Stepwise protonation and electron-transfer reduction of a primary copper-dioxygen adduct

Journal of the American Chemical Society

Volumn 135, Issue 44, 2013, Pages 16454-16467

  Peterson, Ryan L ^a   Ginsbach, Jake W ^b   Cowley, Ryan E ^b   Qayyum, Munzarin F ^b   Himes, Richard A ^a   Siegler, Maxime A ^a   Moore, Cathy D ^a   Hedman, Britt ^c   Hodgson, Keith O ^b,c   Fukuzumi, Shunichi ^d   Solomon, Edward I ^b   Karlin, Kenneth D ^a  

^a JOHNS HOPKINS UNIVERSITY   (United States)

^b STANFORD UNIVERSITY   (United States)

^c SLAC NATIONAL ACCELERATOR LABORATORY   (United States)

^d OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2-METHYLTETRAHYDROFURAN; DECAMETHYLFERROCENE; ELECTRON-TRANSFER; ELECTRONIC CONFIGURATION; FERROCENIUM SALT; NUCLEAR MAGNETIC RESONANCE(NMR); SECOND-ORDER RATE CONSTANTS; SUPEROXO COMPLEX;

DENSITY FUNCTIONAL THEORY; HYDROGEN BONDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTONATION; RATE CONSTANTS;

FLUORINE;

COPPER; COPPER ION; LIGAND; OXYGEN; PROTON; TRIFLUOROACETIC ACID;

ARTICLE; CRYSTAL STRUCTURE; DECOMPOSITION; DENSITY FUNCTIONAL THEORY; ELECTRON SPIN RESONANCE; ELECTRON TRANSPORT; FLUORINE NUCLEAR MAGNETIC RESONANCE; HYDROGEN BOND; HYDROXYLATION; ISOMERIZATION; KINETICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; OXIDATION REDUCTION POTENTIAL; PROTON TRANSPORT; RAMAN SPECTROMETRY; REACTION ANALYSIS; STATIC ELECTRICITY; STOICHIOMETRY; ULTRAVIOLET SPECTROSCOPY; X RAY ABSORPTION SPECTROSCOPY;

COPPER; CRYSTALLOGRAPHY, X-RAY; ELECTRON TRANSPORT; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; OXIDATION-REDUCTION; OXYGEN; PROTONS; QUANTUM THEORY;

EID: 84887718844     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja4065377     Document Type: Article

References (93)

1. Vielstch, W.; Lamm, A.; Gasteiger, H. A. Handbook of Fuel Cells: Fundamentals, Technology and Applications; Wiley: Hoboken, NJ, 2003.
2. Marković, N. M.; Schmidt, T. J.; Stamenković, V.; Ross, P. N. Fuel Cells 2001, 1, 105-116
3. Cracknell, J. A.; Vincent, K. A.; Armstrong, F. A. Chem. Rev. 2008, 108, 2439-2461
4. Gewirth, A. A.; Thorum, M. S. Inorg. Chem. 2010, 49, 3557-3566
5. Thorseth, M. A.; Tornow, C. E.; Tse, E. C. M.; Gewirth, A. A. Coord. Chem. Rev. 2013, 257, 130-139
6. Fukuzumi, S.; Yamada, Y.; Karlin, K. D. Electrochim. Acta 2012, 82, 493-511
7. Solomon, E. I.; Kjaergaard, C. H.; Heppner, D. E. Molecular Properties and Reaction Mechanism in Multicopper Oxidases Related to Their Use in Biofuel Cell. In Electrochemical Processes in Biological Systems; John Wiley and Sons: Hoboken, NJ; in press.
8. Sono, M.; Roach, M. P.; Coulter, E. D.; Dawson, J. H. Chem. Rev. 1996, 96, 2841-2887
9. Ortiz de Montellano, P. R. Cytochrome P-450: Structure, Mechanism and Biochemistry, 3 rd ed.; Kluwer Academic/Plenum Publishers: New York, 2005.
10. Sheldon, R. A.; Kochi, J. K. Metal-Catalyzed Oxidations of Organic Compounds; Academic Press: New York, 1981.
11. Metal Ion Activation of Dioxygen: Metal Ions in Biology; Spiro, T. G., Ed.; Wiley-Interscience: New York, 1981; Vol. 3.
12. Sheldon, R. A. History of Oxygen Activation 1773-1993. In The Activation of Dioxygen and Homogeneous Catalytic Oxidation; Barton, D. H. R.; Martell, A. E.; Sawyer, D. T., Eds.; Plenum Press: New York, 1993; pp 9-30.
13. Lee, D.; Lippard, S. J. Nonheme Di-Iron Enzymes. In Bio-Coordination Chemistry; Que, L., Jr.; Tolman, W. B., Eds.; Elsevier Ltd.: Oxford, U.K., 2004; Vol. 8; pp 309-342.
14. Costas, M.; Mehn, M. P.; Jensen, M. P.; Que, L. Chem. Rev. 2004, 104, 939-986
15. Solomon, E. I.; Sundaram, U. M.; Machonkin, T. E. Chem. Rev. 1996, 96, 2563-2605
16. Solomon, E. I.; Ginsbach, J. W.; Heppner, D. E.; Kieber-Emmons, M. T.; Kjaergaard, C. H.; Smeets, P. J.; Tian, L.; Woertink, J. S. Faraday Discuss. 2011, 148, 11-39
17. Copper Proteins: Metal Ions in Biology; Spiro, T. G., Ed.; Wiley-Interscience: New York, 1981; Vol. 3.
18. Bioinorganic Chemistry of Copper; Karlin, K. D.; Tyeklár, Z., Eds.; Chapman & Hall: New York, 1993.
19. Copper-Oxygen Chemistry; Itoh, S.; Karlin, K. D., Eds.; John Wiley & Sons, Inc.: Hoboken, NJ, 2011.
20. Klinman, J. P. Chem. Rev. 1996, 96, 2541-2561
21. Klinman, J. P. J. Biol. Chem. 2006, 281, 3013-3016
22. Prigge, S. T.; Eipper, B.; Mains, R.; Amzel, L. M. Science 2004, 304, 864-867
23. Babcock, G. T.; Wikström, M. Nature 1992, 356, 301-309
24. Ferguson-Miller, S.; Babcock, G. T. Chem. Rev. 1996, 96, 2889-2908
25. Wilmot, C. M.; Hajdu, J.; McPherson, M. J.; Knowles, P. F.; Phillips, S. E. V. Science 1999, 286, 1724-1728
26. Metz, M.; Solomon, E. I. J. Am. Chem. Soc. 2001, 123, 4398-4950
27. Solomon, E. I.; Augustine, A. J.; Yoon, J. Dalton Trans. 2008, 3921-3932
28. Humphreys, K. J.; Mirica, L. M.; Wang, Y.; Klinman, J. P. J. Am. Chem. Soc. 2009, 131, 4657-4663
29. Liu, Y.; Mukherjee, A.; Nahumi, N.; Ozbil, M.; Brown, D.; Angeles-Boza, A. M.; Dooley, D. M.; Prabhakar, R.; Roth, J. P. J. Phys. Chem. B 2012, 117, 218-229
30. Chen, P.; Solomon, E. I. J. Am. Chem. Soc. 2004, 126, 4991-5000
31. Bauman, A. T.; Yukl, E. T.; Alkevich, K.; McCormack, A. L.; Blackburn, N. J. J. Biol. Chem. 2006, 281, 4190-4198
32. Chen, P.; Solomon, E. I. Proc. Nat. Acad. Sci. U.S.A. 2004, 101, 13105-13110
33. Crespo, A.; Marti, M. A.; Roitberg, A. E.; Amzel, L. M.; Estrin, D. A. J. Am. Chem. Soc. 2006, 128, 12817-12828
34. Yoshizawa, K.; Kihara, N.; Kamachi, T.; Shiota, Y. Inorg. Chem. 2006, 45, 3034-3041
35. McIntyre, N. R.; Lowe, E. W.; Merkler, D. J. J. Am. Chem. Soc. 2009, 131, 10308-10319
36. Quinlan, R. J.; Sweeney, M. D.; Lo Leggio, L.; Otten, H.; Poulsen, J.-C. N.; Johansen, K. S.; Krogh, K. B. R. M.; Jørgensen, C. I.; Tovborg, M.; Anthonsen, A.; Tryfona, T.; Walter, C. P.; Dupree, P.; Xu, F.; Davies, G. J.; Walton, P. H. Proc. Nat. Acad. Sci. U.S.A. 2011, 108, 15079-15084
37. Phillips, C. M.; Beeson, W. T.; Cate, J. H.; Marletta, M. A. ACS Chem. Biol. 2011, 6, 1399-1406
38. Beeson, W. T.; Phillips, C. M.; Cate, J. H. D.; Marletta, M. A. J. Am. Chem. Soc. 2012, 134, 890-892
39. Li, X.; Beeson, W. T., IV; Phillips, C. M.; Marletta, M. A.; Cate, J. H. D. Structure 2012, 20, 1051-1061
40. Hemsworth, G. R.; Taylor, E. J.; Kim, R. Q.; Gregory, R. C.; Lewis, S. J.; Turkenburg, J. P.; Parkin, A.; Davies, G. J.; Walton, P. H. J. Am. Chem. Soc. 2013, 135, 6069-6077
41. Lewis, E. A.; Tolman, W. B. Chem. Rev. 2004, 104, 1047-1076
42. Mirica, L. M.; Ottenwaelder, X.; Stack, T. D. P. Chem. Rev. 2004, 104, 1013-1045
43. Quant Hatcher, L.; Karlin, K. D. J. Biol. Inorg. Chem. 2004, 9, 669-683
44. Itoh, S. Curr. Opin. Chem. Biol. 2006, 10, 115-122
45. Fujisawa, K.; Tanaka, M.; Morooka, Y.; Kitajima, N. J. Am. Chem. Soc. 1994, 116, 12079-12080
46. Chen, P.; Root, D. E.; Campochiaro, C.; Fujisawa, K.; Solomon, E. I. J. Am. Chem. Soc. 2003, 125, 466-474
47. Jazdzewski, B. A.; Reynolds, A. M.; Holland, P. L.; Young, V. G.; Kaderli, S.; Zuberbuehler, A. D.; Tolman, W. B. JBIC, J. Biol. Inorg. Chem. 2003, 8, 381-393
48. Donoghue, P. J.; Gupta, A. K.; Boyce, D. W.; Cramer, C. J.; Tolman, W. B. J. Am. Chem. Soc. 2010, 132, 15869-15871
49. Schatz, M.; Raab, V.; Foxon, S. P.; Brehm, G.; Schneider, S.; Reiher, M.; Holthausen, M. C.; Sundermeyer, J.; Schindler, S. Angew. Chem., Int. Ed. 2004, 43, 4360-4363
50. Würtele, C.; Gaoutchenova, E.; Harms, K.; Holthausen, M. C.; Sundermeyer, J.; Schindler, S. Angew. Chem., Int. Ed. 2006, 45, 3867-3869
51. Lanci, M. P.; Smirnov, V. V.; Cramer, C. J.; Gauchenova, E. V.; Sundermeyer, J.; Roth, J. P. J. Am. Chem. Soc. 2007, 129, 14697-14709
52. Kunishita, A.; Kubo, M.; Sugimoto, H.; Ogura, T.; Sato, K.; Takui, T.; Itoh, S. J. Am. Chem. Soc. 2009, 131, 2788-2789
53. Kunishita, A.; Ertem, M. Z.; Okubo, Y.; Tano, T.; Sugimoto, H.; Ohkubo, K.; Fujieda, N.; Fukuzumi, S.; Cramer, C. J.; Itoh, S. Inorg. Chem. 2012, 51, 9465-9480
54. Kobayashi, Y.; Ohkubo, K.; Nomura, T.; Kubo, M.; Fujieda, N.; Sugimoto, H.; Fukuzumi, S.; Goto, K.; Ogura, T.; Itoh, S. Eur. J. Inorg. Chem. 2012, 2012, 4574-4578
55. Maiti, D.; Fry, H. C.; Woertink, J. S.; Vance, M. A.; Solomon, E. I.; Karlin, K. D. J. Am. Chem. Soc. 2007, 129, 264-265
56. Maiti, D.; Lee, D.-H.; Gaoutchenova, K.; Würtele, C.; Holthausen, M. C.; Sarjeant, A. A. N.; Sundermeyer, J.; Schindler, S.; Karlin, K. D. Angew. Chem., Int. Ed. 2008, 47, 82-85
57. Woertink, J. S.; Tian, L.; Maiti, D.; Lucas, H. R.; Himes, R. A.; Karlin, K. D.; Neese, F.; Würtele, C.; Holthausen, M. C.; Bill, E.; Sundermeyer, J.; Schindler, S.; Solomon, E. I. Inorg. Chem. 2010, 49, 9450-9459
58. Peterson, R. L.; Himes, R. A.; Kotani, H.; Suenobu, T.; Tian, L.; Siegler, M. A.; Solomon, E. I.; Fukuzumi, S.; Karlin, K. D. J. Am. Chem. Soc. 2011, 133, 1702-1705
59. Kunishita, A.; Ishimaru, H.; Nakashima, S.; Ogura, T.; Itoh, S. J. Am. Chem. Soc. 2008, 130, 4244-4245
60. Dines, M. B. Inorg. Chem. 1972, 11, 2949-2952
61. LeSuer, R. J.; Buttolph, C.; Geiger, W. E. Anal. Chem. 2004, 76, 6395-6401
62. Li, C.-D.; Mella, S. L.; Sartorelli, A. C. J. Med. Chem. 1981, 24, 1089-1092
63. Tenderholt, A.; Hedman, B.; Hodgson, K. O. PySpline; Stanford Synchrotron Radiation Laboratory: Stanford, CA, 2006.
64. George, G. N. EXAFSPAK; Stanford Synchrotron Radiation Laboratory: Stanford, CA, 2000.
65. Rehr, J. J.; Albers, R. C. Rev Mod Phys 2000, 72, 621-654
66. Frisch, M. J.;. Gaussian 09, revision C.01; Gaussian, Inc.: Wallingford, CT, 2009. For the full reference, see the Supporting Information.
67. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
68. Lee, C. T.; Yang, W. T.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789
69. Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623-11627
70. NIST Computational Chemistry Comparison and Benchmark Database; Johnson, R. D., Ed.; NIST Standard Reference Database Number 101 Release 15b; National Institute of Standards and Technology: Gaithersburg, MD, August 2011; http://cccbdb.nist.gov/.
71. Gorelsky, S. I. SWizard, version 4.2; University of Ottawa: Ottawa, Ontario, Canada, 2013; http://www.sg-chem.net/swizard/.
72. Kieber-Emmons, M. T. Lumo, version 1.0.1; Ephrata, PA, 2012; http://www.kieber-emmons.com/Lumo/.
73. Tenderholt, A. L. QMForge, version 2.1; Stanford University: Stanford, CA, USA.
74. Itoh, S. Chemical Reactivity of Copper Active-Oxygen Complexes. In Copper-Oxygen Chemistry; Itoh, S.; Karlin, K. D., Eds.; John Wiley & Sons, Inc.: Hoboken, NJ, 2011; pp 225-282.
75. Liang, H.-C.; Karlin, K. D.; Dyson, R.; Kaderli, S.; Jung, B.; Zuberbühler, A. D. Inorg. Chem. 2000, 39, 5884-5894
76. Spencer, D. J. E.; Aboelella, N. W.; Reynolds, A. M.; Holland, P. L.; Tolman, W. B. J. Am. Chem. Soc. 2002, 124, 2108-2109
77. Reynolds, A. M.; Gherman, B. F.; Cramer, C. J.; Tolman, W. B. Inorg. Chem. 2005, 44, 6989-6997
78. Aboelella, N. W.; Kryatov, S. V.; Gherman, B. F.; Brennessel, W. W.; Young, V. G.; Sarangi, R.; Rybak-Akimova, E. V.; Hodgson, K. O.; Hedman, B.; Solomon, E. I.; Cramer, C. J.; Tolman, W. B. J. Am. Chem. Soc. 2004, 126, 16896-16911
79. Lee, Y.-M.; Kotani, H.; Suenobu, T.; Nam, W.; Fukuzumi, S. J. Am. Chem. Soc. 2008, 130, 434-435
80. Connelly, N. G.; Geiger, W. E. Chem. Rev. 1996, 96, 877-910
81. Smith, D. W.; Andrews, L. J. Chem. Phys. 1974, 60, 81-85
82. Fry, H. C.; Scaltrito, D. V.; Karlin, K. D.; Meyer, G. J. J. Am. Chem. Soc. 2003, 125, 11866-11871
83. DuBois, J. L.; Mukherjee, P.; Collier, A. M.; Mayer, J. M.; Solomon, E. I.; Hedman, B.; Stack, T. D. P.; Hodgson, K. O. J. Am. Chem. Soc. 1997, 119, 8578-8579
84. Kitajima, N.; Fujisawa, K.; Fujimoto, C.; Moro-oka, Y.; Hashimoto, S.; Kitagawa, T.; Toriumi, K.; Tasumi, K.; Nakamura, A. J. Am. Chem. Soc. 1992, 114, 1277-1291
85. Mahapatra, S.; Halfen, J. A.; Wilkinson, E. C.; Pan, G.; Wang, X.; Young, V. G., Jr.; Cramer, C. J.; Que, J., L.; Tolman, W. B. J. Am. Chem. Soc. 1996, 118, 11555-11574
86. Wada, A.; Harata, M.; Hasegawa, K.; Jitsukawa, K.; Masuda, H.; Mukai, M.; Kitagawa, T.; Einaga, H. Angew. Chem., Int. Ed. 1998, 37, 798-799
87. Yamaguchi, S.; Nagatomo, S.; Kitagawa, T.; Funahashi, Y.; Ozawa, T.; Jitsukawa, K.; Masuda, H. Inorg. Chem. 2003, 42, 6968-6970
88. Li, F.; England, J.; Que, L., Jr. J. Am. Chem. Soc. 2010, 132, 2134-2135
89. III-OOH) complex at -78 C. Hydrogen peroxide could be liberated from this species by the addition of acetic acid or other strong acids. See the following: Nam, E.; Alokolaro, P. E.; Swartz, R. D.; Gleaves, M. C.; Pikul, J.; Kovacs, J. A. Inorg. Chem. 2011, 50, 1592-1602
90. Brunold, T. C.; Solomon, E. I. J. Am. Chem. Soc. 1999, 121, 8288-8295
91. Pavlishchuk, V. V.; Addison, A. W. Inorg. Chim. Acta 2000, 298, 97-102
92. Wallar, B. J.; Lipscomb, J. D. Chem. Rev. 1996, 96, 2625-2658
93. Wade, R. S.; Castro, C. E. Chem. Res. Toxicol. 1996, 9, 1382-1390