Hydrogen atom transfer reactions of imido manganese(V) corroie: One reaction with two mechanistic pathways

Journal of the American Chemical Society

Volumn 129, Issue 37, 2007, Pages 11505-11511

  Zdilla, Michael J ^a   Dexheimer, Jennifer L ^a   Abu Omar, Mahdi M ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BOND DISSOCIATION ENTHALPY (BDE); DIHYDROANTHRACENES; HYDROGEN ATOM TRANSFER REACTIONS; ISOSBESTIC BEHAVIORS;

BENZENE; COMPLEXATION; ENTHALPY; HYDROGEN; RATE CONSTANTS;

MANGANESE COMPOUNDS;

9,10 DIHYDROANTHRACENE; 9,9',10,10' TETRAHYDROBIANTHRACENE; [5,10,15 TRIS(PENTAFLUOROPHENYL)CORROLE]MANGANESE NITRO 4 TOLUENESULFONATE; ANTHRACENE DERIVATIVE; HYDROGEN; MANGANESE DERIVATIVE; TOLUENESULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION KINETICS; ELECTRON SPIN RESONANCE; ELECTRON TRANSPORT; ENTHALPY; OXIDATION; PROTON TRANSPORT; REACTION ANALYSIS;

CATALYSIS; ELECTRON SPIN RESONANCE SPECTROSCOPY; ELECTRONS; HYDROGEN; IMIDES; KINETICS; MANGANESE; ORGANOMETALLIC COMPOUNDS; PORPHYRINS; PROTONS; THERMODYNAMICS;

EID: 35048861485     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja073027s     Document Type: Article

References (62)

1. (a) Mayer, J. Acc. Chem. Res. 1998, 31, 441.
2. (b) Meunier, B.; de Visser, S. P.; Shaik, S. Chem. Rev. 2004, 104, 3947.
3. (a) Partenheimer, W. Catal. Today 1995, 23, 69.
4. (b) Koshino, N.; Saha, B.; Espenson, J. H. J. Org. Chem. 2003, 68, 9364.
5. (c) Saha, B.; Koshino, N.; Espenson, J. H. J. Phys. Chem. A 2004, 108, 425.
6. Groves, J. T.; Han, Y. Z. In Cytochrome P450: Structure Mechanisms and Biochemistry; Ortiz de Monellano, P. R., Ed.; Plenum: New York, 1995; Chapter I, pp 3-48.
7. (a) Lee, K. A.; Nam, W. J. Am. Chem. Soc. 1997, 119, 1916.
8. (b) Primus, J.-L.; Boersma, M. G.; Mandon, D.; Boeren, S.; Veeger, C.; Weiss, R.; Rietjens, I. M. C. M. J. Biol. Inorg. Chem. 1999, 4, 274.
9. (c) Lee, Y. J.; Goh, Y. M.; Han, S.-Y.; Kim, C.; Nam, W. Chem. Lett. 1998, 837.
10. (d) Kamaraj, K.; Bandyopadhyay, D. J. Am. Chem. Soc. 1997, 119, 8099.
11. (e) Pratt, J. M.; Ridd, T. I.; King, L. J. J. Chem. Soc., Chem. Commun. 1995, 2297.
12. (f) Machii, K.; Watanabe, Y.; Morishima, I. J. Am. Chem. Soc. 1995, 117, 6691.
13. (g) Watanabe, Y.; Yamaguchi, K.; Morishima, I.; Takehira, K.; Shimizu, M.; Hayakawa, T.; Orita, H. Inorg. Chem. 1991, 30, 2581.
14. (a) Coon, M. J.; Vaz, A. D. N.; McGinnity, D. F.; Peng, H. M. Drug Metab. Dispos. 1998, 26, 1190.
15. (b) Vaz, A. D. N.; McGinnity, D. F.; Coon, M. J. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 3555.
16. (c) Toy, P. H.; Newcomb, M.; Coon, M. J.; Vaz, A. D. N. J. Am. Chem. Soc. 1998, 120, 9718.
17. (d) Vaz, A. D. N.; Pernecky, S. J.; Raner, G. M.; Coon, M. J. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 4644.
18. (e) Toy, P. H.; Dhanabalasingam, B.; Newcomb, M.; Hanna, I. H.; Hollenberg, P. F. J. Org. Chem. 1997, 62, 9114.
19. (f) Pratt, J. M.; Ridd, T. I.; King, L. J. J. Chem. Soc., Chem. Commun. 1995, 2297.
20. (a) Nam, W.; Lim, M. H.; Moon, S. K.; Kim, C. J. Am. Chem. Soc. 2000, 122, 10805.
21. (b) Collman, J. P.; Zeng, L.; Decréau, R. A. Chem. Commun. 2003, 2974.
22. Song, W. J.; Ryu, Y. O.; Song, R.; Nam, W. J. Biol. Inorg. Chem. 2005, 10, 294.
23. (a) Nam, W.; Choi, S. K.; Lim, M. H.; Rohde, J.-U.; Kim, I.; Kim, J.; Kim, C.; Que, L., Jr. Angew. Chem., Int. Ed. 2003, 42, 109.
24. (b) Collman, J. P.; Chien, A. S.; Eberspacher, T. A.; Brauman, J. I. J. Am. Chem. Soc. 2000, 122, 11098.
25. (c) Nam, W.; Lim, M. H.; Lee, H. J.; Kim, C. J. Am. Chem. Soc. 2000, 122, 6641.
26. Wang, S. H.; Mandimutsira, B. S.; Todd, R.; Ramdhanie, B.; Fox, J. P.; Goldberg, D. P. J. Am. Chem. Soc. 2004, 126, 18.
27. Zdilla, M. J.; Abu-Omar, M. M. J. Am. Chem. Soc. 2006, 128, 16971.
28. (a) Tahmassebi, S. K.; McNeil, W. S.; Mayer, J. M. Organometallics 1997, 16, 5342-5353.
29. (b) Wang, K.; Mayer, J. M. J. Org. Chem. 1997, 62, 4248.
30. (c) Cook, G. K.; Mayer, J. M. J. Am. Chem. Soc. 1995, 117, 7139.
31. (d) Gardner, K. A.; Mayer, J. M. Science 1995, 269, 1849.
32. (e) Cook, G. K.; Mayer, J. M. J. Am. Chem. Soc. 1994, 116, 1855.
33. (f) Cook, G. K.; Mayer, J. M. J. Am. Chem. Soc. 1994, 116, 8859.
34. (g) Conry, R. R.; Mayer, J. M. Organometallics 1993, 12, 3179.
35. (h) Conry, R. R.; Mayer, J. M. Organometallics 1991, 10, 3160.
36. (i) Conry, R. R.; Mayer, J. M. Inorg. Chem. 1990, 29, 4862.
37. 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.
38. Lansky, D. E.; Goldberg, D. P. Inorg. Chem. 2006, 45, 5119.
39. Lucas, R. L.; Powell, D. R.; Borovik, A. S. J. Am. Chem. Soc. 2005, 127, 11596.
40. Eckert, N. A.; Vaddadi, S.; Stoian, S.; Lachicotte, R. J.; Cundari, T. R.; Holland, P. L. Angew. Chem., Int. Ed. 2006, 45, 6868.
41. Kogut, E.; Wiencko, H. L.; Zhang, L.; Cordeau, D. E.; Warren, T. H. J. Am. Chem. Soc. 2005, 127, 11249.
42. (a) Shay, D. T.; Yap, G. P. A.; Zakharov, L. N.; Rheingold, A. L.; Theopold, K. H. Angew. Chem.. Int. Ed. 2005, 44, 1508.
43. (b) Shay, D. T.; Yap, G. P. A.; Zakharov, L. N.; Rheingold, A. L.; Theopold, K. H. Angew. Chem., Int. Ed. 2006, 45, 7870.
44. Cowley, R. E.; Bontchev, R. P.; Sorrell, J.; Sarracino, O.; Feng, Y.; Wang, H.; Smith, J. M. J. Am. Chem. Soc. 2007, 129, 2424.
45. (a) Brown, S. D.; Peters, J. C. J. Am. Chem. Soc. 2004, 126, 4538.
46. (b) Bart, S. C.; Lobkovsky, E.; Bill, Eckhard; Chirik, P. J. J. Am. Chem. Soc. 2006, 128, 5302.
47. Liguori, L.; Bjørsvik, H.-R.; Fontana, F.; Bosco, D.; Galimberti, L; Minisci, F. J. Org. Chem. 1999, 64, 8812.
48. IV signal was never observed.
49. 14 to escape the solvent cage and couple, even in the more viscous dimethylacetamide solvent. The likelihood of benzene solvent cage completely preventing any radical coupling is quite small.
50. 10
51. Camenzind, M. J.; Hollander, F. J.; Hill, C. L. Inorg. Chem. 1983, 22, 3776.
52. Golubkov, G.; Bendix, J.; Gray, H. B.; Mahammed, A.; Goldberg, I.; DiBilio, A. J.; Gross, Z. Angew. Chem.. Int. Ed. 2001, 40, 2132.
53. (a) For phenols with X = OMe, 'Bu, Me, and H, the BDE values as measured by Pedulli were used: Lucarini, M.; Pedrielli, P.; Pedulli, G. F.; Cabiddu, S.; Fattuoni, C. J. Org. Chem. 1996, 61, 9259.
54. (b) For X = CN, Ac the BDE values were approximated using the ABDEs reported by Bordwell: Bordwell, F. G.; Cheng, J.-P. J. Am. Chem. Soc. 1991, 113, 1736. While these BDE values are not exact, 18 cases were examined by Pedulli (reference 26a) and were shown to be highly accurate with one exception for 4-methoxytetramethylphenol, which was attributed to steric reorientation of the oxygen lone pair orbital. These approximations are therefore sufficient to establish BDE trends.
55. Cohen, L. A.; Jones, W. M. J. Am. Chem. Soc. 1963, 81, 3397.
56. Chen, K.; Hirst, J.; Camba, R.; Bonagura, C. A.; Stout, C. D.; Burgess, B. K.; Armstrong, F. A. Nature 2000, 405, 814.
57. (a) Haim, A. Acc. Chem. Res. 1975, 8, 264.
58. (b) Fraser, R. T. M.; Taube, H. J. Am. Chem. Soc. 1961, 83, 2239.
59. Macikenas, D.; Skrzypczak-Jankun, E.; Prostasiewicz, J. D. J. Am. Chem. Soc. 1999, 121, 7164.
60. Mayr, H.; Lang, G.; Ofial, A. R. J. Am. Chem. Soc. 2002, 124, 4076.
61. MacDougall, D. J.; Noll, B. C.; Kennedy, A. R.; Henderson, K. W. Dalton Trans. 2006, 1875.
62. Stoll, S.; Schweiger, A. J. Magn. Reson. 2006, 178, 42.