Theoretical investigation of the isomerization of N2O3 and the N-nitrosation of dimethylamine by asym-N2O3, sym-N2O3, and trans-cis N2O3 isomers

Journal of Molecular Structure: THEOCHEM

Volumn 908, Issue 1-3, 2009, Pages 107-113

  Sun, Zhi ^a   Liu, Yong Dong ^a   Lv, Chun Lin ^a   Zhong, Ru Gang ^a  

^a BEIJING UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

Carcinogen; Isomerization; N Nitrosation; N2O3; NDMA

Indexed keywords

EID: 67649867944     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.theochem.2009.05.012     Document Type: Article

References (77)

1. Wink D.A., and Mitchell J.B. Free Radical Biol. Med. 25 (1998) 434
2. Grisham M.B., Heuil D.J., and Wink D.A. Am. J. Physiol. Gastrointest. Liver Physiol. 276 (1999) 315
3. Suzuki T., Mower H.F., Friesen M.D., Gilibert I., Sawa T., and Ohshima H. Free Radical Biol. Med. 37 (2004) 671
4. Wink D.A., Kasprzak K.S., Maragos C.M., Elespuru R.K., Misra M., Dunams T.M., Cebula T.A., Koch W.H., Andrews A.W., Allen J.S., and Keefer L.K. Science 254 (1991) 1001
5. Burney S., Caulfield J.L., Niles J.C., Wishnok J.S., and Tannenbaum S.R. Mutat. Res. 424 (1999) 37
6. Wiseman H., and Halliwell B. Biochem. J. 313 (1996) 17
7. Davis K.L., Martin E., Turko I.V., and Murad F. Annu. Rev. Pharmacol. Toxicol. 41 (2001) 203
8. Masuda M., Nishino H., and Ohshima H. Chem. Biol. Interact. 139 (2002) 187
9. Haussinger D., and Schliess F. Gut 57 (2008) 1156
10. Rubbo H., DarleyUsmar V., and Freeman B.A. Chem. Res. Toxicol. 9 (1996) 809
11. Stamler J.S., Singel D.J., and Loscalzo J. Science 258 (1992) 1898
12. Sawa T., and Ohshima H. Nitric Oxide 14 (2006) 91
13. Laval F., and Wink D.A. Carcinogenesis 15 (1994) 443
14. Dedon P.C., and Tannenbaum S.R. Arch. Biochem. Biophys. 423 (2004) 12
15. Lakshmi V.M., Hsu F.F., and Zenser T.V. Chem. Res. Toxicol. 18 (2005) 1038
16. Lakshmi V.M., Hsu F.F., Davis B.B., and Zenser T.V. Chem. Res. Toxicol. 14 (2001) 312
17. Zenser T.V., Lakshmi A.M., Hsu F.F., and Davis B.B. Mutat. Res. 506 (2002) 29
18. Lakshmi V.M., Hsu F.F., and Zenser T.V. Chem. Res. Toxicol. 15 (2002) 1059
19. Lakshmi V.M., and Zenser T.V. Life Sci. 80 (2007) 644
20. Nedospasov A.A. J. Biochem. Mol. Toxicol. 16 (2002) 109
21. Challis B.C., and Kyrtopoulos S.A. J. Chem. Soc., Perkin Trans. 1 (1979) 299
22. Challis B.C., and Kyrtopoulos S.A. J. Chem. Soc., Perkin Trans. 2 (1978) 1296
23. Kirsch M., Fuchs A., and de Groot H. J. Biol. Chem. 278 (2003) 11931
24. Wolf T., Niehaus-Rolf C., and Luepke N.P. Food Chem. Toxicol. 41 (2003) 561
25. Mittal G., Brar A.P.S., and Soni G. Exp. Toxicol. Pathol. 59 (2008) 409
26. Dennehy M.K., and Loeppky R.N. Chem. Res. Toxicol. 18 (2005) 556
27. Hecht S.S. Chem. Res. Toxicol. 11 (1998) 559
28. Lin H.L., and Hollenberg P.F. Chem. Res. Toxicol. 14 (2001) 562
29. Goto Y., Matsuda T., Ito K., Huh H.H., Thomale J., Rajewsky M.F., Hayatsu H., and Negishi T. Mutat. Res. 425 (1999) 125
30. Anderson L.M., Souliotis V.L., Chhabra S.K., Moskal T.J., Harbaugh S.D., and Kyrtopoulos S.A. Int. J. Cancer 66 (1996) 130
31. Magee P.N., and Hultin T. Biochem. J. 83 (1962) 106
32. Mizgireuv I.V., Majorova I.G., Gorodinskaya V.M., Khudoley V.V., and Revskoy S.Y. Toxicol. Pathol. 32 (2004) 514
33. Fukushima S., Wanibuchi H., Morimura K., Nakae D., Tsuda H., Imaida K., Shirai T., Tatematsu M., Tsukamoto T., Hirose M., and Furukawa F. Cancer Lett. 222 (2005) 11
34. Tanaka A., Hisanaga A., Inamasu T., Hirata M., and Ishinishi N. Food Chem. Toxicol. 26 (1988) 847
35. Anderson L.M., Carter J.P., Logsdon D.L., Driver C.L., and Kovatch R.M. Carcinogenesis 13 (1992) 2107
36. http://www.epa.gov/iris/subst/0045.htm.
37. Hawkins M., and Downs A.J. J. Phys. Chem. 88 (1984) 1527
38. Wang X.F., Zheng Q.K., and Fan K.N. J. Mol. Struct. 403 (1997) 245
39. Wang X.F., and Qin Q.Z. Spectrochim. Acta Part A 54 (1998) 575
40. Lee C.L., Lee Y.P., Wang X.F., and Qin Q.Z. J. Chem. Phys. 109 (1998) 10446
41. Wang X., and Qin Q.Z. J. Photochem. Photobiol. A: Chem. 122 (1999) 1
42. Bibart C.H., and Ewing G.E. J. Chem. Phys. 61 (1974) 1293
43. Bradley G.M., Siddall W., Strauss H.L., and Varetti E.L. J. Phys. Chem. 79 (1975) 1949
44. Georges R., Lievin J., Herman M., and Perrin A. Chem. Phys. Lett. 256 (1996) 675
45. Harcourt R.D., and Wolynec P.P. J. Phys. Chem. A 104 (2000) 2138
46. Halpern A.M., and Glendening E.D. J. Chem. Phys. 126 (2007) 154305
47. Glendening E.D., and Halpern A.M. J. Chem. Phys. 127 (2007) 164307
48. Demaison J., Herman M., Lievin J., Margules L., and Mollendal H. J. Mol. Spectrosc. 244 (2007) 160
49. Fateley W.G., Bent H.A., and Crawford J.B. J. Chem. Phys. 31 (1959) 204
50. Hisatsune I.C., Devlin J.P., and Wada Y. J. Chem. Phys. 33 (1960) 714
51. Varetti E.L., and Pimentel G.C. J. Chem. Phys. 55 (1971) 3813
52. Nour E.M., Chen L.H., and Laane J. J. Phys. Chem. 87 (1983) 1113
53. Holland R.F., Maier W.B., and Ii J. Chem. Phys. 78 (1983) 2928
54. Stirling A., Papai I., Mink J., and Salahub D.R. J. Chem. Phys. 100 (1994) 2910
55. Vladimiroff T. J. Mol. Struct. (Theochem) 342 (1995) 103
56. Jubert A.H., Varetti E.L., Villar H.O., and Castro E.A. Theor. Chim. Acta 64 (1984) 313
57. Marletta M.A. J. Biol. Chem. 268 (1993) 12231
58. Marletta M.A. Cell 78 (1994) 927
59. Morgon N.H., De Souza A.R., and Sambrano J.R. J. Mol. Struct. (Theochem) 759 (2006) 189
60. Lv C.L., Liu Y.D., Wang Y.H., and Zhong R.G. Acta Chim. Sinica 65 (2007) 1568
61. Mirvish S.S. Toxicol. Appl. Pharmacol. 31 (1975) 325
62. Becke A.D. J. Chem. Phys. 98 (1993) 5648
63. Lee C.T., Yang W.T., and Parr R.G. Phys. Rev. B 37 (1988) 785
64. Frisch M.J., Pople J.A., and Binkley J.S. J. Chem. Phys. 80 (1984) 3265
65. Gonzalez C., and Schlegel H.B. J. Phys. Chem. 94 (1990) 5523
66. Noga J., and Bartlett R.J. J. Chem. Phys. 86 (1987) 7041
67. Tomasi J., and Persico M. Chem. Rev. 94 (1994) 2027
68. Villamena F.A., Xia S.J., Merle J.K., Lauricella R., Tuccio B., Hadad C.M., and Zweier J.L. J. Am. Chem. Soc. 129 (2007) 8177
69. Villamena F.A., Merle J.K., Hadad C.M., and Zweier J.L. J. Phys. Chem. A 111 (2007) 9995
70. Lv C.L., Liu Y.D., and Zhong R.G. J. Phys. Chem. A 113 (2009) 713
71. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.A. Montgomery, Jr., R.E. Stratmann, J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, D.K. Malick, A.D. Rabuck, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. AlLaham, C.Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chem, M.W. Wong, J.L. Andres, C. Gonzalez, M. Head-Gordon, E.S. Replogle, J.A. Pople, Gaussian 03, Revison B.05, Gaussian Inc., Pittsburgh, PA, 1998.
72. Pimentel A.S., Lima F.C.A., and Silva A.B.F. J. Phys. Chem. A 111 (2007) 2913
73. Lv C.L., Liu Y.D., and Zhong R.G. J. Phys. Chem. A 112 (2008) 7098
74. Liu Y.D., and Zhong R.G. J. Mol. Struct. (Theochem) 765 (2006) 143
75. Hutschka F., Dedieu A., Eichberger M., Fornika R., and Leitner W. J. Am. Chem. Soc. 119 (1997) 4432
76. Ignatyev I.S., and Schaefer III H.F. J. Am. Chem. Soc. 119 (1997) 12306
77. Maranzana A., Ghigo G., Tonachini G., and Barker J.R. J. Phys. Chem. A 112 (2008) 3656