A unified perspective on the hydrogen atom transfer and proton-coupled electron transfer mechanisms in terms of topographic features of the ground and excited potential energy surfaces as exemplified by the reaction between phenol and radicals

Journal of the American Chemical Society

Volumn 130, Issue 22, 2008, Pages 7000-7010

  Tishchenko, Oksana ^a,b   Truhlar, Donald G ^a   Ceulemans, Arnout ^a   Minh, Tho Nguyen ^b  

^a University of Minnesota ^*  (United States)

^b UNIVERSITY OF LEUVEN   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTRONIC STRUCTURE; HYDROGEN; PHENOLS; VALENCE BANDS;

HYDROGEN ATOM TRANSFER (HAT); PRODUCT BONDING PATTERNS; PROTON-COUPLED ELECTRON TRANSFER (PCET);

POTENTIAL ENERGY SURFACES;

HYDROGEN; PHENOL; RADICAL;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; ELECTRON TRANSPORT; ENERGY; PROTON TRANSPORT; TOPOGRAPHY;

EID: 44449157255     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja7102907     Document Type: Article

References (122)

1. For a recent review, see: Litwinenko, G.; Ingold, K. U. Acc. Chem. Res. 2007, 40, 222.
2. Litwinenko, G.; Ingold, K. U. J. Org. Chem. 2004, 69, 5888.
3. Cannon, R. D. Electron Transfer Reactions; Butterworths: 1980; p 29.
4. Ahrens, B.; Davidson, M. G.; Forsyth, V. T.; Mahon, M. F.; Johnson, A. L.; Mason, S. A.; Price, R. D.; Raithby, P. R. J. Am. Chem. Soc. 2001, 123, 9164.
5. (a) See e.g.; Hammes-Schiffer, S. Acc. Chem. Res. 2001, 34, 273.
6. (b) Mayer, J. M. Annu. Rev. Phys. Chem. 2004, 55, 363.
7. Cukier, R.; Nocera, D. G. Annu. Rev. Phys. Chem. 1998, 49, 337.
8. Roth, J. P.; Lovell, S.; Mayer, J. M. J. Am. Chem. Soc. 2000, 122, 5486.
9. Luzhkov, V. B. Chem. Phys. 2005, 314, 211.
10. Costentin, C.; Evans, D. H.; Robert, M.; Saveat, J.-M.; Singh, P. S. J. Am. Chem. Soc. 2005, 127, 12490.
11. Yuasa, J.; Fukuzumi, S. J. Am. Chem. Soc. 2006, 128, 14281.
12. Skone, J. H.; Soudackov, A. V.; Hammes-Schiffer, S. J. Am. Chem. Soc. 2006, 128, 16655.
13. Hodgkiss, J. M.; Rosenthal, J.; Nocera, D. G. In Hydrogen Transfer Reactions; Hynes, J. T., Klinman, J. P., Limbach, H. H., Schowen, R. L., Eds.; Wiley-VCH: Weinheim, 2007; Vol. 2, p 503.
14. Reece, S. Y.; Hodgkiss, J. M.; Stubbe, J.; Nocera, D. G. Phil. Trans. R. Soc. London, Ser. B 2006, 361, 1351.
15. Rhile, I. J.; Markle, T. F.; Nagao, H.; DiPasquale, A. G.; Lam, O. P.; Lockwood, M. A.; Rotter, K.; Mayer, J. M. J. Am. Chem. Soc. 2006, 128, 6075.
16. Mader, E. A.; Davidson, E. R.; Mayer, J. M. J. Am. Chem. Soc. 2007, 129, 5153.
17. DiLabio, G. A.; Johnson, E. R. J. Am. Chem. Soc. 2007, 129, 6199.
18. Chen, X.; Bu, Y. J. Am. Chem. Soc. 2007, 129, 9713.
19. DiLabio, G. A.; Ingold, K. U. J. Am. Chem. Soc. 2005, 127, 6693.
20. Mayer, J. M.; Hrovat, D. A.; Thomas, J. L.; Borden, W. T. J. Am. Chem. Soc. 2002, 124, 11142.
21. Costentin, C.; Robert, M.; Saveat, J.-M. J. Am. Chem. Soc. 2007, 129, 9953.
22. Ishikita, H.; Soudackov, A. V.; Hammes-Schiffer, S. J. Am. Chem. Soc. 2007, 129, 11146.
23. (a) Sjödin, M.; Styring, S.; Åkermark, B.; Sun, L.; Hammarström, L. J. Am. Chem. Soc. 2000, 122, 3932.
24. (b) Siegbahn, P. E. M.; Eriksson, L.; Himo, F.; Pavlov, M. J. Phys. Chem. B 1998, 102, 10622.
25. (c) Lundqvist, M. J.; Eriksson, L. A. J. Phys. Chem. B 2000, 104, 848.
26. (d) O'Malley, P. J. J. Am. Chem. Soc. 1998, 120, 11732.
27. (e) Maki, T.; Araki, Y.; Ishida, Y.; Onomura, O.; Matsumura, Y. J. Am. Chem. Soc. 2001, 123, 3371. and references therein.
28. (a) Burton, G. W.; Ingold, K. U. Acc. Chem. Res. 1986, 19, 194.
29. (b) Niki, E. Chem. Phys. Lipids 1987, 44, 227.
30. (c) Niki, E.; Noguchi, N. Acc. Chem. Res. 2004, 37, 45.
31. (a) Lin, C.-Y.; Lin, M. C. J. Phys. Chem. 1986, 90, 425.
32. (b) Soot Formation in Combustion - Mechanisms and Models; Bockhorn, H., Ed.; Springer-Verlag: New York, 1993.
33. (c) Horn, C.; Roy, K.; Frank, P.; Just, T. Proc. Int. Symp. Combustion 1998, 27, 321.
34. (d) Ledesma, E. B.; Nelson, P. F.; Mackie, J. C. Proc. Int. Symp. Combustion 2000, 28, 2345.
35. (e) Ross, A. B.; Jones, J. M.; Chaiklangmuang, S.; Pourkashanian, M.; Williams, A.; Kubica, K.; Andersson, J. T.; Kerst, M.; Danihelka, P.; Bartie, K. D. Fuel 2002, 81, 571.
36. (a) Ruedenberg, K.; Schmidt, M. W.; Gilbert, M. M.; Elbert, S. T. Chem. Phys. 1982, 71, 41.
37. (b) Roos, B. O.; Taylor, P. Chem. Phys. 1980, 48, 157.
38. (c) Werner, H.-J.; Knowles, P. J. J. Chem. Phys. 1985, 82, 5053.
39. (a) Hirao, K. Chem. Phys. Lett. 1992, 190, 374.
40. (b) Hirao, K. Chem. Phys. Lett. 1992, 196, 397.
41. (c) Hirao, K. Chem. Phys. Lett. 1993, 201, 59.
42. (d) Hirao, K. Int. J. Quantum Chem. 1992, 26, 517.
43. Nakano, H. J. Chem. Phys. 1993, 99, 7983.
44. Schmidt, M. W.; Baldridge, K. K.; Boatz, J. A.; Elbert, S. T.; Gordon, M. S.; Jensen, J. H.; Koseki, S.; Matsunaga, N.; Nguyen, K. A.; Su, S. J.; Windus, T. L.; Dupuis, M.; Montgomery, J. A. J. Comput. Chem. 1993, 14, 1347.
45. MOLPRO is a package of ab initio programs designed by Werner, H.-J.; Knowles, P. J. version 2002.1, Amos, R. D. et al.
46. (a) The current best estimate of the rotational barrier in phenol is 3.5 kcal/mol. See: Larsen, N. W. J. Mol. Struct. 1986, 144, 83.
47. (b) Zierkiewicz, W.; Michalska, D.; Hobza, P. Chem. Phys. Lett. 2004, 386, 95.
48. (c) Zierkiewicz, W.; Michalska, D.; Černý, J. Hobza Mol. Phys. 2006, 104, 2317.
49. (a) de Heer, M. I.; Mulder, P.; Korth, H.-G.; Ingold, K. U.; Lusztyk, J. J. Am. Chem. Soc. 2000, 122, 2355.
50. (b) Tishchenko, O.; Kryachko, E. S.; Nguyen, M. T. J. Mol. Struct. 2002, 615, 247.
51. (c) Lucarini, M.; Mugnaini, V.; Pedulli, G. F.; Guerra, M. J. Am. Chem. Soc. 2003, 125, 8318.
52. (d) Sun, Y.-M.; Liu, C.-B. Eur. J. Org. Chem. 2004, 120.
53. (a) Lichten, W. Phys. Rev. 1963, 131, 229.
54. (b) O'Malley, T. F. J. Adv. At. Mol. Phys. 1971, 7, 223.
55. (c) Numrich, R. W.; Truhlar, D. G. J. Phys. Chem. 1975, 79, 2745.
56. (d) Delos, J. B.; Thorson, W. R. J. Chem. Phys. 1979, 70, 1774.
57. (e) Spiegelman, F.; Malrieu, J. P. J. Phys. B 1984, 17, 1259.
58. (f) Sidis, V. Adv. Chem. Phys. 1992, 82, 187.
59. (g) Pacher, T.; Cederbaum, L. S.; Köppel, H. Adv. Chem. Phys. 1993, 84, 293.
60. (h) Thürwachter, R.; Halvick, P. J. Chem. Phys. 1997, 221, 33.
61. (i) Nakamura, H.; Truhlar, D. G. J. Chem. Phys. 2002, 117, 5576.
62. (j) Truhlar, D. G. J. Comput. Chem. 2007, 28, 73.
63. Jasper, A. W.; Kendrick, B. K.; Mead, C. A.; Truhlar, D. G. In Modern Trends in Chemical Reaction Dynamics; Yang, X., Liu, K., Eds.; Advanced Series in Physical Chemistry 14; World Scientific: River Edge, NJ, 2004; pp 329-391. See especially pp 339-344
64. Teller, E. J. Phys. Chem. 1937, 41, 109.
65. (a) Atchity, G. J.; Xantheas, S. S.; Ruedenberg, K. J. Chem. Phys. 1991, 95, 1862.
66. (b) Yarkony, D. R. Acc. Chem. Res. 1998, 31, 511.
67. (a) Herzberg, G.; Longuet-Higgins, H. C. Discuss. Faraday Soc. 1963, 35, 77.
68. (b) Longuet-Higgins, H. C. Proc. R. Soc. London, Ser. A 1975, 344, 147,
69. (c) Davidson, E. R. J. Am. Chem. Soc. 1977, 99, 397-402.
70. (d) Mead, C. A.; Truhlar, D. G. J. Chem. Phys. 1979, 70, 2284.
71. (e) Yarkony, D. R. J. Chem. Phys. 1996, 104, 7866.
72. (f) Fukumoto, Y.; Koizumi, H.; Makorh, K. Chem. Phys. Lett. 1999, 313, 283.
73. (g) Zilberg, S.; Haas, Y. J. Am. Chem. Soc. 2002, 124, 10683.
74. (h) Polinger, V. Z.; Huang, R. W.; Dunn, J. L.; Bates, C. A. J. Chem. Phys. 2002, 117, 4340.
75. (i) Rozgonyi, T.; Gonzalez, L. J. Phys. Chem. A 2006, 110, 10251.
76. (a) Allison, T. C.; Lynch, G. J.; Truhlar, D. G.; Gordon, M. S. J. Phys. Chem. 1996, 100, 13575.
77. (b) Truhlar, D. G.; Mead, C. A. Phys. Rev. A 2003, 68, 32501.
78. Navarette, M.; Rangel, C.; Espinosa-Garcia, J.; Corchado, J. C. J. Chem. Theory Comput. 2005, 1, 337.
79. (a) Migani, A.; Sinicropi, A.; Ferre, N.; Cembran, A.; Garavelli, M.; Olivucci, M. Faraday Discuss. 2004, 127, 129.
80. (b) Toniolo, A.; Olsen, S.; Manohar, L.; Martinez, T. J. Faraday Discuss. 2004, 127, 149.
81. Truhlar, D. G. Faraday Discuss. 2004, 127, 242.
82. 42
83. Porter, R. N.; Stevens, R. M.; Karplus, M. J. Chem. Phys. 1968, 49, 5163.
84. Bernasconi, C. F. Adv. Phys. Org. Chem. 1992, 27, 119.
85. Lewis, E. S. In Investigation of Rates and Mechanisms of Reactions, 4th ed.; Bernasconi, C. F., Ed.; Techniques of Chemistry Series 6; John Wiley & Sons: New York; Part I, p 871.
86. Grunwald, E. Thermodynamics of Molecular Species; Wiley: New York, 1997; p 94.
87. 2 interaction involves a third state and is strongest at a position after the saddle point.
88. (a) Varandas, A. J. C.; Brown, E. F.; Mead, C. A.; Truhlar, D. G.; Blais, N. C. J. Chem. Phys. 1987, 86, 6258.
89. (b) Corchado, J. C.; Espinosa-Garcia, J.; Roberto-Neto, O.; Chuang, Y. Y.; Truhlar, D. G. J. Phys. Chem. A 1998, 102, 4899.
90. (c) Biancafort, L.; Jolibois, F.; Olivucci, M.; Robb, A. J. Am. Chem. Soc. 2001, 123, 722.
91. (d) For a recent review see: Carpenter, B. K. Chem. Soc. Rev. 2006, 35, 736.
92. (a) Thompson, T. C.; Truhlar, D. G.; Mead, C. A. J. Chem. Phys. 1985, 82, 2392.
93. (b) Köppel, H. Faraday Discuss 2004, 127, 35.
94. (c) Biancafort, L.; Bearpark, M. J.; Robb, M. A. J. Phys. Chem. A 2007, 111, 2182.
95. More O'Ferrall, R. A. J. Chem. Soc. B 1970, 274.
96. Jencks, W. P. J. Chem. Rev. 1972, 72, 705.
97. Jencks, W. P. J. Chem. Rev. 1985, 85, 511.
98. (a) Albery, W. J.; Kreevoy, M. M. Adv. Phys. Org. Chem. 1978, 16, 87.
99. (b) Kreevoyi, M. M.; Truhlar, D. G. In Investigation of Rates and Mechanisms of Reactions, 4th ed.; Bernasconi, C. F., Ed.; Techniques of Chemistry Series 6; John Wiley and Sons: New York; Part I, p 13.
100. (a) Kreevoy, M. M.; Lee, I.-S. J. Am. Chem. Soc. 1984, 106, 2550.
101. (b) Harris, J. M.; Shafer, S. G.; Moffatt, J. R.; Becker, A. R. J. Am. Chem. Soc. 1929, 101, 3295.
102. (a) Burton, G. W.; Ingold, K. U. J. Am. Chem. Soc. 1981, 103, 6472.
103. (b) Doha, T.; Burton, G. W.; Ingold, K. U. J. Am. Chem. Soc. 1983, 105, 6505.
104. (c) Gilchrist, J.; le, G.; Burton, G. W.; Ingold, K. U. Chem. Phys. 1985, 95, 473.
105. (d) Burton, G. W.; Doba, T.; Gabe, E. J.; Hughes, L.; Lee, F. L.; Prasad, L.; Ingold, K. U. J. Am. Chem. Soc. 1985, 107, 7053.
106. (e) Lucarini, M.; Pedulli, G. F.; Cipollone, M. J. Org. Chem. 1994, 59, 5063.
107. (f) Brinck, T.; Haeberlein, M.; Jonsson, M. J. Am. Chem. Soc. 1997, 119, 4239.
108. 1997, 119, 4245.
109. (g) Wright, J. S.; Carpenter, D. J.; McKay, D. J.; Ingold, K. U. J. Am. Chem. Soc. 1997, 119, 4245.
110. (h) Wright, J. S.; Johnson, E. R.; DiLabio, G. A. J. Am. Chem. Soc. 2001, 123, 1173.
111. (i) Katarina, N. M. J. Mol. Struct. THEOCHEM 2007, 818, 141.
112. (a) McDonald, J. D.; LeBreton, P. R.; Lee, Y. T.; Herschbach, D. R. J. Chem. Phys. 1972, 56, 769.
113. (b) Truhlar, D. G.; Dixon, D. A. In Atom-Molecule Collisions Theory; Bernstein, R. B., Ed.; Plenum: New York, 1979; p 595.
114. (a) Sobolewski, A. L.; Domcke, W.; Dedonder-Lardeux, C.; Jouvet, C. Phys. Chem. Chem. Phys. 2002, 4, 1093.
115. (b) Abe, M.; Ohtsuki, Y.; Fujimura, Y.; Lan, Z.; Domcke, W. J. Chem. Phys. 2006, 124, 224316.
116. Benson, S. W. Thermochemical Kinetics, 2nd ed.; Wiley Interscience: New York, 1976; p 156.
117. Lingwood, M.; Hammond, J. R.; Hrovat, D. A.; Mayer, J. M.; Borden, W. T. J. Chem. Theory Comput. 2006, 2, 740.
118. (a) London, F. Z. Elektrochem. 1929, 35, 552.
119. (b) Hirschfelder, J. O.; Eyring, H.; Rosen, N. J. Chem. Phys. 1936, 4, 121.
120. (c) Yasumori, I. Bull. Chem. Soc. Jpn. 1959, 32, 1110.
121. (d) Porter, R. N.; Karplus, M. J. Chem. Phys. 1964, 40, 1105.
122. (e) Shaik, S.; Shurki, A. Angew. Chem., Int. Ed. 1999, 38, 586.