Theoretical studies on high-valent manganese porphyrins: Toward a deeper understanding of the energetics, electron distributions, and structural features of the reactive intermediates of enzymatic and synthetic manganese-catalyzed oxidative processes

Israel Journal of Chemistry

Volumn 40, Issue 1, 2000, Pages 1-8

  Ghosh, Abhik ^a   Gonzalez, Emmanuel ^a  

^a UNIVERSITY OF TROMSØ   (Norway)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0034555507     PISSN: 00212148     EISSN: None     Source Type: Journal    
DOI: 10.1560/2YQB-Q2BR-UK2L-AADJ     Document Type: Article

References (58)

1. (a) Sono, M.; Roach, P.; Coulter, E.D.; Dawson, J.H. Chem. Rev. 1996, 96, 2841.
2. (b) Dolphin, D. In Metalloporphyrins Catalyzed Oxidations; Montanari, F.; Casella, L., Eds.; Kluwer Academic: Dordrecht, Netherlands, 1994; p 269.
3. (a) Meunier, B. In Metalloporphyrins Catalyzed Oxidations; Montanari, F.; Casella, L., Eds.; Kluwer Academic; Dordrecht, Netherlands, 1994; p 1.
4. (b) Shilov, A.E.; Karasevich, E.I. In Metalloporphyrins Catalyzed Oxidations; Montanari, F.; Casella, L., Eds.; Kluwer Academic: Dordrecht, Netherlands, 1994; p 87.
5. Mlodnicka, T.; James, B.R. In Metalloporphyrins Catalyzed Oxidations; Montanari, F.; Casella, L., Eds.; Kluwer Academic: Dordrecht, Netherlands, 1994; p 121.
6. Casella, L.; Colonna, S. In Metalloporphyrins Catalyzed Oxidations; Montanari, F.; Casella, L., Eds.; Kluwer Academic: Dordrecht, Netherlands, 1994; p 307.
7. (e) Sheldon, R.A., Ed.; Metalloporphyrins in Catalytic Oxidations; Marcel Dekker: New York, 1994; pp 1-390.
8. (f) Bernadou, J; Meunier, B. Chem. Commun. 1998, 2167.
9. Labat, G.; Seris, J.L.; Meunier B. Angew. Chem., Int. Ed. Engl. 1990, 29, 1471.
10. (b) Dolphin, D; Traylor, T.G.; Xie, L. Y. Acc. Chem. Res. 1997, 30, 251.
11. (a) Meunier, B. Chem. Rev. 1992, 92, 1411.
12. (b) Bigey, P.; Sonnichsen, S.H.; Meunier, B.; Nielsen, P.E. Bioconjugate Chem. 1997, 8, 267.
13. Pitie, M.; Meunier, B. J. Biol. Inorg. Chem. 1996, 1, 239.
14. Song. R; Witvrouw, M; Schols, D; Robert, A; Balzarini, J; DeClercq, E; Bernadou, J; Meunier, B. Antiviral Chem. Chemother. 1997, 8, 85.
15. (a) Cui, F.; Dolphin, D. Can. J. Chem. 1995, 73, 2153.
16. (b) Cui, F.T.; Wijesekera, T.; Dolphin, D.; Farrell, R.; Skerker, P. J. Biotechnol. 1993, 30, 15.
17. (a) Mansuy, D.; Mahy, J.P. In Metalloporphyrins Catalyzed Oxidations; Montanari, F.; Casella, L., Eds,; Kluwer Academic: Dordrecht, Netherlands, 1994; p 175.
18. (b) Du Bois, J.; Tomooka, C.S.; Hong, J.; Carreira, E.M. Acc. Chem. Res. 1997, 30, 364.
19. (a) Yamamoto, S.; Teraoka, J.; Kashiwagi, H. J. Chem. Phys. 1988, 88, 303.
20. (b) Yamamoto, S.; Kashiwagi, H. Chem. Phys. Lett. 1988, 145, 111.
21. Ghosh, A.; Almlöf, J.; Que, L., Jr. J. Phys. Chem. 1994, 98, 5576.
22. Kuramochi, H.; Noodleman, L.; Case, D.A. J. Am. Chem. Soc. 1997, 119, 11442.
23. (e) Ghosh, A.; Almlöf, J.; Que, L., Jr. Angew. Chem., Int. Ed. Engl. 1996, 35, 770.
24. (f) Ghosh, A.; Skancke, A. J. Phys. Chem. B 1998, 102, 10087.
25. Turner, P.; Gunter, M.J. Inorg. Chem. 1994, 33, 1406.
26. Czernuszewicz, R.S.; Su, Y.S.; Stern, M.K.; Macor, K.A.; Kim, D.; Groves, J.T.; Spiro, T.G. J. Am. Chem. Soc. 1988, 110, 4158.
27. (a) Hill, C.H.; Schardt, B.C. J. Am. Chem. Soc. 1980, 102, 8628.
28. (b) Groves, J.T.; Stern, M.K. J. Am. Chem. Soc. 1988, 110, 8628.
29. Balahura, R.J.; Sorokin, A.; Bernadou, J.; Meunier, B. Inorg. Chem. 1997, 36, 3488.
30. Kaustov, L.; Tal, M.E.; Shames, A.I.; Gross, Z. Inorg. Chem. 1997, 36, 3503.
31. For a review of density functional calculations on porphyrins, see; Ghosh, A. Acc. Chem. Res. 1998, 31, 189.
32. The ADF program is obtainable from: Scientific Computing and Modelling, Department of Theoretical Chemistry, Vrije Universiteit, 1081 HV Amsterdam, The Netherlands.
33. Maliyackel, A.C.; Otvos, J.W.; Calvin, M.; Spreer, L.O. Inorg. Chem. 1987, 26, 4133.
34. Camenzind, M.J.; Hollander, F.J.; Hill, C.L. Inorg. Chem. 1983, 22, 3776.
35. Camenzind, M.J.; Hollander, F.J.; Hill, C.L. Inorg. Chem. 1982, 21, 4301.
36. Schappacher, M.; Weiss, R. Inorg. Chem. 1987, 26, 1190.
37. Arasasingham, R.D.; Bruice, T.C. Inorg. Chem. 1990, 29, 1422.
38. Linde, C.; Åkermark, B.; Norrby, P.-O.; Svensson, M. J. Am. Chem. Soc. 1999, 121, 5083.
39. Jin, N.; Groves, J.T. J. Am. Chem. Soc. 1999, 121, 2923.
40. The small negative spin populations in Table 2 refer to the minority spin in our spin-unrestricted calculations and are not of any particular chemical significance.
41. Ghosh, A.; Gonzalez, E.; Vangberg, T. J. Porphyrins Phthalocyanines, in press.
42. Ghosh, A.; Gonzalez, E.; Vangberg, T. J. Phys. Chem. B 1999, 103, 1363.
43. Ghosh, A.; Wondimagegn, T. Unpublished results.
44. Vangberg, T.; Ghosh, A. J. Am. Chem. Soc. 1998, 120, 6227.
45. (a) Safo, M.K.; Walker, F.A.; Raitsimring, A.M.; Walters, W.P.; Dolata, D.P.; Debrunner, P.G.; Scheidt, W.R. J. Am. Chem. Soc. 1994, 116, 7760.
46. (b) Walker, F.A.; Nasri, H.; Turowska-Tyrk, I.; Mohanrao, K.; Watson, C.T.; Shokhirev, N.V.; Debrunner, P.G.; Scheidt, W.R. J. Am. Chem. Soc. 1996, 118, 12109.
47. Ayougou, K.; Bill, E.; Charnock, J.M.; Garner, C.D.; Mandon, D.; Trautwein, A.X.; Weiss, R.; Winkler, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 343.
48. (a) Hashimoto, J.; Tatsuno, Y.; Kitagawa, T. In Proceedings of the Tenth International Conference on Raman Spectroscopy, Peticolas, W.L., Hudson, B., Eds.; University of Oregon, Eugene, OR; pp 1-29.
49. (b) Kitagawa, T.; Mizutani, Y. Coord. Chem. Rev. 1994, 135, 685.
50. Hashimoto, J.; Tatsuno, Y.; Kitagawa, T. Proc. Natl. Acad. Sci. U.S.A. 1986, 83, 2417.
51. Makino, R.; Uno, T.; Nishimura, Y.; Iizuka, T.; Tsuboi, M.; Ishimura, Y. J. Biol. Chem. 1986, 261, 8376.
52. Ghosh, A.; Skancke, A. Unpublished results.
53. Collins, T.J.; Gordon-Wylie, S.W. J. Am. Chem. Soc. 1989, 111, 4511.
54. (b) Collins, T.J.; Powell, R.D.; Slebodnick, C.; Uffelman, E.S. J. Am. Chem. Soc. 1990, 112, 899.
55. MacDonnell, F.M.; Fackler, N.L.P.; Stern, C.; O'Halloran, T.V. J. Am. Chem. Soc. 1994, 116, 7431.
56. (a) Buchler, J.W.; Dreher, C.; Lay, K.-L.; Lee, Y.J.A.; Scheidt, W.R. Inorg. Chem. 1983, 22, 888.
57. (b) Du Bois, J.; Tomooka, C.S.; Hong, J.; Carreira, E.M.; Day, M.W. Angew. Chem., Int. Ed. Engl. 1997, 36, 1645 and references therein.
58. Jepsen, A.S.; Roberson, M.; Hazell, R.G.; Joørgensen, K.A. Chem. Commun. 1998, 1599.