S. Sullivan, T. N. Margulis, J. Am. Chem. Soc. 1967, 89, 4540.
144. M. Rosenblum, R. W. Fish, C. Bennett, J. Am. Chem. Soc. 1964, 86, 5166.
145. B. Badger, B. Brocklehurst, Trans. Faraday Soc. 1969, 65, 2576, 2582, 2588.
146. J. S. Miller, J. H. Zhang, W. M. Reiff, D. A. Dixon, L. D. Preston, A. H. Reis, Jr, E. Gebert, M. Extine, J. Troup, A. J. Epstein, M. D. Ward, J. Phys. Chem. 1987, 91, 4344.
147. S. M. Hubig, T. M. Bockman, J. K. Kochi, J. Am. Chem. Soc. 1996, 118, 3842.
148. W. Kaiser, Ultrashort Laser Pulses and Applications, Springer, New York, 1988.
149. J.-L. Martin, A. Migus, G. A. Mourou. A. H. Zewail, Ultrafast Phenomena VIII, Springer, New York, 1993.
150. H. Kisch, W. Dümler, C. Chiorboli, F. Scandola, J. Salbeck, J. Daub, J. Phys. Chem. 1992, 96, 10323.
151. S. M. Hubig, unpublished results.
152. R. Criegee, Liebigs Ann. Chem. 1936, 522, 75.
153. R. Criegee, B. Marchand, H. Wannowius, Liebigs Ann. Chem. 1942, 550, 99.
154. R. J. Collin, J. Jones, W. P. Griffith, J. Chem. Soc, Dalton Trans. 1974, 1094.
155. R. L. Clark, E. J. Behrmann, Inorg. Chem. 1975, 14, 1425.
156. J. M. Wallis, J. K. Kochi, J.Am. Chem. Soc. 1988, 110, 8207.
157. G. Wilkinson, M. Rosenblum, M. C. Whiting, R. B. Woodward, J. Am. Chem. Soc. 1952, 74, 2125.
158. E. O. Fischer, F. Röhrscheid, Z. Naturforsch. 1962, 17b, 483.
159. Z. J. Karpinski, J. K. Kochi, J. Organomet. Chem. 1992, 437, 211.
160. Z. J. Karpinski, J. K. Kochi, Inorg. Chem. 1992, 31, 2767.
161. Y. Mugnier, P. Reeb, C. Moise, E. Laviron, J. Organomet. Chem. 1983, 254, 111.
162. D. J. Kuchynka, J. K. Kochi, Inorg. Chem. 1989, 28, 855.
163. W. L. Waltz, O. Hackelberg, L. M. Dorfman, A. Wojcicki, J. Am. Chem. Soc. 1978, 700, 7259.
164. S. P. Church, M. Poliakoff, J. A. Timney, J. J. Turner, J. Am. Chem. Soc. 1981, 103, 7515.
165. H. W. Walker, R. S. Herrick, R. J. Olsen, T. L. Brown, Inorg. Chem. 1984, 23, 3748.
166. M. Itoh, S. Nagakura, Bull. Chem. Soc. Jpn. 1966, 39, 369.
167. R. F. Cozzens, T. A. Gover, J. Phys. Chem. 1970, 74, 3003.
168. J. A. S. Howell, P. M. Burkinshaw, Chem. Rev. 1983, 83, 557.
169. A. Davison, J. E. Ellis, J. Organomet. Chem. 1971, 31, 239.
170. F. Ungvã¢ry, A. Wojcicki, J. Am. Chem. Soc. 1987, 709, 6848.
171. D. J. Kuchynka, C. Amatore, J. K. Kochi, J. Organomet. Chem. 1987, 328, 133.
172. F. G. Bordwell, M. J. Bausch, J. Am. Chem. Soc. 1986, 108, 1979.
173. N. M. Boag, H. D. Kaesz in Comprehensive Organometallic Chemistry Vol. 4 (Eds.: G. Wilkinson, F. G. A. Stone, E. W. Abel), Pergamon, Oxford, 1982, p. 1161.
174. R. E. Lehmann, J. K. Kochi, Organometallics 1991, 10, 190.
175. F. D. Saeva, Top. Curr. Chem 1990, 756, 59.
176. A. N. Nesmeyanov, Yu. A. Chapovsky, I. V. Polovyanyuk, L. G. Makarova, J. Organomet. Chem. 1967, 7, 329.
177. M. D. Curtis, K. B. Shiu, W. M. Butler, J. C. Huffman, J. Am. Chem. Soc. 1986, 108, 3335.
178. A. T. Balaban, C. Bratu, C. N. Rentea, Tetrahedron 1964, 20, 265.
179. V. Wintgens, J. Pouliquen, J. Kossanyi, M. Heintz, Nouv. J. Chim. 1986, 70, 345.
180. A. Nakamura, S. Otsuka, J. Am. Chem. Soc. 1973, 95, 7262 and 1972, 94, 1886.
181. E. Negishi, J. Organomet. Chem. 1976, 108, 281.
182. R. Hunter, J. P. Michael, G. D. Tomlinson, Tetrahedron 1994, 50, 871.
183. T. Nagamura, Pure & Appl. Chem. 1996, 68, 1449.
184. S. Chatterjee, P. D. Davis, P. Gottschalk, M. E. Kurz, B. Sauerwein, X. Yang, G. B. Schuster, J. Am. Chem. Soc. 1990, 112, 6329.
185. G. B. Schuster, Pure & Appl. Chem. 1990, 62, 1565.
186. Cleavage rates for the boron-carbon bond in boranyl radicals have been estimated to exceed k= 1011 s-1 [189, 190].
187. D. Zhu, J. K. Kochi, J. Organomet. Chem. 1999, 580, 295.
188. H. O. House, Acc. Chem. Res. 1976, 9, 59.
189. G. Hallnemo, C. Ullenius, Tetrahedron 1983, 39, 1621.
190. D. Zhu, unpublished results.
191. S. Komiya, T. A. Albright, R. Hoffmann, J. K. Kochi, J. Am. Chem. Soc. 1977, 99, 8440.
192. A. Haim, Prog. Inorg. Chem. 1983, 30, 273.
193. J. C. Polanyi, A. H. Zewail, Acc. Chem. Res. 1995, 28, 119.
194. D. Zhong, A. H. Zewail, J. Phys. Chem. 1998, A102, 4031.
195. W. L. Reynolds, R. W. Lumry, Mechanisms of Electron Transfer, Ronald Press, New York, 1966, p. 12.
196. M. Juillard, M. Chanon, Chem. Rev. 1983, 83, 425.
197. L. Eberson, Electron Transfer Reactions in Organic Chemistry, Springer, New York, 1987, p. 18.
198. The free energy (δGET) for the transfer of an electron from a single donor to an acceptor molecule is given in eV, and thus the Faraday constant is omitted in Eq. 89.
199. D. R. Rosseinsky, Chem. Rev. 1972, 72, 215.
200. I. R. Gould, R. H. Young, L. J. Mueller, A. C. Albrecht, S. Farid, J. Am. Chem. Soc. 1994, 116, 8166.