A method to calculate the one-electron reduction potentials for nitroaromatic compounds based on gas-phase quantum mechanics

Journal of Computational Chemistry

Volumn 32, Issue 2, 2011, Pages 226-239

  Phillips, Kathy L ^a   Sandler, Stanley I ^a   Chiu, Pei C ^b  

^a University of Delaware   (United States)

^b DUPONT COMPANY   (United States)

Author keywords

electron affinity; nitroaromatic compounds; one electron reduction potential; quantum mechanics; solvation

Indexed keywords

ADIABATIC ELECTRON AFFINITY; DENSITY-FUNCTIONAL CALCULATIONS; EMPIRICAL CORRELATIONS; ENVIRONMENTAL CONTAMINANT; ENVIRONMENTAL FATE; GASPHASE; LINEAR CORRELATION; MEAN ABSOLUTE DEVIATIONS; NITROAROMATIC COMPOUND; ONE-ELECTRON REDUCTION POTENTIALS; PHASE CALCULATION; QUANTUM MECHANICS;

AROMATIC COMPOUNDS; ELECTRONS; ERRORS; FORECASTING; MECHANICS; QUANTUM THEORY; SOLVATION; SYSTEMATIC ERRORS;

ELECTRON AFFINITY;

AROMATIC HYDROCARBON; NITRO DERIVATIVE;

ARTICLE; CHEMISTRY; ELECTRON; GAS; OXIDATION REDUCTION REACTION; QUANTUM THEORY; THERMODYNAMICS;

ELECTRONS; GASES; HYDROCARBONS, AROMATIC; NITRO COMPOUNDS; OXIDATION-REDUCTION; QUANTUM THEORY; THERMODYNAMICS;

EID: 77957350575     PISSN: 01928651     EISSN: 1096987X     Source Type: Journal    
DOI: 10.1002/jcc.21608     Document Type: Article

References (95)

1. Nishino, S. F., Spain, J. C., He, Z., In Biodegradation of Nitroaromatic Compounds and Explosives;, Spain, J. C., Hughes, J. B., Knackmuss, H., Eds.; CRC Press LLC: Boca Raton, FL, 2000; p. 7-61.
2. Tokiwa, H., Ohnishi, Y., CRC Crit Rev Toxicol 1986, 17, 23.
3. Anderson, K. E., Hammons, G. J., Kadlubar, F. F., Potter, J. D., Kaderlik, K. R., Ilett, K. F., Minchin, R. F., Teitel, C. H., Chou, H. C., Martin, M. V., Guengerich, F. P., Barone, G. W., Lang, N. P., Peterson, L. A., Carcinogenesis 1997, 18, 1085.
4. Winget, P., Cramer, C. J., Truhlar, D. G., Theor Chem Acc 2004, 112, 217-227.
5. Trasatti, S., Pure Appl Chem 1986, 58, 955.
6. Lewis, A., Bumpus, J. A., Truhlar, D. G., Cramer, C. J., J Chem Educ 2004, 81, 596.
7. Lewis, A., Bumpus, J. A., Truhlar, D. G., Cramer, C. J., J Chem Educ 2007, 84, 934.
8. Hofstetter, T. B., Heijman, C. G., Haderlein, S. B., Holliger, C., Schwarzenbach, R. P., Environ Sci Technol 1999, 33, 1479.
9. Clarke, E. D., Wardman, P., Goulding, K. H., Biochem Pharmacol 1980, 29, 2684.
10. Schwarzenbach, R. P., Stierli, R., Lanz, K., Zeyer, J., Environ Sci Technol 1990, 24, 1566.
11. Dunnivant, F. M., Schwarzenbach, R. P., Macalady, D. L., Environ Sci Technol 1992, 26, 2133.
12. Klausen, J., Trober, S. P., Haderlein, S. B., Schwarzenbach, R. P., Environ Sci Technol 1995, 29, 2396.
13. Naka, D., Kim, D., Strathmann, T. J., Environ Sci Technol 2006, 40, 3006.
14. Naka, D., Kim, D., Carbonaro, R. F., Strathmann, T. J., Environ Toxicol Chem 2008, 27, 1257.
15. Adams, G. E., Clarke, E. D., Jacobs, R. S., Stratford, I. J., Wallace, R. G., Wardman, P., Watts, M. E., Biochem Biophys Res Commun 1976, 72, 824.
16. Winget, P., Weber, E. J., Cramer, C. J., Truhlar, D. G., Phys Chem Chem Phys 2000, 2, 1231.
17. Namazian, M., Almodarresieh, H. A., Noorbala, M. R., Zare, H. R., Chem Phys Lett 2004, 396, 424.
18. Namazian, M., Zare, H. R., Biophys Chem 2005, 117, 13.
19. Zubatyuk, R. I., Gorb, L., Shishkin, O. V., Qasim, M., Leszczynski, J., J Comput Chem 2010, 31, 144.
20. Cramer, C. J., Essentials of Computational Chemistry; Wiley: Chichester, England, 2004.
21. Wheeler, R. A., J Am Chem Soc 1994, 116, 11048.
22. Bartmess, J. E., J Phys Chem 1994, 98, 6420.
23. Meisel, D., Neta, P., J Am Chem Soc 1975, 97, 5198.
24. Riefler, R. G., Smets, B. F., Environ Sci Technol 2000, 34, 3900.
25. Wardman, P., J Phys Chem Ref Data 1989, 18, 1637.
26. Rienstra-Kiracofe, J. C., Tschumper, G. S., Schaefer, H. F., Nandi, S., Ellison, G. B., Chem Rev 2002, 102, 231.
27. Zlatkis, A., Lee, C. K., Wentworth, W. E., Chen, E. C. M., Anal Chem 1983, 55, 1596.
28. Fukuda, E. K., McIver, R. T., J Am Chem Soc 1985, 107, 2291.
29. Grimsrud, E. P., Caldwell, G., Chowdhury, S., Kebarle, P., J Am Chem Soc 1985, 107, 4627.
30. Chowdhury, S., Heinis, T., Grimsrud, E. P., Kebarle, P., J Phys Chem 1986, 90, 2747.
31. Chowdhury, S., Grimsrud, E. P., Heinis, T., Kebarle, P., J Am Chem Soc 1986, 108, 3630.
32. Chowdhury, S., Kishi, H., Dillow, G. W., Kebarle, P., Can J Chem 1989, 67, 603.
33. Chen, E. C. M., Chen, E. S., Milligan, M. S., Wentworth, W. E., Wiley, J. R., J Phys Chem 1992, 96, 2385.
34. Chen, E. C. M., Wiley, J. R., Batten, C. F., Wentworth, W. E., J Phys Chem 1994, 98, 88.
35. Mishima, M., Huh, C., Lee, H. W., Nakamura, H., Fujio, M., Tsuno, Y., Tetrahedron Lett 1995, 36, 2265.
36. Huh, C., Kang, C. H., Lee, H. W., Nakamura, H., Mishima, M., Tsuno, Y., Yamataka, H., Bull Chem Soc Jpn 1999, 72, 1083.
37. Desfrancois, C., Periquet, V., Lyapustina, S. A., Lippa, T. P., Robinson, D. W., Bowen, K. H., Nonaka, H., Compton, R. N., J Chem Phys 1999, 111, 4569.
38. Zhao, Y., Truhlar, D. G., J Phys Chem A 2004, 108, 6908.
39. Becke, A. D., J Chem Phys 1997, 107, 8554.
40. Schmider, H. L., Becke, A. D., J Chem Phys 1998, 108, 9624.
41. Lynch, B. J., Zhao, Y., Truhlar, D. G., J Phys Chem A 2003, 107, 1384.
42. Schäfer, A., Huber, C., Ahlrichs, R., J Chem Phys 1994, 100, 5829.
43. Fu, Y., Liu, L., Yu, H. Z., Wang, Y. M., Guo, Q. X., J Am Chem Soc 2005, 127, 7227.
44. Curtiss, L. A., Redfern, P. C., Raghavachari, K., Pople, J. A., J Chem Phys 1998, 109, 42.
45. Curtiss, L. A., Raghavachari, K., Redfern, P. C., Rassolov, V., Pople, J. A., J Chem Phys 1998, 109, 7764.
46. Baboul, A. G., Curtiss, L. A., Redfern, P. C., Raghavachari, K., J Chem Phys 1999, 110, 7650.
47. Curtiss, L. A., Raghavachari, K., Redfern, P. C., Pople, J. A., J Chem Phys 2000, 112, 7374.
48. Evans, D. H., Chem Rev 2008, 108, 2113.
49. Cossi, M., Scalmani, G., Rega, N., Barone, V., J Chem Phys 2002, 117, 43.
50. Cammi, R., Mennucci, B., Tomasi, J., J Phys Chem A 1999, 103, 9100.
51. Barone, V., Cossi, M., Tomasi, J., J Comput Chem 1998, 19, 404.
52. Barone, V., Cossi, M., Tomasi, J., J Chem Phys 1997, 107, 3210.
53. Cossi, M., Barone, V., Cammi, R., Tomasi, J., Chem Phys Lett 1996, 255, 327.
54. Miertus, S., Scrocco, E., Tomasi, J., Chem Phys 1981, 55, 117.
55. Miertus, S., Tomasi, J., Chem Phys 1982, 65, 239.
56. CancÃs, E., Mennucci, B., Tomasi, J., J Chem Phys 1997, 107, 3032.
57. Cossi, M., Barone, V., Mennucci, B., Tomasi, J., Chem Phys Lett 1998, 286, 253.
58. Barone, V., Cossi, M., J Phys Chem A 1998, 102, 1995.
59. Mennucci, B., Tomasi, J., J Chem Phys 1997, 106, 5151.
60. Mennucci, B., CancÃs, E., Tomasi, J., J Phys Chem B 1997, 101, 10506.
61. Tomasi, J., Mennucci, B., Cances, E., J Mol Struct-Theochem 1999, 464, 211.
62. Cossi, M., Barone, V., Robb, M. A., J Chem Phys 1999, 111, 5295.
63. Cammi, R., Mennucci, B., Tomasi, J., J Phys Chem A 2000, 104, 5631.
64. Cossi, M., Barone, V., J Chem Phys 2000, 112, 2427.
65. Cossi, M., Barone, V., J Chem Phys 2001, 115, 4708.
66. Cossi, M., Rega, N., Scalmani, G., Barone, V., J Chem Phys 2001, 114, 5691.
67. Cossi, M., Rega, N., Scalmani, G., Barone, V., J Comput Chem 2003, 24, 669.
68. Tomasi, J., Mennucci, B., CancÃs, E,. J Mol Struct THEOCHEM 1999, 464, 211.
69. Kelly, C. P., Cramer, C. J., Truhlar, D. G., J Chem Theory Comput 2005, 1, 1133.
70. Marenich, A. V., Olson, R. M., Kelly, C. P., Cramer, C. J., Truhlar, D. G., J Chem Theory Comput 2007, 3, 2011.
71. Chamberlin, A. C., Cramer, C. J., Truhlar, D. G., J Phys Chem B 2008, 112, 8651.
72. Hammett, L. P., Chem Rev 1935, 17, 125.
73. Johnson, C. D., The Hammett Equation; Cambridge University Press: London, 1973.
74. Sjöberg, L., Eriksen, T. E., J Chem Soc Faraday Trans 1980, 76, 1402.
75. Koopmans, T., Physica 1934, 1, 104.
76. Hehre, W. J., Radom, P. V., Schleyer, R., Pople, J. A., Ab Initio Molecular Orbital Theory; Wiley: New York, 1986.
77. Becke, A. D., J Chem Phys 1993, 98, 5648.
78. Hehre, W. J., Ditchfield, R., Pople, J. A., J Chem Phys 1972, 56, 2257.
79. University of Minnesota Computational Chemistry Group. MG3S basis set: Downloaded from, 2009.
80. Pople, J. A., Nesbet, R. K., J Chem Phys 1954, 22, 571.
81. Easton, R. E., Giesen, D. J., Welch, A., Cramer, C. J., Truhlar, D. G., Theor Chim Acta 1996, 93, 281.
82. Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Montgomery, J. A., Jr., Vreven, T., Kudin, K. N., Burant, J. C., Millam, J. M., Iyengar, S. S., Tomasi, J., Barone, V., Mennucci, B., Cossi, M., Scalmani, G., Rega, N., Petersson, G. A., Nakatsuji, H., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Klene, M., Li, X., Knox, J. E., Hratchian, H. P., Cross, J. B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R. E., Yazyev, O., Austin, A. J., Cammi, R., Pomelli, C., Ochterski, J. W., Ayala, P. Y., Morokuma, K., Voth, G. A., Salvador, P., Dannenberg, J. J., Zakrzewski, V. G., Dapprich, S., Daniels, A. D., Strain, M. C., Farkas, O., Malick, D. K., Rabuck, A. D., Raghavachari, K., Foresman, J. B., Ortiz, J. V., Cui, Q., Baboul, A. G., Clifford, S., Cioslowski, J., Stefanov, B. B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Martin, R. L., Fox, D. J., Keith, T., Al-Laham, M. A., Peng, C. Y., Nanayakkara, A., Challacombe, M., Gill, P. M. W., Johnson, B., Chen, W., Wong, M. W., Gonzalez, C., Pople, J. A., Gaussian 03, revision B.05. Gaussian, Inc.: Wallingford, CT, 2004.
83. Thompson, J. D., Kelly, C. P., Lynch, B. J., Xidos, J. D., Li, J., Hawkins, G. D., Zhu, T., Volobuev, Y., Dupuis, M., Rinaldi, D., Liotard, D. A., Cramer, C. J., Truhlar, D. G., SMXGAUSS, version 3.3. University of Minnesota: Minneapolis, 2006.
84. Chamberlin, A. C., Kelly, C. P., Pu, J., Thompson, D. J., Xidos, J. D., Li, J., Zhu, T., Hawkins, G. D., Chuang, Y.-Y., Fast, P. L., Lynch, B. J., Liotard, D. A., Rinaldi, D., Gao, J., Cramer, C. J., Truhlar, D. G., GAMESSPLUS, version 4.8. University of Minnesota: Minneapolis, MN, 2007.
85. Mikhailov, M. N., Mendkovich, A. S., Kuz'minskii, M. B., Kapranov, V. A., Rusakov, A. I., Russ Chem Bull 2005, 54, 2735.
86. Mikhailov, M. N., Mendkovich, A. S., Kuminsky, M. B., Rusakov, A. I., J Mol Struct-Theochem 2007, 847, 103.
87. Iwatsuki, S., Inukai, K. I., J Polym Sci Part A: Polym Chem 1974, 12, 1437.
88. Nakamura, H., Xidos, J. D., Chamberlin, A. C., Kelly, C. P., Valero, R., Thompson, J. D., Li, J., Hawkins, G. D., Zhu, T., Lynch, B. J., Volobuev, Y., Rinaldi, D., Liotard, D. A., Cramer, C. J., Truhlar, D. G., HONDOPLUS, version 5.1 (based on HONDO v.99.6). University of Minnesota, Minneapolis, 2007.
89. Dupuis, M., Marquez, A., Davidson, E. R., Quantum Chemistry Program Exchange (QCPE); Indiana University: Bloomington, IN, 1999.
90. U.S. Environmental Protection Agency. Air and steam stripping of toxic pollutants. Technical Report EPA-68-03-002, Industrial Environmental Research Laboratory, Cincinnati, OH, 1982.
91. Hine, J., Mookerjee, P. K., J Org Chem 1975, 40, 292.
92. Schüürmann, G., J Comput Chem 2000, 21, 17.
93. Montgomery, J. H., Groundwater Chemicals Desk Reference; CRC Press: Florida, 1996.
94. U.S. National Library of Medicine. Hazardous Substances Data Bank; National Institutes of Health: USA. Available at:, at:http://toxnet.nlm.nih.gov/ cgi-bin/sis/htmlgen?HSDB Accessed online Jan 2010.
95. de Abreu, F. C., de Paula, F. S., dos Santos, A. F., Sant'Ana, A. E. G., de Almeida, M. V., Cesar, E. T., Trindade, M. N., Goulart, M. O. F., Biorg Med Chem 2001, 9, 659.