Activation of C-H/H-H bonds by rhodium(II) porphyrin bimetalloradicals

Journal of the American Chemical Society

Volumn 126, Issue 26, 2004, Pages 8266-8274

  Cui, Weihong ^a   Wayland, Bradford B ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ENERGY; BIMETALS; ENTHALPY; FREE ENERGY; HYDROGEN BONDS; ORGANOMETALLICS; PHASE TRANSITIONS;

BIMETALLORADICALS; REACTIVITY; TERMOLECULAR REACTIONS;

RHODIUM COMPOUNDS;

CARBON; DEUTERIUM; HYDROGEN; ISOTOPE; METAL DERIVATIVE; PORPHYRIN DERIVATIVE; RHODIUM DERIVATIVE;

ARTICLE; CHEMICAL BINDING; ENTHALPY; HYDROGEN BOND; KINETICS; PHASE TRANSITION; REACTION ANALYSIS; THERMODYNAMICS;

EID: 3042729899     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja049291s     Document Type: Article

References (74)

1. Sherry, A. E.; Wayland, B. B. J. Am. Chem. Soc. 1990, 112, 2, 1259.
2. Wayland, B. B.; Ba, S.; Sherry, A. E. J. Am. Chem. Soc. 1991, 113, 3, 5305.
3. Zhang, X.-X.; Wayland, B. B. J. Am. Chem. Soc. 1994, 116, 7897.
4. Cui, W.; Zhang, X. P.; Wayland, B. B. J. Am. Chem. Soc, 2003, 125, 4994.
5. Nelson, A. P.; DiMagno, S. G. J. Am. Chem. Soc. 2000, 122, 8569.
6. (a) Wayland, B. B.; Del Rossi, K. J. J. Organomet. Chem. 1984, 276, C27.
7. (b) Del Rossi, K. J.; Wayland, B. B. J. Am. Chem. Soc. 1985, 107, 7, 7941.
8. Jones, W. D. Top. Organomet. Chem. 1999, 3, 9.
9. (a) Jones, W. D.; Feher, F. J. Acc. Chem. Res. 1989, 22, 2, 91.
10. (b) Jones, W. D.; Feher, F. J. J. Am. Chem. Soc. 1984, 106, 6, 1650.
11. (c) Jones, W. D.; Feher, F. J. J. Am. Chem. Soc. 1986, 108, 16, 4814.
12. (a) Jones, W. D.; Hessell, E. T. J. Am. Chem. Soc. 1992, 114, 15, 6087.
13. (b) Hessell, E. T.; Jones, W. D. Organometallics 1992, 11, 1496.
14. (c) Jones, W. D.; Hessell, E. T. J. Am. Chem. Soc. 1993, 115, 2, 554.
15. (a) Janowicz, A. H.; Bergman, R. G. J. Am. Chem. Soc. 1982, 104, 352.
16. (b) Janowicz, A. H.; Bergman, R. G. J. Am. Chem. Soc. 1983, 105, 12, 3929.
17. (a) Bergman, R. G. Adv. Chem. Ser. 1992, 230, 211.
18. (b) Bergman, R. G. Science 1984, 223, 902.
19. (a) Hoyano, J. K.; Graham, W. A. G. J. Am. Chem. Soc. 1982, 104, 3723.
20. (b) Ghosh, C. K.; Graham, W. A. G. J. Am. Chem. Soc. 1987, 109, 4726.
21. (a) Labinger, J. A.; Bercaw, J. E. Nature 2002, 417, 507.
22. (b) Fekl, U.; Goldberg, K. I. Adv. Inorg. Chem. 2003, 54, 259.
23. (c) Jensen, M. P.; Wick, D. D.; Reinartz, S.; White, P. S.; Templeton, J. L.; Goldberg, K. I. J. Am. Chem. Soc. 2003, 125, 8614.
24. (d) Norris, C. M.; Reinartz, S.; White, P. S.; Templeton, J. L. Organometallics 2002, 21, 5649.
25. (e) Reinartz, S.; White, P. S.; Brookhart, M.; Templeton, J. L. J. Am. Chem. Soc, 2001, 123, 12724.
26. (a) Thompson, M. E.; Bercaw, J. E. Pure Appl. Chem. 1984, 56, 1.
27. (b) Thompson, M. E.; Baxter, S. M.; Bulls, A. R.; Burger, B. J.; Nolan, M. C.; Santarsiero, B. D.; Schaefer, W. P.; Bercaw, J. E. J. Am. Chem. Soc. 1987, 109, 203.
28. Johansson, L.; Tilset, M.; Labinger, J. A.; Bercaw, J. E. J. Am. Chem. Soc. 2000, 122, 10846.
29. (a) Schaller, C. P.; Cummins, C. C.; Wolczanski, P. T. J. Am. Chem. Soc. 1996, 118, 591.
30. (b) Schaller, C. P.; Wolczanski, P. T. Inorg. Chem. 1993, 32, 131.
31. (a) Bennett, J. L.; Wolczanski, P. T. J. Am. Chem. Soc. 1994, 116, 2179.
32. (b) Bennett, J. L.; Wolczanski, P. T. J. Am. Chem. Soc. 1997, 119, 10696.
33. Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879.
34. (a) Aoyama, Y.; Yoshida, T.; Sakurai, K.; Ogoshi, H. J. Chem. Soc., Chem. Commun. 1983, 478.
35. (b) Aoyama, Y.; Yoshida, T.; Sakurai, K.; Ogoshi, H. Organometallics 1986, 5, 168.
36. Wayland, B. B.; Sherry, A. E.; Bunn, A. G. J. Am. Chem. Soc. 1993, 115, 7675.
37. Wayland, B. B.; Ba, S.; Sherry, A. E. Inorg. Chem. 1992, 31, 148.
38. (a) Halpern, J.; Pribanic, M. Inorg. Chem. 1970, 9, 2616.
39. (b) Halpern, J. Inorg. Chim. Acta 1982, 62, 31.
40. (c) Halpern, J. Inorg. Chim. Acta 1983, 77, L105.
41. (a) Capps, K. B.; Bauer, A.; Kiss, G.; Hoff, C. D. J. Organomet. Chem. 1999, 586, 23.
42. (b) Hoff, C. D. Coord. Chem. Rev. 2000, 206-207, 451.
43. Fendrick, C. M.; Marks, T. J. J. Am. Chem. Soc. 1986, 108, 425.
44. Walsh, P. J.; Hollander, F. J.; Bergman, R. G. J. Am. Chem. Soc. 1988, 110, 8729.
45. Jones, W. D. Acc. Chem. Res. 2003, 36, 140.
46. Churchill, D. G.; Janak, K. E.; Wittenberg, J. S.; Parkin, G. J. Am. Chem. Soc. 2003, 125, 1403.
47. Periana, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1986, 108, 7332.
48. Zhang, X.-X.; Parks, G. F.; Wayland, B. B. J. Am. Chem. Soc. 1997, 119, 7938.
49. Zhang, X.-X.; Wayland, B. B. Inorg. Chem. 2000, 39, 5318.
50. Slaughter, L. M.; Wolczanski, P. T.; Klinckman, T. R.; Cundari, T. R. J. Am. Chem. Soc. 2000, 122, 7953.
51. (a) Melander, L.; Saunders, W. H., Jr. Reaction Rates of Isotopic Molecules; Wiley-Interscience: New York, 1980.
52. (b) Lowry, T. H.; Richardson, K. S. Mechanism and Theory in Organic Chemistry, 3rd ed.; Harper & Row: New York, 1987.
53. (c) Carpenter, B. K. Determination of Reaction Mechanisms; Wiley-Interscience: New York, 1984.
54. (d) Isotope Effects in Chemical Reactions; Collins, C. J., Bowman, N. S., Eds.; ACS Monograph No. 167; Van Nostrand Reinhold Co.: New York, 1970.
55. Harper, T. G. P.; Shinomoto, R. S.; Deming, M. A.; Flood, T. C. J. Am. Chem. Soc. 1988, 110, 7915.
56. (a) Bengali, A. A.; Schultz, R. H.; Moore, C. B.; Bergman, R. G. J. Am. Chem. Soc. 1994, 116, 9585.
57. (b) Schultz, R. H.; Bengali, A. A.; Tauber, M. J.; Weiller, B. H.; Wasserman, E. P.; Kyle, K. R.; Moore, C. B.; Bergman, R. G. J. Am. Chem. Soc. 1994, 116, 7369.
58. Buchanan, J. M.; Stryker, J. M.; Bergman, R. G. J. Am. Chem. Soc. 1986, 108, 1537.
59. Bullock, R. M.; Headford, C. E. L.; Hennessy, K. M.; Kegley, S. E.; Norton, J. R. J. Am. Chem. Soc. 1989, 111, 3897.
60. (a) Parkin, G.; Bercaw, J. E. Organometallics 1989, 8, 1172.
61. (b) Stahl, S. S.; Labinger, J. A.; Bereaw, J. E. J. Am. Chem. Soc. 1996, 118, 5961.
62. Gould, G. L.; Heinekey, D. M. J. Am. Chem. Soc. 1989, 111, 5502.
63. Wang, C.; Ziller, J. W.; Flood, T. C. J. Am. Chem. Soc. 1995, 117, 1647.
64. Johnston, H. S. Gas-Phase Reaction Rate Theory: The Ronald Press Co.: New York, 1966; p 239.
65. Chiltz, G.; Eckling, R.; Goldfinger, P.; Huybrechts, G.; Johnston, H. S.; Meyers, L.; Verbeke, G. J. Chem. Phys. 1963, 38, 1053.
66. Wayland, B. B.; Feng, Y.; Ba, S. Organometallics 1989, 8, 1438.
67. Blanksby, S. J.; Ellison, G. B. Acc. Chem. Res. 2003, 36, 255.
68. Wayland, B. B.; Coffin, V. L.; Farnos, M. D. Inorg. Chem. 1988, 27, 2745.
69. Wayland, B. B. Polyhedron 1988, 7, 1545.
70. Stoutland, P. O.; Bergman, R. G.; Nolan, S. P.; Hoff, C. D. Polyhedron 1988, 7, 1429.
71. MacKinetics, written by and obtained from Leipold, W. S., III; Weiher, J. F.; McKinney, R. J. E. I. Du pont de Nemours, Inc., 1992-1995.
72. Farnos, M. D. Ph.D. Thesis, University of Pennsylvania, 1986.
73. Evans, F. D.; Battino, R. J. Chem. Thermodyn. 1971, 3, 753.
74. Brunel, R. F.; VanBibber, K. Int. Crit. Tables 1928, 3, 27.