Concerted proton-electron transfer in the oxidation of hydrogen-bonded phenols

Journal of the American Chemical Society

Volumn 128, Issue 18, 2006, Pages 6075-6088

  Rhile, Ian J ^a   Markle, Todd F ^a   Nagao, Hirotaka ^a   DiPasquale, Antonio G ^a   Lam, Oanh P ^a   Lockwood, Mark A ^a   Rotter, Katrina ^a   Mayer, James M ^a  

^a UNIVERSITY OF WASHINGTON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTROCHEMISTRY; HYDROGEN BONDS; ISOTOPES; PHENOXY RESINS; PROTONS; RATE CONSTANTS;

HETEROGENEOUS ELECTRON TRANSFER; PROTON-COUPLED ELECTRON TRANSFER (PCET) PROCESS; PYRIDINE; ZWITTERIONS;

PHENOLS;

AMINE; AMPHOLYTE; HYDROGEN; IMIDAZOLE; OXIDIZING AGENT; PHENOL DERIVATIVE; PLATINUM; PYRIDINE;

ARTICLE; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; ELECTROCHEMISTRY; ELECTRODE; ELECTRON TRANSPORT; FORCE; HYDROGEN BOND; OXIDATION; OXIDATION REDUCTION POTENTIAL; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; REACTION ANALYSIS; REACTION TIME; STRUCTURE ANALYSIS; SYNTHESIS; TEMPERATURE DEPENDENCE; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; ELECTRONS; HYDROGEN BONDING; KINETICS; MODELS, CHEMICAL; OXIDATION-REDUCTION; PHENOLS; POTENTIOMETRY; PROTONS; SPECTROPHOTOMETRY, ULTRAVIOLET; THERMODYNAMICS;

EID: 33646592867     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja054167+     Document Type: Article

References (192)

1. Cukier, R. I.; Nocera, D. G. Annu. Rev. Phys. Chem. 1998, 49, 337-369.
2. Mayer, J. M. Annu. Rev. Phys. Chem. 2004, 55, 363-390.
3. For an example, see: Chen, K.; Hirst, J.; Camba, R.; Bonagura, C. A.; Stout, C. D.; Burgess, B. K.; Armstrong, F. A. Nature 2000, 405, 814-817.
4. Costentin, C.; Evans, D. H.; Robert, M.; Savéant, J.-M.; Singh, P. S. J. Am. Chem. Soc. 2005, 127, 12490-12491.
5. 4 that CPET be used to specifically refer to concerted processes.
6. (a) Free Radicals; Kochi, J. K., Ed.; Wiley: New York, 1973.
7. (b) Mayer, J. M. Acc. Chem. Res. 1998, 31, 441-450.
8. (a) Biczók, L.; Gupta, N.; Linschitz, H. J. Am. Chem. Soc. 1997, 119, 12601.
9. (b) Gupta, N.; Linschitz, H. J. Am. Chem. Soc. 1997, 119, 6384.
10. (a) Magnuson, A.; Berglund, H.; Korall, P.; Hammarström, L.; Åkermark, B.; Styring, S.; Sun, L. J. Am. Chem. Soc. 1997, 119, 10720-5.
11. (b) Sjödin, M.; Styring, S.; Åkermark, B.; Sun, L.; Hammarström, L. J. Am. Chem. Soc. 2000, 122, 3932-3936.
12. (c) Sjödin, M.; Styring, S.; Wolpher, H.; Xu, Y.; Sun, L.; Hammarström, L. J. Am. Chem. Soc. 2005, 127, 3855-3863.
13. (d) Sjödin, M.; Ghanem, R.; Polivka, T.; Pan, J.; Styring, S.; Sun, L.; Sundström, V.; Hammarström, L. Phys. Chem. Chem. Phys. 2004, 6, 4851-4858.
14. Reece, S. Y.; Nocera, D. G. J. Am. Chem. Soc. 2005, 127, 9448-9458.
15. (a) Shukla, D.; Young, R. H.; Farid, S. J. Phys. Chem. A 2004, 108, 10386-10394.
16. (b) Turro, C.; Chang, C. K.; Leroi, G. E.; Cukier, R. I.; Nocera, D. G. J. Am. Chem. Soc. 1992, 114, 4013.
17. (c) Chang, M. C. Y.; Yee, C. S.; Nocera, D. G.; Stubbe, J. J. Am. Chem. Soc. 2004, 126, 16702-16703.
18. (d) Lehmann, M. W.; Evans, D. H. J. Phys. Chem. B 2001, 105, 8877-8884.
19. (e) Mayer, J. M.; Hrovat, D.; Thomas, J. L.; Borden, W. T. J. Am. Chem. Soc. 2002, 124, 11142-11147.
20. (f) Anglada, J. M. J. Am. Chem. Soc. 2004, 126, 9809-9820.
21. (g) Weatherly, S. C.; Yang, I. V.; Armistead, P. A.; Thorp, H. H. J. Phys. Chem. B. 2003, 107, 372-378.
22. (h) Stubbe, J.; Nocera, D. G.; Yee, C. S.; Chang, M. C. Y. Chem. Rev. 2003, 105, 2167-2201.
23. (i) DiLabio, G. A.; Ingold, K. U. J. Am. Chem. Soc. 2005, 127, 6693-6699.
24. (j) Huynh, M. H. V.; Meyer, T. J. Proc. Natl. Acad Sci. U.S.A. 2004, 101, 13138-13141.
25. (k) Meyer, T. J.; Huynh, M. H. V. Inorg. Chem. 2003, 42, 8140-8160.
26. (a) Kojima, T.; Sakamoto, T.; Matsuda, Y.; Ohkubo, K.; Fukuzumi, S. Angew. Chem., Int. Ed. 2003, 42, 4951.
27. (b) Haddox, R. M.; Finklea, H. O. J. Electroanal. Chem. 2003, 550-557, 351.
28. (a) Stubbe, J.; van der Donk, W. A. Chem. Rev. 1998, 98, 705-762.
29. (b) Pesavento, R. P.; van der Donk, W. A. Adv. Protein Chem. 2001, 58, 317-385.
30. (a) Ehrenberg, A.; Reichard, P. J. Biol. Chem. 1972, 247, 3485-3488.
31. (b) Sjöberg, B.-M.; Reichard, P.; Gräslund, A.; Ehrenberg, A. J. Biol. Chem. 1978, 253, 6863-6865.
32. (c) Sahlin, M.; Gräslund, A.; Ehrenberg, A.; Sjöberg, B.-M. J. Biol. Chem. 1982, 257, 366-369.
33. (d) Griepenburg, U.; Lassmann, G.; Auling, G. Free Radical Res. 1996, 26, 473-481.
34. (a) Barry, B. A.; El-Deeb, M. K.; Sandusky, P. O.; Babcock, G. J. Biol. Chem. 1990, 265, 20139-20143.
35. (b) Barry, B. A.; Babcock, G. T. Proc. Natl. Acad. Sci. U.S.A. 1987, 84, 7099-7103.
36. (a) Tsai, A.-L.; Kulmacz, R. J.; Palmer, G. J. Biol. Chem. 1995, 270, 10503-10508.
37. (b) Tsai, A.-L.; Palmer, G.; Kulmacz, R. J. J. Biol. Chem. 1992, 276, 17753-17759.
38. (c) Tsai, A. L.; Palmer, G.; Xiao, G.; Swinney, D. C.; Kulmacz, R. J. J. Biol. Chem. 1998, 273, 3888.
39. (d) Hsi, L. C.; Hoganson, C. W.; Babcock, G. T.; Smith, W. L. Biochem. Biophys. Res. Commun. 1994, 202, 1592-1598.
40. (a) Ferguson-Miller, S.; Babcock, G. T. Chem. Rev. 1996, 96, 2889-2907.
41. (b) Gamelin, D. R.; Randall D. W.; Hay, M. T.; Houser, R. P.; Mulder, T. C.; Canters, G. W.; de Vries, S.; Tolman, W. B.; Lu, Y.; Solomon, E. I. J. Am. Chem. Soc. 1998, 120, 5246-5263 and references therein.
42. (c) Proshlyakakov, D. A.; Pressler, M. A.; DeMaso, C.; Leykam, J. F.; DeWitt, D. L.; Babcock, G. T. Science 2000, 290, 1588-1591.
43. Whittaker, M. M.; Whittaker, J. W. J. Biol. Chem. 1990, 265, 9610-9613.
44. (a) Janes, S. M.; Mu, D.; Wemmer, D.; Smith, A. J.; Kaur, S.; Maltby, D.; Burlingame, A. L.; Klinman, J. P. Science 1990, 248, 981-987.
45. (b) Janes, S. M.; Palcic, M. M.; Seaman, C. H.; Smith, A. J.; Brown, D. E.; Dooley, D. M.; Mure, M.; Klinman, J. P. Biochemistry 1992, 31, 12147-12154.
46. (c) Cooper, R. A.; Knowles, P. F.; Brown, D. E.; McGuirl, M. A.; Dooley, D. M. Biochem. J. 1992, 288, 337-340.
47. (d) Brown, D. E.; McGuirl, M. A.; Dooley, D. M.; Janes, S. M.; Mu, D.; Klinman, J. P. J. Biol. Chem. 1991, 266, 4049-4051.
48. (e) Mu, D.; Janes, S. M.; Smith, A. J.; Brown, D. E.; Dooley, D. M.; Klinman, J. P. J. Biol. Chem. 1992, 267, 7979-7982.
49. (a) Tommos, C.; Babcock, G. T. Biochim. Biophys. Acta 2000, 1458, 199-219.
50. (b) Vrettos; J. S.; Limburg, J.; Brudvig, G. W. Biochim. Biophys. Acta 2001, 1503, 229-245.
51. (c) Renger, G. Biochim. Biophys. Acta 2004, 1655, 195-204.
52. (d) Rappaport, F.; Lavergne, J. Biochim. Biophys. Acta 2001, 1503, 246-259.
53. (e) Nugent, J. H. A.; Rich, A. M.; Evans, M. C. W. Biochim. Biophys. Acta 2001, 1503, 138-146.
54. (f) Kuhne, H.; Brudvig, G. W. J. Phys. Chem. B 2002, 106, 8189-8196.
55. (g) Faller, P.; Goussias, C.; Rutherford, A. W.; Un, S. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 8732-8735.
56. (h) Ferreira, K. N.; Iverson, T. M.; Maghlaoui, K.; Barber, J.; Iwata, S. Science 2004, 303, 1831-1838.
57. Zouni, A.; Witt, H.-T.; Kern, J.; Fromme, P.; Krauss, N.; Saenger, W.; Orth, P. Nature 2001, 409, 739-743.
58. j) Rhee, K.-H.; Morris, E. P.; Barber, J.; Kuhlbrandt, W. Nature 1998, 396, 283-286.
59. (k) Haumann, M.; Mulkidjanian, A.; Junge, W. Biochemistry 1999, 38, 1258-1267.
60. Kálmán, L.; LoBrutto, R.; Allen, J. P.; Williams, J. C. Nature 1999, 402, 696-699.
61. Petrouleas, V.; Koulougliotis, D.; Ionnidis, N. Biochemistry 2005, 44, 6723-6728.
62. Graige, M. S.; Paddock, M. L.; Bruce, J. M.; Feher, G.; Okamura, M. Y. J. Am. Chem. Soc. 1996, 118, 9005-9016.
63. (a) Page, C. C.; Moser, C. C.; Chen, C.; Dutton, L. Nature 1999, 402, 47-5217.
64. (b) Barbara, P. F.; Meyer, J. T.; Ratner, M. A. J. Phys. Chem. 1996, 100, 13148-13168.
65. Roth, J. P.; Yoder, J. C.; Won, T.-J.; Mayer, J. M. Science 2001, 294, 2524-2526.
66. (a) Swalina, C.; Pak, M. V.; Hammes-Schiffer, S. Chem. Phys. Lett. 2005, 404, 394-399.
67. (b) Hammes-Schiffer, S.; Iordanova, N. Biochim. Biophys. Acta 2004, 1655, 29-36.
68. (c) Hammes-Schiffer, S. Acc. Chem. Res. 2001, 34, 273-281.
69. (d) Hammes-Schiffer, S. ChemPhysChem 2002, 33-42.
70. (e) Cukier, R. I. J. Phys. Chem. B 2002, 106, 1746-1757.
71. (f) Georgievskii, Y.; Stuchebrukhov, A. A. J. Chem. Phys. 2000, 113, 10438-10450.
72. (g) Kuznetsov, A. M.; Ulstrup, J. Can. J. Chem. 1999, 77, 1085-1096.
73. (h) Krishtalik, L. I. Biochim. Biophys. Acta 2000, 1458, 6-27.
74. (i) References 1 and 2.
75. Rhile, I. J.; Mayer, J. M. J. Am. Chem. Soc. 2004, 126, 12718-12719.
76. (a) Talley J. J.; Evans, I. A. J. Org. Chem. 1984, 49, 5267-5269.
77. (b) Gomberg, N.; Nishida, D. J. Chem. Soc. 1922, 190-207.
78. (c) Mandell, L.; Piper, J. V.; Pesterfield, C. E. J. Org. Chem. 1963, 28, 574-575.
79. Altwicker, E. R. Chem. Rev. 1967, 67, 475-531.
80. Maki, T.; Araki, Y.; Ishida, Y.; Onomura, O.; Matsumura, Y. J. Am. Chem. Soc. 2001, 123, 3371-3372.
81. (a) Tramontini, M.; Angiolini, L. Tetrahedron 1990, 46, 1791-1837.
82. (b) Gevorgyan, G. A.; Agababyan, A. G.; Mndzhoyan, O. L. Usp. Khim. 1984, 53, 971-1013.
83. (c) Tramontini, M. Synthesis 1973, 703-775.
84. (d) House, H. O. Modern Synthetic Reactions, 2nd ed.; W. A. Benjamin: New York, 1972; p 654.
85. (e) See also refs 33a and 39.
86. Sparfel, D.; Baranne-Lafont, J.; Cuong, N. K.; Capdevielle, P.; Maumy, M. Tetrahedron 1990, 46, 803-814.
87. (a) Benisvy, L.; Bill, E.; Blake, A. J.; Collison, D.; Davies, E. S.; Garner, C. D.; Guindy, C. I.; McInnes, E. J. L.; McArdle, G.; McMaster, J.; Wilson, C.; Wolowska, J. Dalton Trans. 2004, 3647-3653.
88. (b) Benisvy, L.; Bittl, R.; Bothe, E.; Garner, C. D.; McMaster, J.; Ross, S.; Teutloff, C.; Neese, F. Angew. Chem., Int. Ed. 2005, 44, 5314-5317.
89. Inoue, Y.; Nakano, T.; Tanaka, H.; Kashiwa, N.; Fujita, T. Chem. Lett. 2001, 1060-1061.
90. (a) Stolow, A. Annu. Rev. Phys. Chem. 2003, 54, 89-119.
91. (b) LeGourrierec, D.; Kharlanov, V.; Brown, R. G.; Rettig, W. J. Photochem. Photobiol. A 1998, 117, 209-216.
92. (c) Braeuer, M.; Mosquera, M.; Perez-Lustres, J. L.; Rodriguez-Prieto, F. J. Phys. Chem. A 1998, 102, 10736-10745.
93. (a) In Mannich bases, the range of O- - -N distances across the hydrogen bond is 2.56-2.71 Å: Koll, A.; Wolschann, P. Monatsh. Chem. 1996, 127, 475-486.
94. (b) Imidazoles, 2.55-2.60 Å: Foces-Foces, C.; Llames-Saiz, A. L.; Claramunt, R. M.; Cabildo, P.; Elguero, J. J. Mol. Struct. 1998, 440, 193-202.
95. Benisvy, L.; Blake, A. J.; Collison, D.; Davies, E. S.; Garner, C. D.; McInnes, E. J. L.; McMaster, J.; Whittaker, G.; Wilson, C. J. Chem. Soc., Dalton Trans. 2003, 1975-1985.
96. (c) Pyridines, 2.54-2.56 Å: Shu, Wenmaio; Valiyaveettil, S. Chem. Commun. 2002, 1350-1351.
97. Kaczmarek, L.; Balicki, R.; Lipowski, J.; Borowicz, P.; Grabowska, A. J. Chem. Soc., Perkin Trans. 2 1994, 1603-1610.
98. 33a-c,75
99. (a) Pimentai, G. C.; McClellan, A. L. The Hydrogen Bond; Freeman: New York, 1960.
100. (b) Frey, P. A. Magn. Reson. Chem. 2001, 39, S190-S198.
101. (c) Gilli, P.; Bertolasi, V.; Gilli, G. J. Am. Chem. Soc. 2000, 122, 10405-10417.
102. Silverstein, R. M.; Bassler, G. C.; Morrill, T. C. Spectrometric Identification of Organic Compounds, 5th ed.; Wiley: New York, 1991; (a) p 184 and (b) pp 306-311.
103. Silverstein, R. M.; Bassler, G. C.; Morrill, T. C. Spectrometric Identification of Organic Compounds, 5th ed. (b) p 306-311.
104. Rozwadowski, Z.; Majeewski, E.; Dziembowska, T.; Hansen, P. J. Chem. Soc., Perkin Trans. 2 1999, 2809-2817.
105. Gilli, G.; Belluci, F.; Ferretti, V.; Bertolasi, V. J. Am. Chem. Soc. 1989, 111, 1023-1028.
106. a2 of succinic acid in MeCN is 29.0.
107. (a) Koll, A.; Wolschann, P. Monatsh. Chem. 1999, 130, 983-1001.
108. (b) Przeslawska, M.; Koll, A.; Witanowski, M. J. Phys. Org. Chem. 1999, 12, 486-492.
109. (c) Teitelbaum, A. B.; Derstuganova, K. A.; Shishkina, N. A.; Kudryavtseva, L. A.; Bel'skii, V. E.; Ivanov, B. E. Bull. Acad. Sci. USSR, Div. Chem Sci. (Engl. Transl.) 1980, 558-562;
110. Izv. Akad. Nauk SSSR, Ser. Khim. 1980, 803-808.
111. max < 430 nm.
112. (b) Popp, G. J. Org. Chem. 1972, 37, 3058-3062.
113. (c) Lapachev, V.; Stekhova, S.; Mamaev, V. Monatsh. Chem. 1987, 118, 669-670.
114. (a) Woon, T. C.; Dicken, C. M.; Bruice, T. C. J. Am. Chem. Soc. 1986, 108, 7990-7995.
115. (b) Pokhedenko, V. D.; Khizhny, V. A.; Koshechko, V. G.; Samarskii, V. A. Theor. Exp. Chem. (Engl. Transl.) 1975, 11, 489-493;
116. max (nm, MeCN) = 316, 628 nm (but no ε's).
117. (a) Xie, C.; Lahti, P. M. Tetrahedron Lett. 1999, 40, 4305-4308.
118. (b) Xie, C.; Lahti, P. M.; George, C. Org. Lett. 2000, 2, 3417-3420.
119. Sorensen, S. P.; Bruning W. H. J. Am. Chem. Soc. 1973, 95, 2445-2451.
120. (a) Swaddle, T. W. Chem. Rev. 2005, 105, 2573-2608.
121. (b) Bard, A. J.; Faulkner, L. R. Electrochemical Methods: Fundamentals and Applications, 2nd ed.; John Wiley and Sons Inc.: New York, 2001.
122. pa = 1, as is the case here, the value of α is typically close to 0.5. Simulated CVs using α = 0.4, 0.5, and 0.6 showed no significant difference.
123. DigiSim software is a product of Bioanalytical Systems, Inc. (http:// www.bioanalytical.com/products/ec/digisim/index.html).
124. (a) Thomas, F.; Jarjayes, O.; Jamet, H.; Hamman, S.; Saint-Aman, E.; Duboc, C.; Pierre, J.-L. Angew. Chem. 2004, 116, 604-607;
125. Angew. Chem., Int. Ed. 2004, 43, 594-597.
126. (b) Rhile, I. J.; Mayer, J. M. Angew. Chem. 2005, 105, 1624-1625;
127. Angew. Chem., Int. Ed. 2005, 44, 1598-1599.
128. (a) Bordwell, F. G.; Cheng, J.-P. J. Am. Chem. Soc. 1991, 113, 1736-1743.
129. (b) Cf: Williams, L. L.; Webster, R. D. J. Am. Chem. Soc. 2004, 126, 12441-12450.
130. (c) For aqueous electrochemistry, see: Li, C.; Hoffman, M. Z. J. Phys. Chem. B 1999, 103, 6653-6656.
131. See the Supporting Information of ref 24.
132. (a) Noel, M.; Vasu, K. I. Cyclic Voltammetry and the Frontiers of Electrochemistry; Aspect: London, 1990; pp 141-143.
133. (b) Braga, T. G.; Wahl, A. C. J. Phys. Chem. 1985, 89, 5822-5828.
134. (c) Chan, M.-S.; Wahl, A. C. J. Phys. Chem. 1978, 82, 2542-2549.
135. Binstead, R. A.; Zuberbühler, A. D.; Jung, B. Specfit, version 3.0.36 (32-bit Windows); Spectrum Software Associates: Chapel Hill, NC, 2004.
136. ‡)/RT]; κ is assumed to be 1.
137. +/0.
138. (b) Connelly, N. G.; Geiger, W. E. Chem. Rev. 1996, 96, 877-910.
139. March, J. Advanced Organic Chemistry, 4th ed.; Wiley: New York, 1992; p 76.
140. Kanamori, D.; Furukawa, A.; Okamura, T.; Yamamoto, H.; Ueyama, N. Org. Biomol. Chem. 2005, 3, 1453-1459.
141. 3ArOH, hydrogen bonding to solvent is a small effect. For instance, 2,6-di-tert-butyl-4-methylphenol (BHT) is only 14% hydrogen-bonded in MeCN: Wren, J. J.; Lenthen, P. M. J. Chem. Soc. 1961, 2557-2560.
142. Sjödin, M.; Styring, S.; Åkermark, B.; Sun, L.; Hammarström, L. Philos. Trans. R. Soc. London B 2002, 357, 1471-1479.
143. (a) Lucarini, M.; Pedulli, G. F.; Guerra, M. Chem. Eur. J. 2004, 10, 933-939.
144. (b) Lucarini, M.: Mugnaini, V.; Pedulli, G. F.; Guerra, M. J. Am. Chem. Soc. 2003, 125, 8318-8329.
145. (c) Amorati, R.; Lucarini, M.; Mugnaini, V.; Pedulli, G. F. J. Org. Chem. 2003, 68, 5198-5204.
146. -1. Foti, M. C.; Barclay, L. R. C.; Ingold, K. U. J. Am. Chem. Soc. 2002, 124, 12881-12888.
147. a data from refs 38 and 60).
148. (a) Reference 48a.
149. a values in DMSO and MeCN is taken as 9.5 units according to the following: Chantooni, M. K., Jr.; Kolthoff, I. M. J. Phys. Chem. 1976, 80, 1306-1310.
150. (a) Brede, O.; Hermann, R.; Karakostas, N.; Naumov, S. Phys. Chem. Chem. Phys. 2004, 6, 5184-5188.
151. (b) Ganapathi, M. R.; Hermann, R.; Naumov, S.; Brede, O. Phys. Chem. Chem. Phys. 2000, 2, 4947-4955.
152. (a) Rospenk, M.; Fritsch, J.; Zundel, G. J. Phys. Chem. 1984, 88, 321-323.
153. (b) Koll, A.; Rospenk, M.; Sobczyk, L. J. Chem. Soc., Faraday Trans. 1 1981, 77, 2309-2314.
154. (c) Rospenk, M. J. Mol. Struct. 1990, 221, 109-114.
155. Bell, R. P. The Proton in Chemistry; Cornell University Press: Ithaca, NY, 1973.
156. Eberson, L. Electron Transfer Reactions in Organic Chemistry; Springer-Verlag: New York, 1987;
157. (a) pp 77-79,
158. (b) pp 51-52,
159. (c) p 27, and
160. (d) pp 30-34 (using the radii in ref 71).
161. (a) Buhks, E.; Bixon, M.; Jortner, J. J. Phys. Chem. 1981, 85, 3763.
162. (b) Smaller secondary isotope effects have been observed for related electron transfers, e.g. Gould, I. R.; Farid, S. J. Am. Chem. Soc. 1988, 110, 7883-5.
163. ET1 would have to be off by more than 0.3 V. Thus, the use of the Eyring equation here is a conservative (worst-case) choice for this argument, (a) Hamann, T. W.; Gstrein, F.; Brunschwig, B. S.; Lewis, N. S. J. Am. Chem. Soc. 2005, 127, 13949-1 3954.
164. 67a-d,71 (a) Marcus, R. A.; Sutin, N. Biochim. Biophys. Acta 1985, 811, 265-322.
165. (b) Sutin, N. Prog. Inorg. Chem. 1983, 30, 441-499.
166. (c) Sutin, N. Acc. Chem. Res. 1982, 15, 275-282.
167. (d) Nelsen, S. F.; Pladziewicz, J. R. Acc. Chem. Res. 2002, 35, 247-254.
168. Cf.: (a) McClelland, R. A.; Kanagasabapathy, J. V. M.; Banait, N. S.; Steenken, S. J. Am. Chem. Soc. 1992, 114, 1816-1823.
169. (b) de Carvalho, I. M. M.; Gehlen, M. H. J. Photochem. Photobiol. A: Chem. 1999, 122, 109-113.
170. (c) Kikuchi, K.; Sato, C.; Watabe, M.; Ikeda, H.; Takahashi, Y.; Miyashi, T. J. Am. Chem. Soc. 1993, 115, 5180-5184.
171. (a) Fang, Y.; Liu, L.; Feng, Y.; Li, X.; Guo, Q. J. Phys. Chem. A 2002, 106, 4669-4678.
172. (b) Feng, Y.; Liu, L.; Fang, Y.; Guo, Q. J. Phys. Chem. A 2002, 106, 11518-11525.
173. (c) Wang, Y.; Eriksson, L. A. Int. J. Quantum Chem. 2001, 83, 220-229.
174. (d) O'Malley, P. J. J. Am. Chem. Soc. 1998, 120, 11732-11737.
175. (e) Kim, H.; Green, R. J.; Qian, J.; Anderson, S. L. J. Chem. Phys. 2000, 112, 5717-5721.
176. + species in solution has been calculated in ref 30b.
177. 70a the distance between proton positions in OH⋯N vs O⋯HN tautomers should be 0.56-0.68 Å in a linear hydrogen bond. In the bent structures likely for HOAr-B, the distances should be ∼0.7-0.8 Å.
178. (b) CRC Handbook of Chemistry and Physics, 54th ed.; Weast, R. C., Ed.; CRC Press; Cleveland, OH, 1973; pp F198-F199.
179. .+ reactions, one of the species on each side of the equation is uncharged; therefore, the correction is zero.
180. (b) Schlesener, C. J.; Amatore, C.; Kochi, J. K. J. Am. Chem. Soc. 1984, 106, 3567-3577.
181. -1.
182. Kowert, B. A.; Marcoux, L.; Bard, A. J. J. Am. Chem. Soc. 1972, 94, 5538-5550.
183. 3+ would also be slightly faster.
184. Markle, T. F.; Rhile, I. J.; Nagao, H.; DiPasquale, A. G.; Mayer J. M., manuscript in preparation and work in progress.
185. -1 at all temperatures; see, however, the discussion of non-adiabatic character below.
186. (a) Marcus, R. A. J. Phys. Chem. 1963, 67, 853-857.
187. (b) Fu, Y.; Swaddle, T. W. J. Am. Chem. Soc. 1997, 119, 7137-7144.
188. Newton, M. D.; Sutin, N. Annu. Rev. Phys. Chem. 1984, 35, 437-480 (esp. p 451).
189. Sutin, N. Prog. Inorg. Chem. 1983, 30, 441-498.
190. ‡ to reflect the low probability of reaction, but the values observed, -14 to -17 eu, are modest for a bimolecular process.
191. P) vs T data to eq 15.
192. Zhang, H.; Kwong, F. Y.; Tian, Y.; Chan, K. S. J. Org. Chem. 1998, 63, 6886-6890.