Dioxygen reactivity of biomimetic iron-catecholate and iron-o- aminophenolate complexes of a tris(2-pyridylthio)methanido ligand: Aromatic C-C bond cleavage of catecholate versus o-iminobenzosemiquinonate radical formation

Chemistry - A European Journal

Volumn 18, Issue 37, 2012, Pages 11778-11787

  Halder, Partha ^a   Paria, Sayantan ^a   Paine, Tapan Kanti ^a  

^a DEPARTMENT OF MATERIALS SCIENCE   (India)

Author keywords

biomimetic synthesis; catechols; extradiol cleavage; iron; iron carbon bond

Indexed keywords

ACETONITRILE COMPLEX; BIOMIMETIC SYNTHESIS; BONDING INTERACTIONS; C-C BONDS; CATECHOLATE; CATECHOLS; CLEAVAGE PRODUCTS; DIOXYGEN REACTIVITY; DIOXYGENS; EXTRADIOL; INTERMEDIATE SPECIE; IRON-CARBON BOND; RADICAL COMPLEXES; RADICAL FORMATION; SEMIQUINONE RADICALS;

ACETONITRILE; BIOMIMETICS; CARBON; CHEMICAL BONDS; COMPLEXATION; ELECTROCHEMICAL OXIDATION; IRON; LIGANDS; PHENOLS;

IRON COMPOUNDS;

2 THIOPYRIDINE; 2-THIOPYRIDINE; AMINOPHENOL DERIVATIVE; BENZOQUINONE DERIVATIVE; CATECHOL DERIVATIVE; FERRIC ION; FERROUS ION; LIGAND; OXYGEN; PYRIDINE DERIVATIVE; SEMIQUINONE RADICALS;

ARTICLE; BIOMIMETICS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

AMINOPHENOLS; BENZOQUINONES; BIOMIMETICS; CATECHOLS; FERRIC COMPOUNDS; FERROUS COMPOUNDS; LIGANDS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; OXYGEN; PYRIDINES;

EID: 84865763456     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201200886     Document Type: Article

References (54)

1. G. Jaouen, Bioorganometallics: Biomolecules, Labeling, Medicine, Wiley-VCH, Weinheim, 2006.
2. Metal Ions in Life Sciences Series, Metal-Carbon Bonds in Enzymes and Cofactors, Vol. 6 (Eds.:, A. Sigel, H. Sigel, R. K. O. Sigel,), Royal Society of Chemistry, Cambridge, 2009.
3. D. Mansuy, J. P. Mahy, Metalloporphyrins Catalyzed Oxidations, Kluwer, Dordrecht, 1994.
4. E. J. Corey, S. W. Wright, S. P. T. Matsuda, J. Am. Chem. Soc. 1989, 111, 1452.
5. M. L. Neidig, A. T. Wecksler, G. Schenk, T. R. Holman, E. I. Solomon, J. Am. Chem. Soc. 2007, 129, 7531.
6. S. Shima, O. Pilak, S. Vogt, M. Schick, M. S. Stagni, W. Meyer-Klaucke, E. Warkentin, R. K. Thauer, U. Ermler, Science 2008, 321, 572.
7. T. Hiromoto, K. Ataka, O. Pilak, S. Vogt, M. S. Stagni, W. Meyer-Klaucke, E. Warkentin, R. K. Thauer, S. Shima, U. Ermler, FEBS Lett. 2009, 583, 585.
8. D. Chen, R. Scopelliti, X. Hu, J. Am. Chem. Soc. 2010, 132, 928.
9. D. Chen, R. Scopelliti, X. Hu, Angew. Chem. 2010, 122, 7674
10. Angew. Chem. Int. Ed. 2010, 49, 7512.
11. C. Tard, C. J. Pickett, Chem. Rev. 2009, 109, 2245.
12. X. Wang, Z. Li, X. Zeng, Q. Luo, D. J. Evans, C. J. Pickett, X. Liu, Chem. Commun. 2008, 3555.
13. B. V. Obrist, D. F. Chen, A. Ahrens, V. Schunemann, R. Scopelliti, X. L. Hu, Inorg. Chem. 2009, 48, 3514.
14. B. Li, T. Liu, C. V. Popescu, A. Bilko, M. Y. Darensbourg, Inorg. Chem. 2009, 48, 11283.
15. A. M. Royer, T. B. Rauchfuss, D. L. Gray, Organometallics 2009, 28, 3618.
16. P. Halder, A. Dey, T. K. Paine, Inorg. Chem. 2009, 48, 11501.
17. P. Halder, T. K. Paine, Inorg. Chem. 2011, 50, 708.
18. M. Costas, M. P. Mehn, M. P. Jensen, L. Que, Jr., Chem. Rev. 2004, 104, 939.
19. E. L. Spence, M. Kawamukai, J. Sanvoisin, H. Braven, T. D. H. Bugg, J. Bacteriol. 1996, 178, 5249.
20. U. Lendenmann, J. C. Spain, J. Bacteriol. 1996, 178, 6227.
21. P. Chaudhuri, C. N. Verani, E. Bill, E. Bothe, T. Weyhermüller, K. Wieghardt, J. Am. Chem. Soc. 2001, 123, 2213.
22. C. G. Pierpont, Coord. Chem. Rev. 2001, 216-217, 99.
23. C. G. Pierpont, Coord. Chem. Rev. 2001, 219-221, 415.
24. C. G. Pierpont, C. W. Lange, Prog. Inorg. Chem. 1994, 41, 381.
25. H. Chun, C. N. Verani, P. Chaudhuri, E. Bothe, E. Bill, T. Weyhermüller, K. Wieghardt, Inorg. Chem. 2001, 40, 4157.
26. A. I. Poddel'sky, V. K. Cherkasov, G. A. Abakumov, Coord. Chem. Rev. 2009, 253, 291.
27. N. Kuwamura, R. Kato, K. I. Kitano, M. Hirotsu, T. Nishioka, H. Hashimoto, I. Kinoshita, Dalton Trans. 2010, 39, 9988.
28. D. D. Cox, L. Que, Jr., J. Am. Chem. Soc. 1988, 110, 8085.
29. H. G. Jang, D. D. Cox, L. Que, Jr., J. Am. Chem. Soc. 1991, 113, 9200.
30. D. D. Cox, S. J. Benkovic, L. M. Bloom, F. C. Bradley, M. J. Nelson, L. Que, Jr., D. E. Wallick, J. Am. Chem. Soc. 1988, 110, 2026.
31. S. Paria, P. Halder, T. K. Paine, Inorg. Chem. 2010, 49, 4518.
32. T. Funabiki, T. Yamazaki, A. Fukui, T. Tanaka, S. Yoshida, Angew. Chem. 1998, 110, 527
33. Angew. Chem. Int. Ed. 1998, 37, 513.
34. A. S. Attia, B. J. Conklin, C. W. Lange, C. G. Pierpont, Inorg. Chem. 1996, 35, 1033.
35. W. O. Koch, V. Schünemann, M. Gerdan, A. X. Trautwein, H.-J. Krüger, Chem. Eur. J. 1998, 4, 1255.
36. D. T. Sawyer, G. J. Schrobilgen, S. J. Sutherland, Inorg. Chem. 1982, 21, 4064.
37. A. S. Attia, S. Bhattacharya, C. G. Pierpont, Inorg. Chem. 1995, 34, 4427.
38. D.-H. Jo, Y.-M. Chiou, L. Que, Jr., Inorg. Chem. 2001, 40, 3181.
39. W. O. Koch, H.-J. Krüger, Angew. Chem. 1995, 107, 2928
40. Angew. Chem. Int. Ed. Engl. 1996, 34, 2671.
41. N. Raffard, R. Carina, A. J. Simaan, J. Sainton, E. Rivière, L. Tchertanov, S. Bourcier, G. Bouchoux, M. Delroisse, F. Banse, J.-J. Girerd, Eur. J. Inorg. Chem. 2001, 2249.
42. R. Mayilmurugan, H. Stoeckli-Evans, M. Palaniandavar, Inorg. Chem. 2008, 47, 6645.
43. C. N. Verani, S. Gallert, E. Bill, T. Weyhermüller, K. Wieghardt, P. Chaudhuri, Chem. Commun. 1999, 1747.
44. H. Chun, T. Weyhermüller, E. Bill, K. Wieghardt, Angew. Chem. 2001, 113, 2552
45. Angew. Chem. Int. Ed. 2001, 40, 2489.
46. K. S. Min, T. Weyhermüller, K. Wieghardt, Dalton Trans. 2003, 1126.
47. S. Mukherjee, T. Weyhermüller, K. Wieghardt, P. Chaudhuri, Dalton Trans. 2003, 3483.
48. H. Chun, E. Bill, E. Bothe, T. Weyhermüller, K. Wieghardt, Inorg. Chem. 2002, 41, 5091.
49. V. D. de Castro, G. M. de Lima, C. A. L. Filgueiras, M. T. P. Gambardella, J. Mol. Struct. 2002, 609, 199.
50. Bruker, Version 2.1-0, Bruker AXS, Inc., Madison, WI, 2006.
51. M. J. T. Frisch et al., Gaussian, Inc., Wallingford CT, 2004.
52. C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785.
53. G. A. Petersson, M. A. Al-Laham, J. Chem. Phys. 1991, 94, 6081.
54. N. M. O'boyel, A. L. Tenderholt, K. M. Langner, J. Comput. Chem. 2008, 29, 839.