Oxidation of polycyclic aromatic hydrocarbons catalyzed by iron tetrasulfophthalocyanine FePcS: Inverse isotope effects and oxygen labeling studies

European Journal of Inorganic Chemistry

Volumn , Issue 9, 1998, Pages 1269-1281

  Sorokin, Alexander ^a   Meunier, Bernard ^a  

^a LCC LABORATOIRE DE CHIMIE DE COORDINATION   (France)

Author keywords

Anthracene; Catalysis; Iron; Oxidation; Phthalocyanine

Indexed keywords

ANTHRACENE; CATALYSTS; CATALYTIC OXIDATION; IRON COMPOUNDS; ISOTOPES; KETONES; OXYGEN; PORPHYRINS; POTASSIUM COMPOUNDS;

ACTIVE SPECIES; BENZO(A)PYRENE; BENZO[A]ANTHRACENE; CATALYSE; INVERSE KINETIC ISOTOPE EFFECTS; ISOTOPE EFFECT; ISOTOPE OXYGENS; KINETIC ISOTOPES EFFECTS; LABELINGS; PHTHALOCYANINE;

CATALYSIS;

EID: 0001040706     PISSN: 14341948     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0682(199809)1998:9<1269::aid-ejic1269>3.0.co;2-g     Document Type: Article

References (61)

1. C. E. Cerniglia, Biodegradation 1992, 3, 351-368.
2. K. E. Hammel in Degradation of Environmental Pollutants by Microorganisms and their Metalloenzymes. Metal Ions in Biological Systems (Eds.: H. Sigel, A. Sigel), Marcel Dekker, New York, 1992, vol. 28, p. 41.
3. S. D. Haemmerli, M. S. A. Leisola, D. Sanglard, A. Fiechter, J. Biol. Chem. 1986, 261, 6900-6903.
4. K. E. Hammel, B. Kalyanaraman, T. K. Kirk, J. Biol. Chem. 1986, 261, 16948-16952.
5. J. D. Lipscomb, A. M. Orville in Degradation of Environmental Pollutants by Microorganisms and their Metalloenzymes. Metal Ions in Biological Systems (Eds.: H. Sigel, A. Sigel), Marcel Dekker, New York, 1992. vol. 28, p. 243.
6. D. A. Lane in Chemical Analysis of Polycyclic Aromatic Compounds (Ed.: T. Vo-Dinh), Wiley, New York, 1989, p. 31.
7. For a review on chemistry of polyarenes see: R. G. Harvey, Polycyclic Aromatic Compounds, Wiley, New York, 1997, p. 96.
8. M. Juaristi, J. M. Aizpurua, B. Lecea, C. Palomo, Can. J. Chem. 1984, 62, 2941-2944.
9. E. V. Dchmlov, J. K. Makrandi, J. Chem. Research (S) 1986, 32-33.
10. D. Villemin, M. Ricard, Nouv. J. Chem. 1984, 8, 185-189.
11. W. Adam, P. A.Ganeshpure, Synthesis 1993, 280-282.
12. [12a] R. Song, A. Sorokin, J. Bernadou, B. Meunier, J. Org. Chem. 1997, 62, 673-678.
13. [12b] G. J. Harden, M. M. Coombs, J. Chem. Soc., Perkin Trans. 1 1995, 3037-3042.
14. T. Higuchi, C. Satake, M. Hirobe, J. Am. Chem. Soc. 1995, 117, 8879-8880.
15. S. V. Barkanova, V. M. Derkacheva, O. V. Dolotova, V. D. Li, V. M. Negrimovsky, O. L. Kaliya, E. A. Luk'yanets, Tetrahedron Lett. 1996, 37, 1637-1640.
16. [15a] A Sorokin, J.-L. Séris, B. Meunier, Science 1995, 268, 1163-1166.
17. [15b] B. Meunier, A. Sorokin, Acc. Chem. Soc. 1997, 30, 470-476.
18. [16a] A. Sorokin, B. Meunier, Chem. Eur. J. 1996, 2, 1308-1317.
19. [16b] A. Sorokin, S. De Suzzoni-Dezard, D. Poullain, J.-P. Noël, B. Meunier, J. Am. Chem Soc. 1996, 118, 7410-7411.
20. [16c] A. Hadasch, A. Sorokin, A. Rabion, B. Meunier, New J. Chem. 1998, 45-51.
21. A. Sorokin, L. Fraisse, A. Rabion, B. Meunier, J. Mol. Cat. 1997, 117. 103-114.
22. R. J. Lorentzen, J. Caspary, S. A. Lesko, P. O. Ts'o, Biochemistry 1975, 14, 3970-3977.
23. L. Melander, J. M. Saunders, Reaction Rates of Isotopic Molecules, Wiley, New York, 1980, p. 95.
24. [20a] J. Bernadou, A.-S. Fabiano, A. Robert, B. Meunier, J. Am. Chem. Soc. 1994, 116, 9375-9376.
25. [20b] M. Pitié, J. Bernadou, B. Meunier, J. Am. Chem. Soc. 1995, 117, 2935-2936.
26. [2oc] R. J. Balahura, A. Sorokin, J. Bernadou, B. Meunier, Inorg. Chem. 1997, 36, 3488-3492.
27. [21a] W. Nam, J. S. Valentine, J. Am. Chem. Soc. 1993, 115, 1772-1778.
28. [21b] K. A. Lee, W. Nam, J. Am. Chem. Soc. 1997, 119, 1916-1922.
29. [21c] J. T. Groves, J. Lee. S. S. Maria, J. Am Chem. Soc. 1997, 119, 6269-6273.
30. B. Meunier, Chem. Rev. 1992, 92, 1411-1456.
31. [23a] T. J. McMurry, J. T. Groves, In Cytochrome P-450 Structure, Mechanism and Biochemistry (Ed.: P. R. Ortiz de Montellano), Plenum, New York, 1986; pp. 1-28.
32. [23b] M. Newcomb, M.-H. Le Tadic-Biadatti, D. L. Chestney, E. S. Roberts, P. F. Hollenberg, J. Am Chem. Soc. 1995, 117, 12085-12091.
33. R. A. Poirier, Y. Wang, K. C. Westaway, J. Am. Chem. Soc. 1994, 116, 2526-2533.
34. S. Wolfe, C.-K. Kirn, J. Am. Chem. Soc. 1991, 113, 8056-8061.
35. [26a] P. A. Nielsen; S. S. Glad, F. Jensen, J. Am. Chem. Soc. 1996, 118, 10577-10583.
36. [26b] S. S. Glad, F. Jensen, J. Am. Chem. Soc. 1997, 119, 227-232.
37. [27a] R. P. Hanzlik, G. O. Shearer, Biochem. Pharm. 1978, 27, 1441-1444 and references therein.
38. [27b] A. K. Bhattacharjee, M. K. Mahanti, Gazz. Chim. Ital. 1984, 114, 337-340.
39. G. W. Griffin, K. A. Horn, J Am Chem. Soc. 1987, 109, 4919-4926 and references therein.
40. G. Vassilikogiannakis, M. Orfanopoulos, J. Am. Chem. Soc. 1997, 119, 7394-7395.
41. K. R. Korzekwa, D. C. Swinney, W. F. Trager, Biochemistry 1989, 28, 9019-9027.
42. R. P. Hanzlik, K.-H. J. Ling, J. Am. Chem. Soc. 1993, 115, 9363-9370.
43. G. Tian, S.-Y. Chen, K. L. Facchine, S. R. Prakash, J. Am. Chem. Soc. 1995, 117, 2369-2370.
44. K. A. Kurtz, P. F. Fitzpatrick, J Am. Chem. Soc. 1997, 119, 1155-1156.
45. J. March, Advanced Organic Chemistry: Reactions, Mechanisms and Structure, 4th ed., Wiley, New York, 1992, p. 20.
46. L. Melander, R. E. Carter, Acta Chem. Scand. 1964, 18, 1138-1149.
47. K. Mislow, R. Graeve, A. J. Gordon, G. H. Wahl, Jr., J. Am. Chem. Soc 1963, 85, 1199-1200.
48. R. W. Nagorski, H. Slebocka-Tilk, R. S. Brown, J. Am. Chem. Soc. 1994, 116, 419-420.
49. [38a] D. Rabinovich, G. Parkin, J. Am. Chem. Soc 1993, 115, 353-354.
50. [38b] R. H. Schultz, A. A. Bengali, M. J. Tauber, B. H. Weiller, E. P Wasserman, K. R. Kyle, C. B. Moore, R. G. Bergman, J. Am. Chem. Soc. 1994, 116, 7369-7377.
51. M. J. Tanner, M. Brookhart, J. M. DeSimone, J. Am. Chem. Soc. 1997, 119. 7617-7618.
52. D. R. Evans, T. Drovetskaya, R. Bau, C. A. Reed, P. D. W. Boyd, J. Am. Chem. Soc. 1997, 119, 3633-3634.
53. Z. Xie, R. Bau, C. A. Reed, Angew. Chem. Int. Ed. Engl. 1994, 33, 2433-2434.
54. [7], p. 26.
55. T. R. Criswell, B. H. Klanderman, J. Org. Chem. 1974, 39, 770-774.
56. K. Brederesk, E. F. Sommermann, Tetrahedron Lett. 1966, 41, 5009-5014.
57. S. A. Carlson, D. H. Hercules, Anal. Chem. 1973, 45, 1794-1799.
58. P. P. Fu, R. G. Harvey, Chem. Rev. 1978, 78, 317-361.
59. J. H. Weber, D. H. Busch, Inorg. Chem. 1965, 4, 469-471.
60. P. Hoffmann, G. Labat, A. Robert, B. Meunier, Tetrahedron Lett. 1990, 31, 1991-1994.
61. B. H. Han, P. Boudjouk, Tetrahedron Lett. 1982, 23, 1643-1646.