Determination of the C4-H bond dissociation energies of NADH models and their radical cations in acetonitrile

Chemistry - A European Journal

Volumn 9, Issue 4, 2003, Pages 871-880

  Zhu, Xiao Qing ^a   Li, Hai Rong ^a   Li, Qian ^a   Ai, Teng ^a   Lu, Jin Yong ^a   Yang, Yuan ^a   Cheng, Jin Pei ^a  

^a NANKAI UNIVERSITY   (China)

Author keywords

Bond energy; Calorimetry; Effective charge; NADH models; Radical ions

Indexed keywords

ACETONITRILE; CALORIMETRY; DERIVATIVES; DISSOCIATION; ELECTROCHEMISTRY; FREE ENERGY; POSITIVE IONS; PROTONS; THERMODYNAMICS; TITRATION;

RADICAL CATIONS;

HYDROGEN BONDS;

1 BENZYL 1,4 DIHYDRONICOTINAMIDE; 1,4 DIHYDRONICOTINAMIDE DERIVATIVE; 1,4 DIHYDROPYRIDINE DERIVATIVE; ACETONITRILE; ACRIDAN; ACRIDINE DERIVATIVE; CARBON; CATION; HYDROGEN; N,N,N',N' TETRAMETHYL 4 PHENYLENEDIAMINE; NICOTINAMIDE DERIVATIVE; PERCHLORATE; RADICAL; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE; UNCLASSIFIED DRUG;

ARTICLE; CALORIMETRY; CHEMICAL BOND; CHEMICAL STRUCTURE; DISSOCIATION; ELECTROCHEMISTRY; ENERGY; PROTON TRANSPORT; REACTION ANALYSIS; STRUCTURE ANALYSIS; THERMODYNAMICS; TITRIMETRY;

ACETONITRILES; CALIBRATION; CALORIMETRY; CATIONS; CHEMISTRY, PHYSICAL; DIHYDROPYRIDINES; ELECTROCHEMISTRY; INDICATORS AND REAGENTS; MODELS, CHEMICAL; NAD; OXIDANTS; THERMODYNAMICS;

EID: 0037450133     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200390108     Document Type: Article

References (96)

1. a) Y. Murakami, J. Kikuchi, Y. Hisaeda, O. Hayashida, Chem. Rev. 1996, 96, 721;
2. b) M. E. Brewster, A. Simay, K. Czako, D. Winwood, H. Farag, N. Bodor, J. Org. Chem. 1989, 54, 3721;
3. C) F. Friedlos, R.J. Knox, Biochem. Pharmacol. 1992, 44, 631.
4. a) X.-Q. Zhu, Y. Liu, B. J. Zhao, J.-P. Cheng, J. Org. Chem. 2001, 66, 370;
5. b) X.-Q. Zhu, H.-Y. Wang, J.-S. Wang, Y.-C. Liu, J. Org. Chem. 2001, 66, 344;
6. c) X.-Q. Zhu, B.-J. Zhao, J.-P. Cheng, J. Org. Chem. 2000, 65, 8158;
7. d) X.-Q. Zhu, Y.-C. Liu, J.-P. Cheng, J. Org. Chem. 1999, 64, 8980;
8. e) X.-Q. Zhu, Y.-C. Liu, H.-Y. Wang, W. Wang, J. Org. Chem. 1999, 64, 8982;
9. f) X.-Q. Zhu, Y.-C. Liu, J. Org. Chem. 1998, 63, 2786;
10. g) X.-Q. Zhu, H.-L. Zou, P.-W. Yuan, L. Cao, J.-P. Cheng, J. Chem. Soc. Perkin Trans. 2 2000, 1857;
11. h) X.-Q. Zhu, Y. Liu, B.-J. Zhao, J.-P. Cheng, J. Org. Chem. 2001, 66, 370.
12. a) T. Bally, P. Bednarek, J. Phys. Chem. A 2000, 104, 724;
13. b) P. Bednarek, T. Bally, J. Phys. Chem. A 2000, 104, 718;
14. c) N. Kanomata. T. Nakata, J. Am. Chem. Soc. 2000, 122, 4563;
15. d) A. Marcinek, J. Adamus, K. Huben, J. Gbicki, T. J. Bartczak, P. Bednarek, T. Bally, J. Am. Chem. Soc. 2000, 122, 437;
16. e) S. Fukuzumi, H. Imahori, K. Okamoto, H. Yamada, M. Fujitsuka, O. Ito, D. M. Guldi, J. Phys. Chem. A 2002, 106, 1903;
17. f) I. Nakanishi, S. Fukuzumi, T. Konishi, K. Ohkubo, M. Fujitsuka, O. Ito, N. Miyata, J. Phys. Chem. B 2002, 106, 2372;
18. g) H. C. Lo, C. Leiva, O. Buriez, J. B. Kerr, M. M. Olmstead, R. H. Fish, Inorg. Chem. 2001, 40, 6705;
19. h) J. Luo, T. C. Bruice, J. Am. Chem. Soc. 2001, 123, 11952;
20. i) S. Fukuzumi, Y. Fujii, T Suenobu, J. Am. Chem. Soc. 2001, 123, 10191;
21. j) B. Nidetzky, M. Klimacek, P. Mayr, Biochem. 2001, 40, 10371.
22. a) M. F. Powell, T. C. Bruice, J. Am. Chem. Soc. 1982, 104, 5834;
23. b) M. F. Powell, T. C. Bruice, J. Am. Chem. Soc. 1983, 105, 1014;
24. c) J. W. Verhoeven, W. van Gerresheim, F. M. Martiens, S. M. van der Kerk, Tetrahedron 1986, 42, 975;
25. d) L. L. Miller, J. R. Valentine, J. Am. Chem. Soc. 1988, 110, 3982;
26. e) D. Ostovic, R. M. G. Roberts, M. M. Kreevoy, J. Am. Chem. Soc. 1983, 105, 7629.
27. a) F. Powell, S. C. Wu, T. C. Bruice, J. Am. Chem. Soc. 1984, 106, 3850;
28. b) B. W. Carlson, L. L. Miller, J. Am. Chem. Soc. 1983, 105, 7453;
29. c) S. Fukuzumi, S. Koumitsu, K. Hironaka, T. Tanaka, J. Am. Chem. Soc. 1987, 109, 305;
30. d) A. Sinha, T. C. Bruice, J. Am. Chem. Soc. 1984, 106, 7291;
31. e) C, C. Lai, A, K. Colter, J. Chem. Soc. Chem. Commun. 1980, 1115.
32. a) L. L. Miller, J. R. Valentine, J. Am. Chem. Soc. 1988, 110, 3982, and references therein;
33. b) B. W, Carlson, L, L, Miller, J. Am. Chem. Soc. 1985, 107. 479;
34. c) S. Fukuzumi, S. Koumitsu, K. Hironaka, T. Tanaka, J. Am. Chem. Soc. 1987, 109, 305, and references therein;
35. d) S. Fukuznmi, N. Nishizawa, T. Tanaka, J. Org. Chem. 1984, 49, 3571;
36. e) C. A. Coleman, J. G. Rose, C. J. Murray, J. Am. Chem. Soc. 1992, 114, 9755.
37. a) P. Varnai, A. Warshel, J. Am. Chem. Soc. 2000, 122, 3849;
38. b) A. Yadav, R. M. Jackson, J. J. Holbrook, A. Warshel, J. Am. Chem. Soc. 1991, 113, 4800.
39. a) A. Anne, P. Hapiot, J. Moiroux, P. Neta, J.-M. Saveant, J. Am. Chem. Soc. 1992, 114, 4694;
40. b) A. Anne, S. Fraoua, V. Grass, J. Moiroux, J.-M. Saveant, J. Am. Chem. Soc. 1998, 120, 2951;
41. c) A. Anne, S. Fraoua, J. Moiroux, J.-M. Saveant, J. Am. Chem. Soc. 1996, 118, 3938;
42. d) P. Hapiot, J. Moiroux, J.-M. Saveant, J. Am. Chem. Soc. 1990, 112, 1337;
43. e) A. Anne, J. Moiroux, J. Org. Chem. 1990, 55, 4608.
44. J. Klippenstein, P. Arya, D. D. Wayner, J. Org. Chem. 1991, 56, 6736.
45. K. L. Handoo, J.-P. Cheng, V. D. Parker, J. Am. Chem. Soc. 1993, 115, 5067.
46. W. S. Matthews, J. E. Bares, J. E. Bartmess, F. G. Bordwell, F. J. Cornforth, G. E. Drucker, Z. Margonlin, R. J. McCallum, G. J. McCollum, N. R. Vanier, J. Am. Chem. Soc. 1975, 97, 7006.
47. E. Arnett, K. Amarnath, N. G. Harvey, J.-P. Cheng, J. Am. Chem. Soc. 1990, 112, 344.
48. a) D. E. Berning, B. C. Noll, D. L. DuBois, J. Am. Chem. Soc. 1999, 121 11432;
49. b) M. Tilset, V. D. Parker, J. Am. Chem. Soc. 1989, 111, 6711;
50. c) G. Kiss, K. Zhang, S. L. Mukerjee, C. D. Hoff, G. C. Roper, J. Am. Chem. Soc. 1990, 112, 5657.
51. a) T. Yao, S. Musha, M. Munemori, Chem. Lett. 1974, 939;
52. b) E. P. Platonova, V. G. Kashechko, V. Y. Atamanyuk, V. D. Pokhodenko, Elektrokhimiya 1980, 16, 674.
53. Z.-L. Guo, Y.-C. Liu, Liu, Chin. Sci. Bull. 1988, 18, 1388.
54. In Equations (7) - (10), free-energy change ΔG was used to replace the enthalpy change ΔH for the electron transfer processes. This treatment is reasonable because the entropies associated with electron transfer have been verified by Arnett's work (see E. M. Arnett, K. Amarnath, N. G. Harvey, J. Cheng, J. Am. Chem. Soc. 1990, 112, 344). The main reason is that the molecular structures of the products and the corresponding reactants are similar for a single electron transfer.
55. -1, ref: S. Fukuzumi, K. Hironaka, N. Nishizawa, T. Tanaka, Bull. Chem. Soc. Jpn. 1983, 56, 2220).
56. J.-P. Cheng, K. L. Handoo, V. D. Parker, J. Am. Chem. Soc. 1993, 115, 2655.
57. C. J. Curtis, A. Miedaner, W. Ellis, D. L. DuBois, J. Am. Chem. Soc. 2002, 124, 1918.
58. a) A. van Laar, H. J. van Ramesdonk, J. W. Verhoeven, Recl. Trav. Chim. Pays-Bas 1983, 102, 157;
59. b) W. van Gerresheim, J. W. Verhoeven. Recl. Trav. Chim. Pays-Bas 1983, 102, 339.
60. Unlike heterolytic C-H bond scission energies, generally the BDE of the C-H bond is not very dependent on the nature of solvents.
61. X.-M. Zhang, F. G. Bordwell, J. Am. Chem. Soc. 1992, 114, 9787.
62. V. D. Parker, J. Am. Chem. Soc. 1992, 114, 7458.
63. D. D. Watner, V. D. Parker, Acc. Chem. Res. 1993, 26, 287.
64. D. D. Tanner, H. K. Singh, A. Kharrat, A. R. Stein, J. Org. Chem. 1987, 52, 2142.
65. E. S. Huyser, J. A. K. Harmony, F. L. McMillian, J. Am. Chem. Soc. 1972, 94, 3176.
66. a) S. Fukuzumi, T. Kitano, M. Ishikawa, J. Am. Chem. Soc. 1990, 112, 5631;
67. b) P. J. Elving in Topics in Bioelectrochemistry and Bioenergetics, Vol 1 (Ed. G. Milazzo), Wiley, New York, 1976, p. 179;
68. c) V. Carelli, F. Liberatore, A. Casini, R. Mondelli, A. Arnone, I. Carelli, G. Retilio, I. Mavelli, Bioorg. Chem. 1980, 9, 342;
69. d) S. Fukuzumi, T. Kitano, K. Mochida, J. Am. Chem. Soc. 1990, 122, 3246;
70. e) X.-Q. Zhu, Y.-C. Liu, J. Li, H. Y. Wang, J. Chem. Soc. Perkin Trans. 2 1997, 2191;
71. f) E. S. Huyser, J. A. K. Harmony, F. L. McMillian, J. Am. Chem. Soc. 1972, 94, 3176.
72. a) Y.-C. Liu, B. Li, Q. X. Guo, Tetrahedron Lett. 1994, 35, 8429;
73. b) Y.-C. Liu, B. Li, Q. X. Guo, Tetrahedron 1995, 51, 9671;
74. c) L. L. Miller, J. R. Valentine, J. Am. Chem. Soc. 1988, 110, 3982.
75. S. Fukuzumi, T. Kitano, Chem. Lett. 1990, 1275.
76. B. W. Carlson, L. L. Miller, P. Neta, J. Grodkowski, J. Am. Chem. Soc. 1984, 106, 7233.
77. A. Sinha. T. C. Bruice, J. Am. Chem. Soc. 1984, 106, 7291.
78. According to the Hammett equation log K = ρσ and ΔH ≈- RT log K, the line slope of ΔH against σ should be approximately equal to - 5.7 ρ.
79. a) M. Page, A. Williams, Organic and Bio-organic Mechanism, Longman, 1997, Chapter 3, pp. 52-79;
80. b) A. Williams, Acc. Chem. Res. 1984, 17, 425;
81. c) A. Williams, Acc. Chem. Res. 1989, 22, 387;
82. d) A. Williams, Adv. Phys. Org. Chem. 1991, 27, 1;
83. e) A. Williams, J. Am. Chem. Soc. 1985, 107, 6335;
84. X.-Q. Zhu, Q. Li, W.-F. Hao, J.-P. Cheng, J. Am. Chem. Soc. 2002, 124, 9887.
85. S. Fukuzumi, Y. Fujii, T. Suenobu, J. Am. Chem. Soc. 2001, 123, 10191.
86. C4-C4 dimers of radical BNA and its derivatives have been obtained from several experiments, which indicate that BNA should result from the C4 radical rather than the N1 radical.
87. a) D. F. McMillen, D. M. Golden, Annu. Rev. Phys. Chem. 1982, 33, 493;
88. b) J. M. Dust. D. R. Arnold, J. Am. Chem. Soc. 1983, 105, 1221, and references therein.
89. a) R. I. Walter, J. Am. Chem. Soc. 1966, 88, 1923;
90. b) F. G. Bordwell, J.-P. Cheng, J. Am. Chem. Soc. 1991, 113, 1736, and references therein;
91. c) J.-P. Cheng, Y. Lu, B. Liu, Y. Zhao, D. Wang, Y. Sun, J. Mi, Sci. China Ser. B 1998, 41, 215, and references therein.
92. A. C. Anderson. G. Berkelnammer, J. Am. Chem. Soc. 1958, 80, 992.
93. J. L. Kutz, R. Hutton, F. H. Westheimer, J. Am. Chem. Soc. 1961, 83, 584.
94. R. M. G. Roberts, D. Ostovic, M. M. Kreevoy, Faraday Discuss. Chem. Soc. 1982, 74, 257.
95. L. Michaelis, S. Granick, J. Am. Chem. Soc. 1943, 65, 1747.
96. F. T. Gucker, H. B. Pickard, R. W. Planck, J. Am. Chem. Soc. 1939, 61, 459.