Synthesis and characterization of ruthenium bis(β-diketonato) pyridine-imidazole complexes for hydrogen atom transfer

Inorganic Chemistry

Volumn 46, Issue 26, 2007, Pages 11190-11201

  Wu, Adam ^a   Masland, Joshua ^a   Swartz, Rodney D ^a,b   Kaminsky, Werner ^a,b   Mayer, James M ^a  

^a UNIVERSITY OF WASHINGTON   (United States)

^b UW Chemistry Crystallographic Facility

Author keywords

[No Author keywords available]

Indexed keywords

HYDROGEN; IMIDAZOLE; IMIDAZOLE DERIVATIVE; ORGANOMETALLIC COMPOUND; RUTHENIUM DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SPECTROPHOTOMETRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; HYDROGEN; IMIDAZOLES; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; RUTHENIUM COMPOUNDS; SPECTROPHOTOMETRY;

EID: 38149141010     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic7015726     Document Type: Article

References (94)

1. (a) Cukier, R. I.; Nocera, D. G. Annu. Rev. Phys. Chem. 1998, 49, 337.
2. (b) 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, Germany, 2007; Vol. 2, pp 503-562.
3. (c) Stubbe, J.; Nocera, D. G.; Yee, C. S.; Chang, M. C. Y. Chem. Rev. 2003, 103, 2167.
4. (d) Hammes-Schiffer, S. In Hydrogen-Transfer Reactions; Hynes, J. T., Klinman, J. P., Limbach, H.-H., Schowen, R. L. Eds.; Wiley-VCH: Weinheim, Germany, 2007; Vol. 2, pp 479-502.
5. (e) Meyer, T. J.; Huynh, M. H. V. Inorg. Chem. 2003, 42, 8140.
6. (a) Mayer, J. M. Annu. Rev. Phys. Chem. 2004, 55, 363.
7. (b) Mayer, J. M.; Rhile, I. J. Biochim. Biophys. Acta 2004, 1655, 51.
8. (c) Mayer, J. M.; Rhile, I. J.; Larsen, F. B.; Mader, E. A.; Markle, T. F.; DiPasquale, A. G. Photosynth. Res. 2006, 87, 3.
9. (d) Mayer, J. M.; Mader, E. A.; Roth, J. P.; Bryant, J. R.; Matsuo, T.; Dehestani, A.; Bales, B. C.; Watson, E. J.; Osako, T.; Valliant-Saunders, K.; Lam, W.-H.; Hrovat, D. A.; Borden, W. T.; Davidson, E. R. J. Mol. Catal. A: Chem. 2006, 251, 24.
10. Mayer, J. M. Acc. Chem. Res. 1998, 31, 441.
11. (a) Knapp, M. J.; Meyer, M.; Klinman, J. P. In Hydrogen-Transfer Reactions; Hynes, J. T., Klinman, J. P., Limbach, H.-H., Schowen, R. L., Eds.; Witey-VCH: Weinheim, Germany, 2007; Vol. 4, pp 1241-1284.
12. (b) Knapp, M. J.; Rickert, K.; Klinman, J. P. J. Am. Chem. Soc. 2002, 124, 3865.
13. (c) Glickman, M. H.; Klinman, J. P. Biochemistry 1996, 35, 12882.
14. There are also many examples of HAT-involving metal hydride complexes, for instance: (a) Song, J.-S.; Bullock, R. M.; Creutz, C. J. Am. Chem. Soc. 1991, 113, 9862.
15. (b) Edidin, R. T.; Sullivan, J. M.; Norton, J. R. J. Am. Chem. Soc. 1987, 109, 3945.
16. (a) Roth, J. P.; Lovell, S.; Mayer, J. M. J. Am. Chem. Soc. 2000, 122, 5486.
17. (b) Roth, J. P.; Mayer, J. M. Inorg. Chem. 1999, 38, 2760.
18. (c) Burnett, M. G.; McKee, V.; Nelson, S. M. J. Chem. Soc., Dalton Trans. 1981, 1492.
19. (d) Wang, J. C.; Bauman, J. E., Jr. Inorg. Chem. 1965, 4, 1613.
20. (a) Roth, J. P.; Yoder, J. C.; Won, T.-J.; Mayer, J. M. Science 2001, 294, 2524.
21. (b) Mader, E. A.; Davidson, E. R.; Mayer, J. M. J. Am. Chem. Soc. 2007, 129, 5153.
22. (c) Mader, E. A.; Larsen, A. S.; Mayer, J. M. J. Am. Chem. Soc. 2004, 126, 8066.
23. (d) Yoder, J. C.; Roth, J. P.; Gussenhoven, E. M.; Larsen, A. S.; Mayer, J. M. J. Am. Chem. Soc. 2003, 125, 2629.
24. (a) Wherland, S. Coord. Chem. Rev. 1993, 123, 169.
25. (b) Meyer, T. J.; Taube, H. In Comprehensive Coordination Chemistry; Wilkinson, G. Ed.; Pergamon: New York, 1987; Vol. 1, pp 331-384.
26. (a) Lomoth, R.; Magnuson, A.; Sjödin, M.; Huang, P.; Styring, S.; Hammarström, L. Photosynth. Res. 2006, 87, 25.
27. (b) Sjödin, M.; Styring, S.; Wolpher, H.; Xu, Y.; Sun, L.; Hammarström, L. J. Am. Chem. Soc. 2005, 127, 3855.
28. Cape, J. L.; Bowman, M. K.; Kramer, D. M. J. Am. Chem. Soc. 2005, 127, 4208.
29. (a) Roberts, J. A.; Kirby, J. P.; Nocera, D. G. J. Am. Chem. Soc. 1995, 117, 8051.
30. (b) Kirby, J. P.; Roberts, J. A.; Nocera, D. G. J. Am. Chem. Soc. 1997, 119, 9230.
31. (c) Facenko, C. J.; Meyer, T. J.; Thorp, H. H. J. Am. Chem. Soc. 2006, 128, 11020.
32. Hughey, J. L.; IV;, Knapp, S.; Schugar, H. Synthesis 1980, 6, 489.
33. (a) Haga, M. Inorg. Chim. Acta 1983, 75, 29.
34. (b) Haga, M.; Tsunemitsu, A. Inorg. Chim. Acta 1989, 164, 137.
35. Baird, I. R.; Cameron, B. R.; Skerlj, R. T. Inorg. Chim. Acta 2003, 353, 107.
36. Baird, I. R.; Rettig, S. J.; James, B. R.; Skov, K. A. Can. J. Chem. 1999, 77, 1821.
37. El-Hendawy, A. M.; Alqaradawi, S. Y.; Al-Madfa, H. A. Transition Met. Chem. 2000, 25, 572.
38. Haga, M. Inorg. Chim. Acta 1983, 77, L39.
39. Carter, E.; Kanzelberger, M. A. Unpublished data, 2003.
40. 13a
41. 2(3-amino-6-(3,5-dimethylpyrazol-1- yl)-1,2,4,5-tetrazine): Nayak, A.; Patra, S.; Sarkar, B.; Ghumaan, S.; Puranik, V. G.; Kaim, W.; Lahiri, G. K. Polyhedron, 2005, 24, 333.
42. 4) (L = 2,2′-dipyridylamine): Kar, S.; Chanda, N.; Mobin, S. M.; Urbanos, F. A.; Niemeyer, M.; Puranik, V. G.; Jimenez-Aparicio, R.; Lahiri, G. K. Inorg. Chem. 2005, 44, 1571.
43. 2(N-phenyl-1,2-benzoquinone-diimine): Mitra, K. N.; Choudhury, S.; Castiòeiras, A.; Goswami, S. J. Chem. Soc., Dalton Trans. 1998, 2901.
44. 3: ref 15.
45. 2: Lee, F.-J.; Chi, Y.; Liu, C.-S.; Hsu, P.-F.; Chou, T.-Y.; Peng, S.-M.; Lee, G.-H. Chem. Vap. Deposition 2001, 7, 99 (which reports slightly longer Ru-O distances, 2.050(2)-2.081(2) ̊, compared to those in 4 and 5).
46. 2: Colson, S. F.; Robinson, S. D.: Robinson, P. D.; Hinckley, C. C. Acta Crystallogr. C 1989, 45, 715.
47. (a) Tadokoro, M.; Kanno, H.; Kitajima, T.; Shimada-Umemoto, H.; Nakanishi, N.; Isobe, K.; Nakasuji, K. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 4950.
48. (b) Mandon, D.; Ott-Woelfel, F.; Fischer, J.; Weiss, R.; Bill, E.; Trautwein, A. X. Inorg. Chem. 1990, 29, 2442.
49. (c) Mayboroda, A.; Comba. P.; Pritzkow, H.; Rheinwald, G.; Lang, H.; van Koten, G. Eur. J. Inorg. Chem. 2003, 1703.
50. Jeffrey, G. A. An Introduction to Hydrogen Bonding; Oxford University Press: New York, 1997.
51. Walstrom, A.; Pink, M.; Tsvetkov, N. P.; Fan, H.; Ingleson, M.; Caulton, K. G. J. Am. Chem. Soc. 2005, 127, 16780: supporting information.
52. 3.
53. (a) Kennedy, D. C.; Wu, A.; Patrick, B. O.; James, B. R. Inorg. Chem. 2005, 44, 6529.
54. (b) Belle, C.; Bougault, C.; Averbuch, M.-T., Durif, A.; Pierre, J.-L.; Latour, J.-M. Le Pape, L. J. Am. Chem. Soc. 2001, 123, 8053.
55. (c) Bertini, I.; Capozzi, F.; Luchinat, C.; Turano, P. J. Magn. Reson. 1991, 95, 244.
56. Izutsu, K. Acid-Base Dissociation Constants in Dipolar Aprotic Solvents; Blackwell Scientific: Boston, 1990.
57. Schwesinger, R.; Schlemper, H. Angew. Chem., Int. Ed. Engl. 1987, 26, 1167.
58. Wu, A.; Mayer, J. M., to be submitted.
59. Ghumaan, S.; Sarkar, B.; Patra, S.; Parimal, K.; van Slageren, J.; Fiedler, J.; Kaim, W.; Lahiri, G. K. J. Chem. Soc., Dalton Trans. 2005, 706.
60. Seddon, E. A.; Seddon, K. R. The Chemistry of Ruthenium; Elsevier: Amsterdam, The Netherlands, 1984; p 474.
61. Ref 7c: supporting information.
62. (a) Bandlish, B. K.; Shine, H. J. J. Org. Chem. 1977, 42, 561.
63. (b) Eberson, L.; Larsson, B. Acta Chem. Scand., Ser. B 1986, 40, 210.
64. (c) 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 and references therein.
65. Gould, I. R.; Ege, D.; Moser, J. E.; Farid, S. J. Am. Chem. Soc. 1990, 112, 4290.
66. Mohammadpoor-Baltork, I.; Abdollahi-Alibeik, M. Bull. Korean Chem. Soc. 2003, 24, 1354.
67. Keene, F. R. Coord. Chem. Rev. 1999, 187, 121 and references therein.
68. (a) Tilset, M. In Electron Transfer in Chemistry; Balzani, V., Ed.; Wiley-VCH: Weinheim, Germany, 2001; Vol. 2, pp 677-713.
69. (b) Parker, V. D.; Handoo, K. L.; Roness, F.; Tilset, M. J. Am. Chem. Soc. 1991, 113, 7493.
70. 2 in MeCN.
71. Kolthoff, I. M.; Chantooni, M. K., Jr. J. Phys. Chem. 1972, 76, 2024.
72. CRC Handbook of Chemistry and Physics, 67th ed.; Weast, R. C., Ed.; CRC Press: Boca Raton, FL, 1986-1987; p D-69.
73. Brunner, E. J. Chem. Eng. Data 1985, 30, 269.
74. 37
75. G cancels itself out.
76. Gas-phase thermochemical data from NIST Chemistry Webbook, June 2005 release.
77. This analysis follows that in Soper, J. D.; Rhile, I. J.; DiPasquale, A. G.; Mayer, J. M. Polyhedron 2004, 23, 323 and references therein.
78. -1 in MeOH: Goldsmith, C. R.; Jonas, R. T.; Stack, T. D. P. J. Am. Chem. Soc. 2002, 124, 83.
79. -1 in MeCN: Goldsmith, C. R.; Cole, A. P.; Stack, T. D. P. J. Am. Chem. Soc. 2005, 127, 9904.
80. -1, were not isolated.): Gupta, R.; Borovik, A. S. J. Am. Chem. Soc. 2003, 125, 13234.
81. -1 in MeCN: ref. 1e and Bryant, J. R.; Mayer, J. M. J. Am. Chem. Soc. 2003, 125, 10351.
82. -1 in MeCN: ref. 3.
83. 2: Qin, K.; Incarvito, C. D.; Rheingold, A. L.; Theopold, K. H. J. Am. Chem. Soc. 2002, 124, 14008.
84. -1) in MeCN: Kaizer, J.; Klinker, E. J.; Oh, N. Y.; Rohde, J.-U.; Song, W. J.; Stubna, A.; Kim, J.; Münck, E.; Nam, W.; Que, L., Jr.
85. -1 in DMSO: Bordwell, F. G.; Liu, W. Z. J. Am. Chem. Soc. 1996, 118, 10819.
86. 1/2 = 1.22 V).
87. Lever, A. B. P. Inorg. Chem. 1990, 29, 1271.
88. Pratt, D. A.; DiLabio, G. A.; Mulder, P.; Ingold, K. U. Acc. Chem. Res. 2004, 37, 334.
89. (a) Raebiger, J. W.; Miedaner, A.; Curtis, C. J.; Miller, S. M.; Anderson, O. P.; DuBois, D. L. J. Am. Chem. Soc. 2004, 126, 5502.
90. (b) Fraze, K.; Wilson, A. D.; Appel, A. M.; Rakowski, DuBois, M.; DuBois, D. L. Organometallics 2007, 26, 3918-3924.
91. Armarego, W. L. F.; Chai, C. L. L. Purification of Laboratory Chemicals 5th Ed.; Butterworth-Heinemann: Amsterdam, The Netherlands, 2003.
92. Otwinowski, Z.; Minor, W. In Methods in Enzymology; Carter, C. W., Jr., Sweet, R. M., Eds.; Academic Press: New York, 1997; Vol. 276, pp 307-326.
93. Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A.; Burla, M. C.; Polidori, G.; Camalli, M. J. Appl. Crystallogr. 1994, 27, 435.
94. Sheldrick, G. M. SHELXL-97: Program for the Refinement of Crystal Structures; University of Göttingen: Göttingen, Germany, 1997.