Metal Coordinated Phenoxyl Radicals

Stable Radicals: Fundamentals and Applied Aspects of Odd-Electron Compounds

Volumn , Issue , 2010, Pages 281-316

  Thomas, Fabrice ^a  

^a UNIV GRENOBLE ALPES   (France)

Author keywords

"valence tautomerism"; Charge transfer (CT); Overlap between the and selected d orbitals in octahedral and square planar complexes; Oxidative behavior of H3 APL15 in the presence of metal; Stable Radicals: Fundamentals and Applied Aspects of Odd Electron Compounds; Structure of non coordinated phenoxyl radicals

Indexed keywords

EID: 77958106389     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9780470666975.ch8     Document Type: Chapter

References (141)

1. R. Pummerer, and F. Frankfurter, Chem. Ber., 47, 1479 (1914).
2. E. R. Altwicker, Chem. Rev., 67, 475-531 (1967).
3. A. Ehrenberg, and P. Reichard, J. Biol. Chem., 247, 3485-3488 (1972).
4. J. L. Pierre, Chem. Soc. Rev., 29, 251-257 (2000).
5. J. Stubbe, and W. Van Der Donk, Chem. Rev., 98, 705-762 (1998).
6. C. D. Borman, C. G. Saysell, A. Sokolowski, et al., Coord. Chem. Rev., 190-192, 771-779 (1999).
7. M. J. McPherson, M. R. Parsons, R. K. Spooner, and C. M. Wilmot, Galactose Oxidase, in Handbook of metalloproteins (eds A. Messerschmidt, R. Huber, K. Wieghardt, and T. Poulos), John Wiley and Sons Ltd, Chichester, 2001.
8. J. W. Whittaker, Chem. Rev., 103, 2347-2363 (2003).
9. B. A. Jazdzewski, and W. B. Tolman, Coord. Chem. Rev., 200-202, 633-685 (2000).
10. H. J. Krüger, Angew. Chem. Int. Ed., 38, 627-631 (1999).
11. S. Itoh, M. Taki, and S. Fukuzumi, Coord. Chem. Rev., 198, 3-20 (2000).
12. P. Chaudhuri, and K. Wieghardt, Prog. Inorg. Chem., 50, 151-216 (2001).
13. F. Thomas, Eur. J. Inorg. Chem., 2379-2404 (2007).
14. C. G. Pierpont, and R. M. Buchanon, Coord. Chem. Rev., 38, 45-87 (1981).
15. C. G. Pierpont, and C. W. Lange, Prog. Inorg. Chem., 41, 331-442 (1994).
16. C. G. Pierpont, Coord. Chem. Rev., 216-217, 99-125 (2001).
17. B. Adam, E. Bill, E. Bothe, et al., Chem. Eur. J., 3, 308-319 (1997).
18. S. Bruni, A. Caneschi, F. Cariati, et al., J. Am. Chem. Soc., 116, 1388-1394 (1994).
19. A. J. Bard, and H. Lund (Eds), Encyclopedia of Electrochemistry of the Elements, vol. XI, Organic section, Marcel Dekker, New York, 1976.
20. D. Zurita, I. Gautier-Luneau, S. Ménage, et al., J. Biol. Inorg. Chem., 2, 46-55 (1997).
21. Y. Shimazaki, S. Huth, S. Hirota, and O. Yamauchi, Inorg. Chim. Acta, 331, 168-177 (2002).
22. A. Philibert, F. Thomas, C. Philouze, et al., Chem. Eur. J., 9, 3803-3812 (2003).
23. F. Michel, F. Thomas, S. Hamman, et al., Chem. Eur. J., 10, 4115-4125 (2004).
24. F. G. Bordwell, and J. P. Cheng, J. Am. Chem. Soc., 113, 1736-1743 (1991).
25. In order to facilitate comparison between the systems, all electrochemical potentials are given relative to the Fc+/Fc reference. When potentials are reported vs other standards, corrections are applied according to the following references: N. G. Connelly, and W. E. Geiger, Chem. Rev., 96, 877-910 (1996); V. V. Pavlishchuk, and A. W. Addison, Inorg. Chim. Acta, 298, 97-102 (2000). Differences in solvent, electrolyte, ionic strength may, however, complicate the comparison.
26. R. D. Webster, Electroch. Commun., 5, 6-11 (2003).
27. I. M. Kolthoff, and M. K. Chantooni. J. Am. Chem. Soc., 87, 4428-4436 (1965).
28. T. Maki, Y. Araki, Y. Ishida, et al., J. Am. Chem. Soc., 123, 3371-3372 (2001).
29. J. M. Mayer, and I. J. Rhile, J. Am. Chem. Soc., 126, 12718-12719 (2004).
30. I. J. Rhile, T. F. Markle, H. Nagao, et al., J. Am. Chem. Soc., 128, 6075-6088 (2006).
31. M. Sjödin, T. Irebo, J. E. Utas, et al., J. Am. Chem. Soc., 128, 13076-13083 (2006).
32. C. Constentin, M. Robert, and J. M. Savéant, J. Am. Chem. Soc., 128, 4552-4553 (2006).
33. D. E. Williams, Mol. Phys., 16, 145-151 (1969).
34. V. W. Manner, T. F. Markle, J. H. Freudenthal, et al., Chem. Commun., 256-258 (2008).
35. G. G. Aleksandrov, Y. T. Struchkov, D. I. Kalinin, and M. G. Neigauz, Zh. Strukt. Khim., 14, 852-858 (1973).
36. S. Goldschmidt and W. Schmidt, Ber., 55, 3197 (1922).
37. C. D. Cook, C. B. Depathi, and E. S. English, J. Org. Chem., 24, 1356-1358 (1959).
38. T. N. Das, J. Phys. Chem. A, 109, 3344-3351 (2005).
39. J. G. Radziszewski, M. Gil, A. Gorski, et al., J. Chem. Phys., 115, 9733-9738 (2001).
40. S. Itoh, S. Takayama, R. Arakawa, et al., Inorg. Chem., 36, 1407-1416 (1997).
41. A. Y. Bresgunov, A. A. Dubinsky, O. G. Poluektov, et al., Mol. Phys., 75, 1123-1131 (1992).
42. T. Yamaji, I. S. M. Saiful, M. Baba, et al., J. Phys. Chem. A, 111, 4612-4619 (2007).
43. F. Thomas, O. Jarjayes, H. Jamet, et al., Angew. Chem. Int. Ed., 43, 594-597 (2004).
44. L. Benisvy, R. Bittl, E. Bothe, et al., Angew. Chem. Int. Ed., 44, 5314-5317 (2005).
45. See the special issue of Chem. Rev. 103 (6) (2003) devoted to radical metalloenzymes.
46. M. M. Whittaker, P. J. Kersten, D. Cullen, and J. W. Whittaker, J. Biol. Chem., 274, 36226-36232 (1999).
47. N. Ito, S. E. V. Philips, C. Stevens, et al., Nature, 350, 87-90 (1991).
48. N. Ito, S. E. V. Philips, K. D. S. Yadav, and P. F. Knowles, J. Mol. Biol., 794-814 (1994).
49. C. Wright, and A. G. Sykes, J. Inorg. Biochem., 85, 237-243 (2001).
50. M. M. Whittaker, and J. W. Whittaker, J. Biol. Chem., 263, 6074-6080 (1988).
51. M. M. Whittaker, C. A. Ekberg, J. Peterson, et al., J. Mol. Cat. B, 8, 3-15 (2000).
52. D. Rokhsana, D. M. Dooley, and R. K. Szilagyi, J. Am. Chem. Soc., 128, 15550-15551 (2006).
53. M. M. Whittaker, D. P. Ballou, and J. W. Whittaker, Biochemistry, 37, 8426-8436 (1998).
54. B. P. Branchaud, M. P. Montague-Smith, D. J. Kosman, and F. R. Mc Laren, J. Am. Chem. Soc., 64, 798-800 (1993).
55. R. M. Wachter, and B. P. Branchaud, Biochim. Biophys. Acta, 1384, 43-54 (1998).
56. M. Fontecave, and J. L. Pierre, Bull. Soc. Chim. Fr., 133, 653-660 (1996).
57. M. M. Whittaker, and J. W. Whittaker, Biochemistry, 40, 7140-7148 (2001).
58. S. G. Minasian, M. M. Whittaker, and J. W. Whittaker, Biochemistry, 43, 13683-13693 (2004).
59. U. Auerbach, T. Weyhermüller, K. Wieghardt, et al., Inorg. Chem., 32, 508-519 (1993).
60. A. Sokowski, B. Adam, T. Weyhermüller, et al., Inorg. Chem., 36, 3702-3710 (1997).
61. T. K. Paine, T. Weyhermüller, L. D. Slep, et al., Inorg. Chem., 43, 7324-7338 (2004).
62. H. Chun, C. N. Verani, P. Chaudhuri, et al., Inorg. Chem., 40, 4157-4166 (2001).
63. A. Sokolowski, E. Bothe, E. Bill, et al., Chem. Commun., 1671-1672 (1996).
64. J. Müller, A. Kikuchi, E. Bill, et al., Inorg. Chim. Acta, 297, 265-277 (2000).
65. A. dos Anjos, A. J. Bortoluzzi, M. S. B. Caro, et al., J. Braz. Chem. Soc., 17, 1540-1550 (2006).
66. H. Chun, P. Chaudhuri, T. Weyhermüller, and K. Wieghardt, Inorg. Chem., 41, 790-795 (2002).
67. K. S. Min, T. Weyhermüller, and K. Wieghardt, Dalton Trans., 178-186 (2004).
68. T. K. Paine, T. Weyhermüller, E. Bothe, et al., Dalton Trans., 3136-3144 (2003).
69. S. Mukherjee, E. Rentschler, T. Weyhermüller, et al., Chem. Commun., 1828-1829 (2003).
70. S. Mukherjee, T. Weyhermüller, E. Bothe, et al., Dalton Trans., 3842-3853 (2004).
71. J. F. Berry, E. Bill, E. Bothe, et al., Science, 312, 1937-1941 (2006).
72. J. Hockertz, S. Steenken, K. Wieghardt, and P. Hildebrandt, J. Am. Chem. Soc., 115, 11222-11230 (1993).
73. M. D. Snodin, L. Ould-Moussa, U. Wallman, et al., Chem. Eur. J., 5, 2554-2565 (1999).
74. A. K. Nairn, R. Bhalla, S. P. Foxon, et al., J. Chem. Soc., Dalton Trans., 1253-1255 (2002).
75. H. Chun, E. Bill, E. Bothe, et al., Inorg. Chem., 41, 5091-5099 (2002).
76. K. S. Min, T. Weyhermüller, and K. Wieghardt, Dalton Trans., 1126-1132 (2003).
77. H. Chun, T. Weyhermüller, E. Bill, and K. Wieghardt, Angew. Chem. Int. Ed., 40, 2489-2492 (2001).
78. H. Chun, E. Bill, T. Weyhermüller, and K. Wieghardt, Inorg. Chem., 42, 5612-5620 (2003).
79. S. Mukherjee, T. Weyhermüller, E. Bill, et al., Inorg. Chem., 44, 7099-7108 (2005).
80. C. N. Verani, E. Bothe, D. Burdinski, et al., Eur. J. Inorg. Chem., 2161-2169 (2001).
81. U. Beckmann, E. Bill, T. Weyhermüller, and K. Wieghardt, Eur. J. Inorg. Chem., 1768-1777 (2003).
82. A. Dei, D. Gatteschi, C. Sangregorio, et al., Inorg. Chem., 42, 1701-1706 (2003).
83. L. Benisvy, E. Bill, A. J. Blake, et al., Dalton Trans., 3647-3653 (2004).
84. Y. Shimazaki, R. Kabe, S. Huth, et al., Inorg. Chem., 46, 6083-6090 (2007).
85. D. Herebian, P. Ghosh, H. Chun, et al., Eur. J. Inorg. Chem., 1957-1967 (2002).
86. C. N. Verani, S. Gallert, E. Bill, et al., Chem. Commun., 1747-1748 (1999).
87. Y. Shimazaki, S. Huth, S. Karasawa, et al., Inorg. Chem., 43, 7816-7822 (2004).
88. Y. Shimazaki, F. Tani, K. Fului, et al., J. Am. Chem. Soc., 125, 10512-10513 (2003).
89. T. Glaser, M. Heidemeier, R. Frölich, et al., Inorg. Chem., 44, 5467-5482 (2005).
90. O. Rotthaus, O. Jarjayes, C. Perez Del Valle, et al., Chem. Commun., 4462-4464 (2007).
91. L. Benisvy, R. Kannappan, Y. F. Song, et al., Eur. J. Inorg. Chem., 631-633 (2007).
92. O. Rotthaus, O. Jarjayes, F. Thomas, et al., Chem. Eur. J., 12, 2293-2302 (2006).
93. Y. Shimazaki, T. Yajima, F. Tani, et al., J. Am. Chem. Soc., 129, 2559-2568 (2007).
94. T. Storr, E. C. Wasinger, R. C. Pratt, and T. D. P. Stack, Angew. Chem. Int. Ed., 46, 5198-5201 (2007).
95. O. Rotthaus, F. Thomas, O. Jarjayes, et al., Chem. Eur. J., 12, 6953-6962 (2006).
96. P. Chaudhuri, C. N. Verani, E. Bill, et al., J. Am. Chem. Soc., 123, 2213-2223 (2001).
97. K. S. Min, T. Weyhermüller, E. Bothe, and K. Wieghardt, Inorg. Chem., 43, 2922-2931 (2004).
98. J. A. Halfen, V. G. Young Jr, and W. B. Tolman, Angew. Chem. Int. Ed., 35, 1687-1690 (1996).
99. J. A. Halfen, B. A. Jazdzewski, S. Mahapatra, et al., J. Am. Chem. Soc., 119, 8217-8227 (1997).
100. A. Sokolowski, H. Leutbecher, T. Weyhermüller, et al., J. Biol. Inorg. Chem., 2, 444-453 (1997).
101. J. Müller, T. Weyhermüller, E. Bill, et al., Angew. Chem. Int. Ed., 37, 616-619 (1998).
102. E. Bill, J. Müller, T. Weyhermüller, and K. Wieghardt, Inorg. Chem., 38, 5795-5802 (1999).
103. Y. Shimazaki, S. Huth, S. Hirota, and O. Yamauchi, Bull. Chem. Soc. Jpn., 73, 1187-1195 (2000).
104. S. Itoh, M. Taki, H. Kumei, et al., Inorg. Chem., 39, 3708-3711 (2000).
105. M. Taki, H. Hattori, T. Osako, et al., I norg. Chim. Acta, 357, 3369-3381 (2004).
106. F. Michel, S. Hamman, F. Thomas, et al., Chem. Commun., 4122-4124 (2006).
107. Y. Shimazaki, S. Huth, A. Odani, and O. Yamauchi, Angew. Chem. Int. Ed., 39, 1666-1669 (2000).
108. F. Thomas, G. Gellon, I. Gautier-Luneau, et al., Angew. Chem. Int. Ed., 41, 3047-3050 (2002).
109. M. Taki, H. Kumei, S. Nagatomo, et al., Inorg. Chim. Acta, 300-302, 622-632 (2000).
110. F. Michel, S. Torelli, F. Thomas, et al., Angew. Chem. Int. Ed., 44, 438-440 (2005).
111. S. Itoh, M. Taki, S. Takayama, et al., Angew. Chem. Int. Ed., 38, 2774-2776 (1999).
112. A. Mukherjee, F. Lloret, and R. Mukherjee, Inorg. Chem., 47, 4471-4480 (2008).
113. Y. Wang, and T. D. P. Stack, J. Am. Chem. Soc., 118, 13097-13098 (1996).
114. Y. Wang, J. L. Dubois, B. Hedman, et al., Science, 279, 537-540 (1998).
115. R. C. Pratt, and T. D. P. Stack, J. Am. Chem. Soc., 125, 8716-8717 (2003).
116. F. Thomas, O. Jarjayes, C. Duboc, et al., Dalton Trans., 2662-2669 (2004).
117. I. Sylvestre, J. Wolowska, C. A. Kilner, et al., Dalton Trans., 3241-3249 (2005).
118. T. Storr, P. Verma, R. C. Pratt, et al. k, J. Am. Chem. Soc., 130, 15448-15459 (2008).
119. E. Saint-Aman, S. Ménage, J.-L. Pierre, et al., New J. Chem., 393-394 (1998).
120. M. Vaidyanathan, M. Palaniandavar, and R. S. Gopalan, Ind. J. Chem., 42A, 2210-2222 (2003).
121. A. dos Anjos, A. J. Bortoluzzi, B. Szpoganicz, et al., Inorg. Chim. Acta, 358, 3106-3114 (2005).
122. A. dos Anjos, A. J. Bortoluzzi, R. E. H. M. B. Osorio, et al., Inorg. Chem. Comm., 8, 249-253 (2005).
123. R. C. Pratt, and T. D. P. Stack, Inorg. Chem., 44, 2367-2375 (2005).
124. A. K. Nairn, S. J. Archibald, R. Bhalla, et al., Dalton Trans., 1, 172-176 (2006).
125. E. Zueva, P. H. Walton, and J. E. McGrady, Dalton Trans., 1, 159-167 (2006).
126. L. Benisvy, A. J. Blake, D. Collison, et al., Chem. Commun., 1824-1825 (2001).
127. L. Benisvy, A. J. Blake, D. Collison, et al., Dalton Trans., 1975-1985 (2003).
128. L. Benisvy, E. Bill, A. J. Blake, D. Collison, et al., Dalton Trans., 258-267 (2006).
129. P. Chaudhuri, M. Hess, U. Flörke, and K. Wieghardt, Angew. Chem. Int. Ed., 37, 2217-2220 (1998).
130. P. Chaudhuri, M. Hess, T. Weyhermüller, and K. Wieghardt, Angew. Chem. Int. Ed., 38, 1095-1098 (1999).
131. G. Speier, J. Csihony, A. M. Whalen, and C. G. Pierpont, Inorg. Chem., 35, 3519-3524 (1996).
132. T. K. Paine, T. Weyhermüller, K. Wieghardt, and P. Chaudhuri, Dalton Trans., 2092-2101 (2004).
133. P. Chaudhuri, M. Hess, J. Müller, et al., J. Am. Chem. Soc., 121, 9599-9610 (1999).
134. P. Chaudhuri, K. Wieghardt, T. Weyhermüller, et al., Biol. Chem., 386, 1023-1033 (2005).
135. T. Kruse, and T. Weyhermüller, K. Wieghardt, Inorg. Chim. Acta, 331, 81-89 (2002).
136. M. A. Halcrow, L. M. L. Chia, X. Liu, et al., Chem. Commun., 2465-2466 (1998).
137. I. Sylvestre, J. Wolowska, E. J. L. McInnes, et al., Inorg. Chim. Acta, 358, 1337-1341 (2005).
138. O. Séneque, M. Campion, B. Douziech, et al., Dalton Trans., 4216-4218 (2003).
139. A. Sokolowski, J. Müller, T. Weyhermüller, et al., J. Am. Chem. Soc., 119, 8889-8900 (1997).
140. O. Rotthaus, O. Jarjayes, F. Thomas, et al., Dalton Trans., 889-895 (2007).
141. P. Chaudhuri, M. Hess, K. Hildenbrand, et al., Inorg. Chem., 38, 2781-2790 (1999).