Biomimetic oxidation of 3,5-di-tert-butylcatechol by dioxygen via Mn-enhanced base catalysis

Inorganic Chemistry

Volumn 45, Issue 18, 2006, Pages 7480-7487

  Szigyártó, Imola Cs ^a   Simándi, László I ^a   Párkányi, László ^b   Korecz, László ^b   Schlosser, Gitta ^b  

^a CHEMICAL RESEARCH CENTER   (Hungary)

^b INSTITUTE OF EXPERIMENTAL MEDICINE   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

2 BENZOQUINONE; 2-BENZOQUINONE; 3,5 DI TERT BUTYLCATECHOL; 3,5-DI-TERT-BUTYLCATECHOL; BENZOQUINONE DERIVATIVE; CATECHOL DERIVATIVE; LIGAND; MANGANESE; ORGANOMETALLIC COMPOUND; OXYGEN;

ARTICLE; BIOMIMETICS; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; KINETICS; OXIDATION REDUCTION REACTION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

BENZOQUINONES; BIOMIMETICS; CATALYSIS; CATECHOLS; CRYSTALLOGRAPHY, X-RAY; KINETICS; LIGANDS; MANGANESE; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; OXIDATION-REDUCTION; OXYGEN;

EID: 33748795791     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic060618v     Document Type: Article

References (70)

1. Sigel, A.; Sigel, H. Manganese and Its Role in Biological Processes. Metal Ions in Biological Systems; Marcel Dekker: New York, 2000; Vol. 37.
2. (a) Whittaker, J. H. Reference 1; Chapter 18, pp 587-611.
3. (b) Yoder, D. W.; Hwang, J.; Penner-Hahn, J. E. Reference 1; Chapter 16, pp 527-557.
4. (c) Gold, M. H.; Youngs, H. L.; Sollewijn Gelpke, M. D. Reference 1; Chapter 17, pp 559-586.
5. (d) Que, L., Jr.; Reynolds, M. F. Reference 1; Chapter 15, pp 505-525.
6. (e) Hoganson, C. W.; Babcock, G. T. Reference 1; Chapter 19, pp 613-656.
7. (f) Ferreira, K. N.; Iverson, T. M.; Maghlaoui, K.; Barber, J.; Iwata, S. Science 2004, 303, 1831-1838.
8. Pecoraro, V. L.; Hsieh, W.-Y. Reference 1; Chapter 14, pp 429-504.
9. (a) Pecoraro, V. L.; Baldwin, M. J.; Gelasco, A. Chem. Rev. 1994, 94 (3), 807-826.
10. (b) Wu, A. J.; Penner-Hahn, J. E.; Pecoraro, V. L. Chem. Rev. 2004, 104 (2), 903-938.
11. (a) Solomon, E. I.; Sundaram, U. M.; Machonkin, T. E. Chem. Rev. 1996, 96 (7), 2563-2606.
12. (b) Than, R.; Feldmann, A. A.; Krebs, B. Coord. Chem. Rev. 1999, 182, 211-241.
13. (c) Gerdemann, C.; Eicken, C.; Krebs, B. Acc. Chem. Res. 2002, 55 (3), 183-191.
14. (d) Zhang, C. X.; Liang, H.-C.; Humphreys, K. J.; Karlin, K. D. In Advances in Catalytic Activation of Dioxygen by Metal Complexes; Simándi, L. I., Ed.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 2003; pp 79-121.
15. (a) Gentschev, P.; Möller; N.; Krebs, B. Inorg. Chim. Acta 2000, 300, 442-452.
16. (b) Wegner, R.; Gottschaldt, M.; Görls, H.; Jäger, E.-G.; Klemm, D. Chem. - Eur. J. 2001, 7 (10), 2143-2157.
17. (c) Fernandes, C.; Neves, A.; Bortoluzzi, A. J.; Mangrich, A. S.; Rentschler, E.; Szpoganicz, B.; Schwingel, E. Inorg. Chim. Acta 2001, 320, 12-21.
18. (d) Torelli, S.; Belle, C.; Hamman, S.; Pierre, J. L.; Saint-Aman, E. Inorg. Chem. 2002, 41 (15), 3983-3989.
19. (e) Ackermann, J.; Meyer, F.; Kaifer, E.; Pritzkow, H. Chem. - Eur. J. 2002, 8 (1), 247-258.
20. (f) Neves, A.; Rossi, L. M.; Bortoluzzi, A. J.; Szpoganicz, B.; Wiezbicki, C.; Schwingel, E.; Haase, W.; Ostrovsky, S. Inorg. Chem. 2002, 41 (7), 1788-1794.
21. (g) Monzani, E.; Quinti, L.; Perotti, A.; Casella, L.; Gullotti, M.; Randaccio, L.; Geremia, S.; Nardin, G.; Faleschini, P.; Tabbi, G. Inorg. Chem. 1998, 37 (5), 553-562.
22. (h) Granata, A.; Monzani, E.; Casella, L. J. Biol. Inorg. Chem. 2004, 9, 903-913.
23. (i) Selmeczi, K.; Réglier, M.; Giorgi, M.; Speier, G. Coord. Chem. Rev. 2003, 245 (1-2), 191-201.
24. (j) Selmeczi, K.; Réglier, M.; Speier, G.; Peintler, G. React. Kinet. Catal. Lett. 2004, 81 (1), 143-151.
25. (k) Chen, P.; Solomon, E. I. Proc. Natl. Acad. Sci. U.S.A. 2004, 101 (36), 13105-13110.
26. (l) Siegbahn, P. E. M. J. Biol. Inorg. Chem. 2004, 9 (5), 577-590.
27. (m) Koval, I. A.; Huisman, M.; Stassen, A. F.; Gamez, P.; Roubeau, O.; Belle, C.; Pierre, J. L.; Saint-Aman, E.; Luken, M.; Krebs, B.; Lutz, M.; Spek, A. L.; Reedijk, J. Eur. J. Inorg. Chem. 2004, 4036-4045.
28. (a) Simándi, T. L.; Simándi, L. I. J. Chem. Soc., Dalton Trans. 1999, 24, 4529-4533.
29. (b) May, Z.; Besenyei, G.; Simándi, L. I.; Asari, D.; Funabiki, T. J. Inorg. Biochem. 2001, 86 (1), 332-332.
30. (c) Simándi, L. I.; Simándi, T. M.; May, Z.; Besenyei, G. Coord. Chem. Rev. 2003, 245 (1-2), 85-93.
31. (d) Simándi, T. M.; May, Z.; Szigyártó, I. C.; Simándi, L. I. Dalton Trans. 2005, 365-368.
32. (a) Krebs, B.; Pursche, D.; Rompel, A.; Triller, M. U.; Hsieh, W. Y.; Pecoraro, V. L. J. Inorg. Biochem. 2003, 96 (1), 172-172.
33. (b) Triller, M. U.; Pursche, D.; Hsieh, W. Y.; Pecoraro, V. L.; Rompel, A.; Krebs, B. Inorg. Chem. 2003, 42 (20), 6274-6283.
34. (c) Paine, T. K.; Weyhermüller, T.; Bothe, E.; Wieghardt, K.; Chaudhuri, P. Dalton Trans. 2003, 3136-3144.
35. (d) Mukherjee, S.; Weyhermüller, T.; Bothe, E.; Wieghardt, K.; Chaudhuri, P. Dalton Trans. 2004, 3842-3853.
36. (a) Simándi, L. I.; Barna, T. M.; Argay, Gy.; Simándi, T. L. Inorg. Chem. 1995, 34 (25), 6337-6340.
37. (b) Simándi, L. L; Simándi, T. L. J. Chem. Soc., Dalton Trans. 1998, 19, 3275-3280.
38. (c) Simándi, L. I. In Advances in Catalytic Activation of Dioxygen by Metal Complexes; Simándi, L. I., Ed.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 2003; pp 265-328.
39. (a) Simándi, L. I. Catalytic Activation of Dioxygen by Metal Complexes; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1992; p 396.
40. Simándi, L. I. Advances in Catalytic Activation of Dioxygen by Metal Complexes; Kluwer Academic Publishers: Dordrecht, The Netherlands, 2003.
41. (a) Jones, R. D.; Summerville, D. A.; Basolo, F. J. Am. Chem. Soc. 1978, 100 (14), 4416-4424.
42. (b) Valentine, J. S.; Quinn, A. E. Inorg. Chem. 1976, 15 (8), 1997-1999.
43. Bhula, R.; Gainsford, G. J.; Weatherburn, D. C. J. Am. Chem. Soc. , 1988, 110 (22), 7550-7552.
44. Bossek, U.; Weyhermüller, T.; Wieghardt, K.; Nuber, B. J.; Weiss, J. J. Am. Chem. Soc. 1990, 112 (17), 6387-6388.
45. Lever, A. B. P.; Wilshire, J. P.; Quan, S. K. J. Am. Chem. Soc. 1979, 101 (13), 3668-3669.
46. Chin, D. H.; Sawyer, D. T.; Schaefer, W. P.; Simmons, C. J. Inorg. Chem. 1983, 22 (5), 752-758.
47. Barratt, D. S.; Gott, G. A.; McAuliffe, C. A. J. Chem. Soc., Dalton Trans. 1988, 8, 2065-2070.
48. (a) Kitajima, N.; Komatsuzaki, H.; Hikichi, S.; Osawa, M.; Morooka, Y. J. Am. Chem. Soc. 1994, 116 (25), 11596-11597.
49. (b) Kitajima, N.; Singh, U. P.; Amagai, H.; Osawa, M.; Moro-oka, Y. J. Am. Chem. Soc. 1991, 113 (20), 7757-7758.
50. Frederick, F. C.; Taylor, L. T. Polyhedron 1986, 5 (3), 887-893.
51. Horwitz, C. P.; Winslow, P. J.; Worden, J. T.; Lisek, C. A. Inorg. Chem. 1993, 32 (1), 82-86.
52. Coleman, W. M.; Taylor, L. T. Inorg. Chim. Acta 1978, 30, L291-L293.
53. (a) Dismukes, G. C.; Sheats, J. E.; Smegal, J. A. J. Am. Chem. Soc. 1987, 109 (23), 7202-7203.
54. Perrée-Fauvet, M.; Gaudemer, A.; Bonvoisin, J.; Girerd, J. J.; Boucly-Goester, C.; Boucly, P. Inorg. Chem. 1989, 28 (23), 3533-3538.
55. Fábián, L; Csordás, V. In Advances in Inorganic Chemistry, Van Eldik, R., Hubbard, C. D., Eds.; Academic Press: Amsterdam, The Netherlands, 2003; Vol. 54, Issue 5, pp 395-461.
56. Hitomi, Y.; Ando, A.; Matsui, H.; Ito, T.; Tanaka, T.; Ogo, S.; Funabiki, T. Inorg. Chem. 2005, 44, 3473-3478.
57. Singh, S.; Chakravortty, V.; Dash, K. C. Indian J. Chem., Sect. A: Inorg., Phys., Theor. Anal. 1989, 28 (3), 255-257.
58. North, A. C. T.; Philips, D. C; Mathews, F. S. Acta Crystallogr. 1968, A24, 351-359.
59. Sheldrick, G. M. SHELXS-97, Program for Crystal Structure Solution; University of Göttingen: Göttingen, Germany, 1997.
60. International Tables for X-ray Crystallography; Wilson, A. J. C., Ed.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1992; Vol. C; Tables 6.1.1.4 (pp 500-502), 4.2.6.8 (pp 219-222), and 4.2.4.2 (pp 193-199).
61. Spek, A. L. Acta Crystallogr. 1990, A46, C-34 (Table A. Crystal data and structure refinement).
62. Grinstead, R. R. Biochemistry 1964, 3, 1308-1314.
63. White, L. S.; Hellman, E. J.; Que, L., Jr. J. Org. Chem. 1982, 47, 3766-3769.
64. (a) Stability Constants of Metal-ion Complexes; Compiled by A. E. Martell; Special Publication No. 17, Section II, Organic Ligands; The Chemical Society: London, 1964; p 489.
65. (b) Brzezinski, B.; Grech, E.; Malarski, Z.; Sobczyk, L. J. Chem. Soc., Perkin Trans. 2 1991, 6, 857-859.
66. Buchanan, R. M.; Fitzgerald, B. J.; Pierpont, C. G. Inorg. Chem. 1979, 18 (12), 3439-3444.
67. (a) Denisov, E. T. The oxidation of alcohols, ketones, ethers, esters and acids in solution. In Liquid-Phase Oxidation, Comprehensive Chemical Kinetics; Bamford, C. H., Tipper, C. F. H., Eds.; Elsevier: Amsterdam, The Netherlands, 1980; Vol. 16.
68. (b) Simándi, L. I. Catalytic Activation of Dioxygen by Metal Complexes; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1992; pp 257-259.
69. Simándi, T. M.; Simándi, L. I.; Gyõr, M.; Rockenbauer, A.; Gömöry, Á. Dalton Trans. 2004, 7, 1056-1060.
70. More O'Ferrall, R. A. J. Chem. Soc. B 1970, 785-790.