Reductive cleavage mechanism of methylcobalamin: Elementary steps of Co-C bond breaking

Journal of Physical Chemistry B

Volumn 111, Issue 26, 2007, Pages 7638-7645

  Kozlowski, Pawel M ^a   Kuta, Jadwiga ^a   Galezowski, Wlodzimierz ^b  

^a UNIVERSITY OF LOUISVILLE   (United States)

^b ADAM MICKIEWICZ UNIVERSITY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

DENSITY FUNCTIONAL THEORY; DISSOCIATION; MOLECULAR INTERACTIONS; NEGATIVE IONS; PHASE EQUILIBRIA;

EQUILIBRIUM GEOMETRY; METHYLCOBALAMIN; REDUCTIVE CLEAVAGE MECHANISM;

CHEMICAL BONDS;

EID: 34547438769     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp066972w     Document Type: Article

References (77)

1. 12; Dolphin, D. Ed.; Wiley-Interscience: New York, 1982.
2. (b) Banerjee, R. Chem. Biol. 1997, 4, 175-186.
3. (c) Ludwig, M. L.; Matthews, R. G. Annu. Rev. Biochem. 1997, 66, 269-313.
4. 12 Proteins; Kräutler, B., Arigoni, D., Golding, B.T. Eds.; Wiley-VCH: New York, 1998.
5. (e) Marzilli, L.G. in Bioinorganic Catalysis Reedijk, J., Bouwman, E. Eds.; Marcel Dekker: New York, 1999; pp 423-468.
6. 12; John Wiley & Sons: New York, 1999.
7. (g) Toraya, T. Cell. MoI. Life Sci. 2000, 57, 106-127.
8. (h) Banerjee, R., Biochem. 2001, 40, 6191-6198.
9. (i)O Banerjee, R.; Ragsdale, S. W. Annu. Rev. Biochem. 2003, 72, 209-247.
10. (j) Banerjee, R. Chem. Rev. 2003, 103, 2083-2094.
11. (k) Toraya, T. Chem. Rev. 2003, 103, 2095-2127.
12. (l)O Brown, K. L. Chem. Rev. 2005, 105, 2075-2149.
13. (m)O Randaccio, L.; Geremia, S.; J.; Wuerges, J. Organomet. Chem. 2007, 692, 1198-1215.
14. Matthews, R. G. Ace Chem. Res. 2001, 34, 681-689.
15. N2-type, and the presence of free carbocations is not involved. Alternative mechanisms have been postulated for methyl transfer including oxidative addition and single electron transfer (see ref 2 for details).
16. Halpern, J. Science 1985, 227, 869-875.
17. (a) Finke, R. G.; Hay, B. P. Inorg. Chem. 1984, 23, 3041-3043.
18. (b) Hay, B. P.; Finke, R. G. J. Am. Chem. Soc. 1986, 108, 4820-4829.
19. 12 Proteins; Kräutler, B., Arigoni, D., Golding, B.T., Eds.; Wiley-VCH: Weinheim, Germany, 1998; Chapter 25.
20. (a) Hay, B. P.; Finke, R. G. Polyhedron 1988, 7, 1469-1481.
21. (b) Luo, L. B.; Li, G.; Chen, H. L.; Fu, S. W.; Zhang, S. Y. J. Chem. Soc., Dalton Trans. 1998, 2103-2107.
22. (a) Lexa, D.; Savèant, J-M. J. Am. Chem. Soc. 1978, 100, 3220-3222.
23. (b) Lexa, D.; Savèant, J-M. Ace Chem. Res. 1983, 16, 235-243.
24. Kim, M.-H.; Birke, R. L. J. Electroanal Chem. 1983, 144, 331-350.
25. Ohkubo, K.; Fukuzumi, S. J. Phys. Chem. A 2005, 109, 1105-1113.
26. Birke, R. L.; Huang, Q.; Spataru, T.; Gosser, D. K. Jr. J. Am. Chem. Soc. 2006, 128, 1922-1936.
27. Spataru, T.; Birke, R. L. J. Electroanal. Chem. 2006, 593, 74-86.
28. Martin, B. D.; Finke, R. G. J. Am. Chem. Soc. 1992, 114, 585-592.
29. .-, should be significantly elongated. See, for details Antonello, S.;
30. Daasbjerg, K.; Jensen, H.; Taddei, F.; Maran, F. J. Am. Chem. Soc. 2003, 125, 14905-14916.
31. Salem, L.; Eisenstein, O.; Anh, N. T.; Bürgi, H. B.; Devaquet, A.; Segal, G, Veillard, A. Nouv. J. Chim. 1977, 1, 335 - 348.
32. Stich, T. R.; Brooks, A. J; Buan., N. R.; Brunold, T. C. J. Am. Chem. Soc. 2003, 125, 5897-5914.
33. Jaworska, M.; Lodowski, P.; Andruniow, T.; Kozlowski. P. M. J. Phys. Chem. B 2007, 111, 2419-2422.
34. (a) Savèant, J-M. Acc. Chem. Res. 1993, 26, 455-461.
35. (b) Savèant, J-M Adv. Phys. Org. Chem. 2000, 35, 117-192.
36. Spataru, T.; Birke, R. L. J. Phys. Chem. A 2006, 110, 8599-8604.
37. Spataru and Birke (ref 19) assumed that the length of the Co-C bond for the one-electron reduced species should be substantially elongated in comparison to the neutral cofactor. However, there is no experimental evidence to support this claim, and the low dissociation energy itself is not indicative that the Co-C bond length should be perturbed upon addition of an electron. Furthermore, the results of CASSCF calculations must be further improved by the addition of dynamical correlation, which is usually treated via second-order perturbation theory (CASPT2).
38. Runge, E.; Gross, E. K. U. Phys. Rev. Lett. 1984, 52, 997-1000.
39. (a) Baerends, E. J.; Ricciardi, G.; Rosa, A.; van Gisbergen, S. J. A. Coord. Chem. Rev. 2002, 230, 5-27.
40. (b) Dreuw, A.; Head-Gordon, M. Chem. Rev. 2005, 105, 4009-4037.
41. (c) Dreuw, A. ChemPhysChem 2006, 7, 2259-2274.
42. (a) Becke, A. D. J. Chem. Phys. 1986, 84, 4524-4529.
43. (b) Perdew, J. P. Phys. Rev. B 1986, 33, 8822-8824.
44. Frisch M. J. et al., Gaussian 03, Revision C.02; Gaussian, Inc.: Wallingford, CT, 2004 (for full reference see Supporting Information).
45. Jensen, K. P.; Ryde, U. J. Phys. Chem. A 2003, 107, 7539-7545.
46. (a) Rovira, C.; Biarnes, X.; Kunc, K. Inorg. Chem. 2004, 43, 6628-6632.
47. (b) Rovira, C.; Kozlowski, P. M. J. Phys. Chem. B 2007, 111, 3251-3257.
48. Dölker, N.; Morreale, A.; Maseras, F. J. Biol. Inorg. Chem. 2005, 10, 509-517.
49. Pratt, D. A.; van der Donk, W. J. Am. Chem. Soc. 2005, 127, 384-396.
50. Kuta, J.; Patchkovskii, S.; Zgierski, M. Z.; Kozlowski, P. M. J. Comput. Chem. 2006, 27, 1429-1437.
51. Kozlowski, P. M.; Kamachi, T.; Toraya, T.; Yoshizawa, K. Angew. Chem., Int. Ed. 2007, 46, 980-983.
52. (a) Randaccio, L.; Furlan, M.; Geremia, S.; Slouf, M.; Srnova, I.; Toffoli, D. Inorg. Chem. 2000, 39, 3403-3413.
53. (b) Randaccio, L.; Geremia, S.; Nardin, G.; Wuerges, J. Coord. Chem. Rev. 2006, 250, 1332-1350.
54. Hung, R. R.; Grabowski J. J. J. Am. Chem. Soc. 1999, 121, 1359-1364.
55. Andruniow, T.; Kuta, J.; Zgierski, M. Z.; Kozlowski, P. M. Chem. Phys. Lett. 2005, 470, 410-416.
56. The single-reference TD-DFT method is not capable of providing any detailed description when the crossing of two curves take place. Only an estimate can be obtained based on energy interpolation. However, the analysis of vertical excitations outside of this range provides a clue as to which states should be connected, and therefore the overall picture is not affected by such interpolation.
57. Jensen, K. P.; Ryde, U. ChemBioChem 2003, 4, 413-424.
58. Jensen, K. P. J Phys. Chem. B 2005, 109, 10505-10512.
59. Lorance, E. D.; Kramer, W. H.; Gould, I. R. J. Am. Chem. Soc. 2002, 124, 15225-15238.
60. Laage, D.; Burghardt, I.; Sommerfeld, T.; Hynes, J. T. ChemPhysChem 2003, 4, 61-66.
61. (a) Laage, D.; Burghardt, I.; Sommerfeld, T.; Hynes, J. T. J. Phys. Chem. A 2003, 107, 11271-11291.
62. (b) Burghardt, I.; Laage, D.; Hynes, J. T. J. Phys. Chem. A 2003, 107, 11292-11306.
63. Takeda, N.; Poliakov, P. V.; Cook, A. R.; Miller, J. R. J. Am. Chem. Soc. 2004, 126, 4301-4309.
64. Costentin, C.; Robert, M.; Savèant, J-M. J. Am. Chem. Soc. 2004, 126, 16051-16057.
65. Antonello, S.; Maran, F. Chem. Soc. Rev. 2005, 34, 418-428.
66. Simons, J. Ace. Chem. Res. 2006, 39, 772-779.
67. Brown, K. L.; Peck-Siler, S. Inorg. Chem. 1988, 27, 3548-3555.
68. +.
69. Sirovatka-Dorweiler, J.; Matthews, R. G.; Finke, R. G. Inorg. Chem. 2002, 47, 6217-6224.
70. 7a
71. transl values that are too large in aqueous solution; see for example Amzel, L. M. Proteins: Struct., Fund., Genet. 1997, 28, 144-149.
72. Finke, R. G.; Martin, B. D. J. Inorg. Biochem. 1990, 40, 19-22.
73. 12 cofactors.
74. Jensen, K. P.; Ryde, U. J. Am. Chem. Soc. 2003, 125, 13970-13971.
75. Marcus, R. A. J. Phys. Chem. A 1997, 101, 4072-4087.
76. N2 Mechanism; Wiley-Interscience: New York, 1992.
77. Costentin, C.; Robert, M.; Savèant, J-M. J. Am. Chem. Soc. 2004, 126, 16834-16840.