Monomeric MnIII/II and FeIII/II Complexes with Terminal Hydroxo and Oxo Ligands: Probing Reactivity via O-H Bond Dissociation Energies

Journal of the American Chemical Society

Volumn 125, Issue 43, 2003, Pages 13234-13242

  Gupta, Rajeev ^a   Borovik, A S ^a  

^a UNIVERSITY OF KANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LIGANDS;

DISSOCIATION; HYDROGEN; IRON; MANGANESE; SUBSTRATES; THERMODYNAMICS;

COMPLEXATION;

1,4 CYCLOHEXADIENE; 9,10 DIHYDROANTHRACENE; ALKADIENE; ALKALOID; ANTHRACENE DERIVATIVE; HYDROXIDE; IRON DERIVATIVE; LIGAND; MANGANESE DERIVATIVE; METALLOPROTEIN; OXOACID; TEMPOL; TRIS[(N' TERT BUTYLUREAYLATO) N ETHYL]AMINATE; UNCLASSIFIED DRUG; UREA DERIVATIVE; FERRIC ION; FERROUS ION; MANGANESE; ORGANOMETALLIC COMPOUND; PHENOL DERIVATIVE;

ARTICLE; CHEMICAL BINDING; CHEMICAL REACTION KINETICS; COMPLEX FORMATION; DISSOCIATION; ENERGY; HYDROGEN BOND; ISOLATION PROCEDURE; METAL BINDING; PROTON TRANSPORT; REACTION ANALYSIS; THERMODYNAMICS; CHEMISTRY; ELECTROCHEMISTRY; ELECTRON SPIN RESONANCE; KINETICS;

ELECTROCHEMISTRY; ELECTRON SPIN RESONANCE SPECTROSCOPY; FERRIC COMPOUNDS; FERROUS COMPOUNDS; HYDROXIDES; KINETICS; LIGANDS; MANGANESE; ORGANOMETALLIC COMPOUNDS; PHENOLS; THERMODYNAMICS;

EID: 0142151778     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja030149l     Document Type: Article

References (56)

1. Nelson, M. J.; Seitz, S. P. In Active Oxygen in Biochemistry; Valentine, J. S., Foote, C. S., Greenberg, A., Liebman, J. F., Eds.; Blackie Academic & Professional: London, 1995; Vol. 3.
2. Su, C.; Sahlin, M.; Oliw, E. H. J. Biol. Chem. 2000, 275, 18830-18835.
3. (a) Merkx, M.; Kopp, D. A.; Sazinsky, M. H.; Blazyk, J. L.; Müller, J.; Lippard, S. J. Angew. Chem. Int. Ed. 2001, 40, 2782-2807.
4. (b) Que, L., Jr.; Tolman, W. B. Angew. Chem., Int. Ed. 2002, 41, 1114-1137.
5. (a) Wallar, B. J.; Lispcomb, J. D. Chem. Rev. 1996, 96, 2625-2657 and references therein.
6. (b) Feig, A. L.; Lippard, S. J. Chem. Rev. 1994, 94, 759-805 and references therein.
7. (c) Stubbe, J. J. Biol. Chem. 1990, 265, 5329.
8. (a) Tommos, C.; Babcock, G. T. Acc. Chem. Res. 1998, 31, 18-25 and references therein.
9. (b) Gilchrist, M. L., Jr.; Ball, J. A.; Randall, D. W.; Britt, R. D. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 9545-9549.
10. (c) Tang, X.-S.; Ball, J. A.; Randall, D. W.; Force, D. A.; Diner, B. A. ; Britt, R. D. J. Am. Chem. Soc. 1996, 118, 7638-7639.
11. (d) Pecoraro, V. L.; Baldwin, M. J.; Caudle, M. T.; Hsieh, W.-Y.; Law, N. A. Pure Appl. Chem. 1998, 70, 925-929.
12. (a) Gardner, K. A.; Mayer, J. M. Science 1995, 269, 1849-1851.
13. (b) Gardner, K. A.; Kuehnert, L. L.; Mayer, J. M. Inorg. Chem. 1997, 36, 2069-2078.
14. (c) Wang, K.; Mayer, J. M. J. Am. Chem. Soc. 1997, 119, 1470-1471.
15. (d) Mayer, J. M. Acc. Chem. Res. 1998, 31, 441-450 and references therein.
16. (e) Mayer, J. M. In Biomimetic Oxidations Catalyzed by Transition Metal Complexes; Meunier, B., Ed.; Imperial College Press: London, 2000; pp 1-43 and references therein.
17. 6e it is reasonable to assume that in our systems the entropy change is insignificant because the molecules involved are relatively large and differ only by a hydrogen atom.
18. (a) Baldwin, M. J.; Pecoraro, V. L. J. Am. Chem. Soc. 1996, 118, 11325-11326.
19. (b) See ref 6c.
20. Caudle, M. T.; Pecoraro, V. L. J. Am. Chem. Soc. 1997, 119, 3415-3416.
21. (a) Jonas, R. T.; Stack, T. D. P. J. Am. Chem. Soc. 1997, 119, 8566-8567.
22. (b) Goldsmith, C. R.; Jonas, R. T.; Stack, T. D. P. J. Am. Chem. Soc. 2002, 124, 83-96.
23. Gupta, R.; MacBeth, C. E.; Young, V. G., Jr.; Borovik, A. S. J. Am. Chem. Soc. 2002, 124, 1136-1137.
24. (a) Hammes, B. S.; Young, V. G., Jr.; Borovik, A. S. Angew. Chem., Int., Ed. 1999, 38, 666-669.
25. (b) Shirin, Z.; Hammes, B. S.; Young, V. G., Jr.; Borovik, A. S. J. Am. Chem. Soc. 2000, 122, 1836-1837.
26. (c) MacBeth, C. E.; Golombek, A. P.; Young, V. G., Jr.; Yang, C.; Kuczera, K.; Hendrich, M. P.; Borovik, A. S. Science, 2000, 289, 938-941.
27. (d) MacBeth, C. E.; Hammes, B. S.; Young, V. G., Jr.; Borovik, A. S. Inorg. Chem. 2001, 40, 4733-4741.
28. Bordwell, F. G.; Liu, W.-Z. J. Am. Chem. Soc. 1996, 118, 10819-10823.
29. Bordwell, F. G. Acc. Chem. Res. 1988, 21, 456-463.
30. Binstead, R. A.; Zuberbuhler, A. D. Spectfit; Spectrum Associates: Chapel Hill, NC, 1993-97.
31. Ray, M.; Hammes, B. S.; Yap, G. P. A.; Rheingold, A. H.; Liable-Sands, L.; Borovik, A. S. Inorg. Chem. 1998, 37, 1527-1532.
32. Landgrebe, J. A. Organic Laboratory, 4th ed.; Brooks/Cole: Pacific Grove, CA, 1993.
33. For discussions on the effects of the secondary coordination, particularly those of hydrogen bonds, on the function of active sites in protein, see: (a) Ozaki, S.; Roach, M. P.; Matsui, T.; Watanabe, Y. Acc. Chem. Res. 2001, 34, 818-825.
34. (b) Yikilmaz, E.; Xie, J.; Brunold, T. C.; Miller, A.-F. J. Am. Chem. Soc. 2002, 124, 3482-3483.
35. (c) Xie, J.; Yikilmaz, E.; Miller, A.-F.; Brunold, T. C. J. Am. Chem. Soc. 2002, 124, 3769-3774.
36. (d) Maliekal, J.; Karapetian, A.; Vance, C.; Yikilmaz, E.; Wu, Q.; Jackson, T.; Brunold, T. C.; Spiro, T. G.; Miller, A.-F. J. Am. Chem. Soc. 2002, 124, 15064-15075.
37. (e) Jackson, T. A.; Xie, J.; Yikilmaz, E.; Miller, A.-F.; Brunold, T. C. J. Am. Chem. Soc. 2002, 124, 10833-10845.
38. +/Fc in DMSO is approximately -0.65 V.
39. -/2- couple only changes by 6 mV (-0.016 versus -0.022 mV) for the higher velocity CV compared to that measured at the scan velocity of 0.1V/s.
40. (a) Bordwell, F. G.; Cheng, J.-P.; Ji, G.-Z.; Satish, A. V.; Zhang, X. J. Am. Chem. Soc. 1991, 113, 9790-9795.
41. (b) Parker, V. D.; Handoo, K. L.; Roness, F.; Tilset, M. J. Am. Chem. Soc. 1991, 113, 7493-7498.
42. 2-salicylideneamino)propane (X = Cl, H, di-tert-butyl).
43. (a) Siegbahn, P. E. M. Inorg. Chem. 2000, 39, 2923-2935.
44. (b) Blomberg, M. R. A.; Siegbahn, P. E. M. Theor. Chem. Acc. 1997, 97, 72-80.
45. 6c
46. Determined by gas chromatography; see Experimental Section.
47. CRC Handbook of Chemistry and Physics, 72nd ed.; Lide, D. R., Ed.: CRC Press: Boca Raton, FL, 1991; pp 9-115.
48. C-H of 78 kcal/mol for DHA is for the transfer of the first H-atom, while the second H-atom transfer requires only ∼43 kcal/mol. This irreversible second step drives the overall reaction towards completion: (a) Mulder, P.; Hemmink, S.; De Heer, M. I.; Lupo, M.; Santoro, D.; Korth, H.-G. J. Org. Chem. 2001, 66, 6611-6619.
49. (b) Malhotra, R.; McMillen, D. F. Energy Fuels 1990, 4, 184-193.
50. Peduli, G. F.; Lucarini, M.; Pedrielli, P.; Cabiddu, S.; Fattuoni, C. J. Org. Chem. 1996, 61, 9259-9263.
51. Cook, C. D.; Kuhn, D. A.; Fianu, P. J. Am. Chem. Soc. 1955, 78, 2002-2005.
52. 14
53. (a) Martell, A. E.; Smith, R. M. Critical Stability Constants; Plenum: New York, 1976; Vol. IV, p 1.
54. (b) CRC Handbook of Chemistry and Physics, 72nd ed.; Lide, D. R., Ed.; CRC Press: Boca Raton, FL, 1991; pp 9-115.
55. Zouri, A.; Witt, H. T.; Kern, J.; Fromme, P.; Krauss, N.; Saenger, W.; Orth, P. Nature 2001, 409, 739-743.
56. Blanksby, S. J.; Ellison, G. B. Acc. Chem. Res. 2003, 36, 255-263.