Probing quantum and dynamic effects in concerted proton-electron transfer reactions of phenol-base compounds

Journal of Physical Chemistry B

Volumn 116, Issue 1, 2012, Pages 571-584

  Markle, Todd F ^a,b   Tenderholt, Adam L ^a   Mayer, James M ^a  

^a UNIVERSITY OF WASHINGTON   (United States)

^b UPPSALA UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

ATOMS; CONTINUUM MECHANICS; ELECTRON TRANSITIONS; HYDROGEN BONDS; ISOTOPES; MOLECULAR ORBITALS; ORGANIC COMPOUNDS; PHENOLS; POSITIVE IONS; SPHERES; WAVE FUNCTIONS;

AMINE DERIVATIVES; AMINE GROUPS; CONTINUUM THEORY; DONOR-ACCEPTOR DISTANCE; DONOR-ACCEPTORS; DYNAMIC EFFECTS; ENERGY SURFACE; EXPERIMENTAL STUDIES; HEAVY ATOMS; INTRAMOLECULAR HYDROGEN BOND; KINETIC ISOTOPE EFFECTS; MULTI STATE; NITROGEN ATOM; ONE-DIMENSIONAL POTENTIAL; OPTIMIZED STRUCTURES; OVERLAP INTEGRALS; PYRIDYL; RELATIVE RATES; SIMPLIFYING ASSUMPTIONS; TEMPERATURE DEPENDENCE; THEORETICAL RESULT; TRANSFER REACTION; TRANSMISSION FREQUENCIES; VIBRATIONAL STATE; VIBRATIONAL WAVE FUNCTIONS;

PROTONS;

EID: 84855841555     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp2091736     Document Type: Article

References (100)

1. Huynh, M. H. V.; Meyer, T. J. Chem. Rev. 2007, 107, 5004-5064
2. Mayer, J. M. Annu. Rev. Phys. Chem. 2004, 55, 363-390
3. 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, 2006; pp 503-562.
4. Cukier, R. I.; Nocera, D. G. Annu. Rev. Phys. Chem. 1998, 49, 337-369
5. Costentin, C. Chem. Rev. 2008, 108, 2145-2179
6. 2010, 110, PR1-40.
7. The term CPET was coined by: Costentin, C.; Evans, D. H.; Robert, M.; Savéant, J.-M.; Singh, P. S. J. Am. Chem. Soc. 2005, 127, 12490-12491
8. Meyer, T. J.; Huynh, M. H. V.; Thorp, H. H. Angew. Chem., Int. Ed. 2007, 46, 5284-5304
9. Umena, Y.; Kawakami, K.; Shen, J.-R.; Kamiya, N. Nature 2011, 473, 55-61
10. Barry, B. A. J. Photochem. Photobiol., B 2011, 104, 60-71
11. Biczók, L.; Gupta, N.; Linschitz, H. J. Am. Chem. Soc. 1997, 119, 12601
12. Gupta, N.; Linschitz, H. J. Am. Chem. Soc. 1997, 119, 6384
13. Sjödin, M.; Styring, S.; Wolpher, S.; Xu, Y.; Sun, L.; Hammarström, L. J. Am. Chem. Soc. 2005, 127, 3855-3863
14. Sjödin, M.; Irebo, T.; Utlas, J. E.; Lind, J.; Merényi, G.; Åkermark, B.; Hammarström, L. J. Am. Chem. Soc. 2006, 128, 13076-13083
15. Irebo, T.; Reece, S. Y.; Sjodin, M.; Nocera, D. G.; Hammarström, L. J. Am. Chem. Soc. 2007, 129, 15462-15464
16. Irebo, T.; Johansson, O.; Hammarström, L. J. Am. Chem. Soc. 2008, 130, 9194-9195
17. Johannissen, L. O.; Irebo, T.; Sjödin, M.; Johansson, O.; Hammarström, L. J. Phys. Chem. B 2009, 113, 16214-16225
18. Zhang, M.-T.; Irebo, T.; Johansson, O.; Hammarström, L. J. Am. Chem. Soc. 2011, 133, 13224-13227
19. Reece, S. Y.; Nocera, D. G. J. Am. Chem. Soc. 2005, 127, 9448-9458
20. Costentin, C.; Robert, M.; Savéant, J.-M. J. Am. Chem. Soc. 2006, 128, 8726-8727
21. Costentin, C.; Robert, M.; Savéant, J.-M. J. Am. Chem. Soc. 2007, 129, 9953-9963
22. Correction to ref 7b: Costentin, C.; Robert, M.; Savéant, J.-M. J. Am. Chem. Soc. 2010, 132, 2845
23. Bonin, J.; Costentin, C.; Louault, C.; Robert, M.; Routier, M.; Savéant, J.-M. Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 3367-3372
24. Fecenko, C. J.; Meyer, T. J.; Thorp, H. H. J. Am. Chem. Soc. 2007, 128, 11020
25. Fecenko, C. J.; Thorp, H. H.; Meyer, T. J. J. Am. Chem. Soc. 2007, 128, 15098-15099
26. Westlake, B. C.; Brennaman, M. K.; Concepcion, J. J.; Paul, J. J.; Bettis, S. E.; Hampton, S. D.; Miller, S. A.; Lebedeva, N. V.; Forbes, M. D. E.; Moran, A. M.; Meyer, T. J.; Papanikolas, J. M. Proc. Natl. Acad. Sci. U.S.A. 2011, 108, 8554-8558
27. Moore, G. F.; Hambourger, M.; Gervaldo, M.; Poluektov, O. G.; Rajh, T.; Gust, D.; Moore, T. A.; Moore, A. L. J. Am. Chem. Soc. 2008, 130, 10466
28. Moore, G. F.; Hambourger, M.; Kodis, G.; Michl, W.; Gust, D.; Moore, T. A.; Moore, A. L. J. Phys. Chem. B 2010, 114, 14450
29. Rhile, I. J.; Mayer, J. M. J. Am. Chem. Soc. 2004, 126, 12718-12719
30. 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, 6075-6088
31. Markle, T. F.; Rhile, I. J.; DiPasquale, A. G.; Mayer, J. M. Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 8185-8190
32. Markle, T. F.; Mayer, J. M. Angew. Chem., Int. Ed. 2008, 47, 738-740
33. 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
34. Marcus, R. A.; Sutin, N. Biochim. Biophys. Acta 1985, 811, 265-322
35. Barbara, P. F.; Meyer, J. T.; Ratner, M. A. J. Phys. Chem. 1996, 100, 13148-13168
36. Keifer, P. M.; Hynes, J. T. In Hydrogen-Transfer Reactions; Hynes, J. T.; Klinman, J. P.; Limbach, H.-H.; Schowen, R. L., Eds.; Wiley-VCH: Weinheim, 2006; pp 303-348.
37. Antoniou, D.; Basner, J.; Nunez, S.; Schwartz, S. D. Chem. Rev. 2006, 106, 3170-3187
38. Krishtalik, L. I. Biochim. Biophys. Acta 2000, 1458, 6-27
39. Hammes-Schiffer, S. In Hydrogen-Transfer Reactions; Hynes, J. T.; Klinman, J. P.; Limbach, H. H.; Schowen, R. L., Eds.; Wiley-VCH: Weinheim, 2007; pp 479-503.
40. Hammes-Schiffer, S.; Stuchebrukhov, A. A. Chem. Rev. 2010, 110, 6939-6960
41. Pu, J.; Gao, J.; Truhlar, D. G. Chem. Rev. 2006, 106, 3140-3169
42. Reference 17.
43. Hammes-Schiffer, S. J. Phys. Chem. Lett. 2011, 2, 1410-1416
44. Sirjoosingh, A.; Sharon Hammes-Schiffer, S. J. Phys. Chem. A 2011, 115, 2367-2377 and refs 23-33.
45. Iyengar, S. S.; Sumner, I.; Jakowski, J. J. Phys. Chem. B 2008, 112, 7601-7613
46. Kamerlin, S. C. L.; Warshel, A. J. Phys. Org. Chem. 2010, 23, 677-684
47. Hay, S.; Johannissen, L. O.; Sutcliffe, M. J.; Scrutton, N. S. Biophys. J. 2010, 98, 121-128
48. Boekelheide, N.; Salomón-Ferrer, R.; Miller, T. F., III. Proc. Nat. Acad. Sci. U.S.A. 2011, 108, 16159-16163
49. Clary, D. C. Science 2008, 321, 789-791
50. Iyengar, S. S.; Sumner, S.; Jakowski, J. J. Phys. Chem. B 2008, 112, 7601-7613
51. Siegbahn, P. E. M.; Blomberg, M. R. A. Chem. Rev. 2010, 110, 7040-7061
52. Shaik, S.; Kumar, D.; de Visser, S. P.; Altun, A.; Thiel, W. Chem. Rev. 2005, 105, 2279-2328
53. Derat, E.; Shaik, S. J. Am. Chem. Soc. 2006, 128, 13940-13949
54. DiLabio, G. A.; Ingold, K. U. J. Am. Chem. Soc. 2005, 127, 6693-6699
55. Louwerse, M. J.; Vassilev, P.; Baerends, E. J. J. Phys. Chem. A 2008, 112, 1000-1012
56. Wang, Z.-C.; Xue, W.; Ma, Y.-P.; Ding, X.-L.; He, S.-G.; Dong, F.; Heinbuch, S.; Rocca, J. J.; Bernstein, E. R. J. Phys. Chem. A 2008, 112, 5984-5993
57. A perspective with both adiabatic and non-adiabatic treatments is given in: Tishchenko, O.; Truhlar, D. G.; Ceulemans, A.; Nguyen, M. T. J. Am. Chem. Soc. 2008, 130, 7000-7010
58. el may be quite small, based on the values for the sterically similar self-exchange ET of these reagents: Nelsen, S. F.; Weaver, M. N.; Luo, Y. J. Phys. Chem. A 2006, 110, 11665-11676
59. Soudackov, A.; Hatcher, E.; Hammes-Schiffer, S. J. Chem. Phys. 2005, 122, 014505
60. Hatcher, E.; Soudackov, A. V.; Hammes-Schiffer, S. J. Am. Chem. Soc. 2004, 126, 5763-5775
61. Hatcher, E.; Soudackov, A. V.; Hammes-Schiffer, S. J. Am. Chem. Soc. 2007, 129, 187-196
62. Skone, J. H.; Soudackov, A. V.; Hammes-Schiffer, S. J. Am. Chem. Soc. 2006, 128, 16655-16663
63. Iordanova, N.; Hammes-Schiffer, S. J. Am. Chem. Soc. 2002, 124, 4848-4856
64. Ludlow, M. K.; Soudackov, A. V.; Hammes-Schiffer, S. J. Am. Chem. Soc. 2009, 131, 7094-7102
65. Ludlow, M. K.; Soudackov, A. V.; Hammes-Schiffer, S. J. Am. Chem. Soc. 2010, 132, 1234-1235
66. Iordanova, N.; Decornez, H.; Hammes-Schiffer, S. J. Am. Chem. Soc. 2001, 123, 3723-3733
67. Carra, C.; Iordanova, N.; Hammes-Schiffer, S. J. Am. Chem. Soc. 2003, 125, 10429-10436
68. Ishikita, H.; Soudackov, A. V.; Hammes-Schiffer, S. J. Am. Chem. Soc. 2007, 129, 11146-11152
69. Hazra, A.; Soudackov, A. V.; Hammes-Schiffer, S. J. Phys. Chem. B 2010, 114, 12319-12332
70. Auer, B.; Fernandez, L. E.; Hammes-Schiffer, S. J. Am. Chem. Soc. 2011, 133, 8282-8292
71. The bulk of this study was done concurrently with ref 5e. Markle, T. F. Ph.D. Thesis, University of Washington, 2009.
72. Frisch, M. J.; et al. Gaussian 03, revision D.02; Gaussian, Inc.: Pittsburgh, PA, 2004. See the Supporting Information for a complete citation.
73. Basilevsky, M. V.; Rostov, I. V.; Newton, M. D. Chem. Phys. 1998, 232, 189-199
74. Newton, M. D.; Rostov, I. V.; Basilevsky, M. V. Chem. Phys. 1998, 232, 201-210
75. Basilevsky, M. V.; Chudinov, G. E.; Rostov, I. V.; Liu, Y.-P.; Newton, M. D. J. Mol. Struct. 1996, 371, 191-203
76. Heatwole, E.; Arnaldsson, A.; Prezhdo, O., unpublished work.
77. Newton, T. W. J. Chem. Educ. 1968, 45, 571-575
78. Marcus, R. A. J. Chem. Phys. 1965, 43, 679 (Appendix IV).
79. Marcus, R. A. Faraday Symp. Chem. Soc. 1975, 10, 60
80. For a treatment of the reduced force constant, see: Sutin, N. Prog. Inorg. Chem. 1983, 30, 441-498, especially p 452.
81. Instead of assuming that the proton moves on a surface defined by fixed heavy atoms, the alternative limiting approximation is to assume that all of the nuclear motions occur on the same timescale, which yields adiabatic vibrational surfaces and normal modes (see Supporting Information Figure S1). The differences in these two approaches have been discussed in detail for ortho -hydroxyaryl ketimines: Filarowski, A.; Koll, A.; Hansen, P. E.; Kluba, M. J. Phys. Chem. A 2008, 112, 3478-3485
82. Manner, V. W.; Markle, T. F.; Freudenthal, J. H.; Roth, J. P.; Mayer, J. M. Chem. Commun. 2008, 256-258
83. Using the freq=anharmonic keyword in Gaussian 03, see: Barone, V. J. Chem. Phys. 2005, 122, 014108
84. Bratos, S.; Leicknam, J.-C.; Gallot, G.; Ratajczak, H. In Ultrafast Hydrogen Bonding Dynamics and Proton Transfer Processes in the Condensed Phase; Elsaaesser, T.; Bakker, H. J., Eds.; Kluwer Academic: Boston, 2002; pp 5-30.
85. Fontaine-Vive, F.; Johnson, M. R.; Kearley, G. J.; Howard, J. A. K.; Parker, S. F. J. Am. Chem. Soc. 2006, 128, 2964-2969
86. Jerzierska, A.; Panek, J. J. J. Chem. Theory Comput. 2008, 4, 375-384
87. Klinman, J. P. Biochim. Biophys. Acta 2006, 1757, 981-987
88. Klinman, J. P. Chem. Phys. Lett. 2009, 179-193
89. Liu, B.; Warshel, A. J. Phys. Chem. B 2007, 111, 7852-7861
90. Masgrau, L.; Roujeinikova, A.; Johannissen, L. O.; Hothi, P.; Basran, J.; Ranaghan, K. E.; Mulholland, A. J.; Sutcliffe, M. J.; Scrutton, N. S.; Leys, D. Science 2006, 312, 237
91. Johannissen, L. O.; Hay, S.; Scrutton, N. S.; Sutcliffe, M. J. J. Phys. Chem. B 2007, 111, 2631-2638
92. Hay, S.; Sutcliffe, M. J.; Scrutton, N. S. Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 507
93. Pudney, C. R.; Johannissen, L. O.; Sutcliffe, M. J.; Hay, S.; Scrutton, N. S. J. Am. Chem. Soc. 2010, 132, 11329-11335
94. Peters, B. J. Chem. Theory Comput. 2010, 6, 1447-1454
95. Benkovic, S. J.; Hammes-Schiffer, S. Science 2003, 301, 1196-1202
96. Nagel, Z. D.; Klinman, J. P. Chem. Rev. 2010, 110, PR41-PR67
97. Nelsen, S. F.; Blackstock, S. C.; Kim, Y. J. Am. Chem. Soc. 1987, 109, 677
98. Nelsen, S. F.; Weaver, M. N.; Pladziewicz, J. R.; Ausman, L. K.; Jentzsch, T. L.; O'Konek, J. J. J. Phys. Chem. A 2006, 110, 11665-11676
99. Markle, T. F.; Rhile, I. J.; Mayer, J. M. J. Am. Chem. Soc. 2011, 133, 17341-17352
100. Bell, R. P. The Tunnel Effect in Chemistry; Chapman and Hall: New York, 1980; pp 77-105.