Reduction rate constants for nitroaromatic compounds estimated from adiabatic electron affinities

Environmental Science and Technology

Volumn 44, Issue 19, 2010, Pages 7431-7436

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

^a UNIVERSITY OF DELAWARE   (United States)

^b DUPONT COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADIABATIC ELECTRON AFFINITY; ENVIRONMENTAL CONTAMINANT; ENVIRONMENTAL FATE; FE COMPLEXES; HALF LIVES; K-VALUES; LINEAR CORRELATION; LINEAR FREE ENERGY RELATIONSHIPS; NATURAL ORGANIC MATTERS; NITROAROMATIC COMPOUND; ONE-ELECTRON REDUCTION POTENTIALS; ORDER OF MAGNITUDE; QUANTUM MECHANICS; REDUCING SYSTEMS; REDUCTION RATE;

AROMATIC COMPOUNDS; BIOLOGICAL MATERIALS; IMPURITIES; NITROBENZENE; QUANTUM THEORY;

RATE CONSTANTS;

AROMATIC NITRO COMPOUND; IRON COMPLEX; NATURAL ORGANIC MATTER; NITROBENZENE; QUINONE DERIVATIVE;

ADIABATIC PROCESS; ELECTRON; ENVIRONMENTAL FATE; IRON; ORGANIC MATTER; REDUCTION;

ADIABATICITY; ARTICLE; CHEMICAL REACTION; CORRELATIONAL STUDY; ELECTRON; QUANTUM MECHANICS; REDUCTION;

CYCLIZATION; ELECTRONS; KINETICS; NITROGEN COMPOUNDS; OXIDATION-REDUCTION; THERMODYNAMICS;

EID: 77957354603     PISSN: 0013936X     EISSN: 15205851     Source Type: Journal    
DOI: 10.1021/es100142v     Document Type: Article

References (28)

1. Nishino, S. F.; Spain, J. C.; He, Z. Strategies for aerobic degradation of nitroaromatic compounds by bacteria: process discovery to field application. In Biodegradation of Nitroaromatic Compounds and Explosives; Spain, J. C., Hughes, J. B., Knackmuss, H., Eds.; CRC Press LLC: Boca Raton, FL, 2000; pp 7 - 61.
2. Tokiwa, H.; Ohnishi, Y. Mutagenicity and carcinogenicity of nitroarenes and their sources in the environment CRC Crit. Rev. Toxicol. 1986, 17, 23-60
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. Metabolic activation of aromatic amines by human pancreas Carcinogenesis 1997, 18, 1085-1092
4. Rickert, D. E. Toxicity of Nitroaromatic Compounds; Hemisphere Publishing Corp.: Bristol, PA, 1984.
5. Hofstetter, T. B.; Heijman, C. G.; Haderlein, S. B.; Holliger, C.; Schwarzenbach, R. P. Complete reduction of TNT and other (poly)nitroaromatic compounds under iron reducing subsurface conditions Environ. Sci. Technol. 1999, 33, 1479-1487
6. Clarke, E. D.; Wardman, P.; Goulding, K. H. Anaerobic reduction of nitroimidazoles by reduced flavin mono-nucleotide and by xanthine-oxidase Biochem. Pharmacol. 1980, 29, 2684-2687
7. Schwarzenbach, R. P.; Stierli, R.; Lanz, K.; Zeyer, J. Quinone and iron porphyrin mediated reduction of nitroaromatic compounds in homogeneous aqueous-solution Environ. Sci. Technol. 1990, 24, 1566-1574
8. Dunnivant, F. M.; Schwarzenbach, R. P.; Macalady, D. L. Reduction of substituted nitrobenzenes in aqueous-solutions containing natural organic-matter Environ. Sci. Technol. 1992, 26, 2133-2141
9. Klausen, J.; Trober, S. P.; Haderlein, S. B.; Schwarzenbach, R. P. Reduction of substituted nitrobenzenes by Fe(II) in aqueous mineral suspensions Environ. Sci. Technol. 1995, 29, 2396-2404
10. Naka, D.; Kim, D.; Strathmann, T. J. Abiotic reduction of nitroaromatic compounds by aqueous iron(II) - Catechol complexes Environ. Sci. Technol. 2006, 40, 3006-3012
11. Naka, D.; Kim, D.; Carbonaro, R. F.; Strathmann, T. J. Abiotic reduction of nitroaromatic contaminants by iron(II) complexes with organothiol ligands Environ. Toxicol. Chem. 2008, 27, 1257-1266
12. Schwarzenbach, R. P.; Gschwend, P. M.; Imboden, D. M. Environmental Organic Chemistry; 2 nd ed.; John Wiley & Sons, Inc.: Hoboken, NJ, 2003.
13. Evans, M. G.; Polanyi, M. Some applications of the transition state method to the calculation of reaction velocities, especially in solution Trans. Faraday Soc. 1935, 31 0875-0893
14. Bell, R. P. The theory of reactions involving proton transfers Proc. R. Soc. London, Ser. A 1936, 154, 414-429
15. Eberson, L. Electron Transfer Reactions in Organic Chemistry; Springer: Berlin, 1987.
16. Haderlein, S. B.; Hofstetter, T. B.; Schwarzenbach, R. P. Subsurface chemistry of nitroaromatic compounds. In Biodegradation of Nitroaromatic Compounds and Explosives; Spain, J. C.; Hughes, J. B.; Knackmuss, H., Eds.; CRC Press LLC: Boca Raton, FL, 2000; pp 311 - 356.
17. Hartenbach, A.; Hofstetter, T. B.; Berg, M.; Bolotin, J.; Schwarzenbach, R. P. Using nitrogen isotope fractionation to assess abiotic reduction of nitroaromatic compounds Environ. Sci. Technol. 2006, 40, 7710-7716
18. Hartenbach, A. E.; Hofstetter, T. B.; Aeschbacher, M.; Sander, M.; Kim, D.; Strathmann, T. J.; Arnold, W. A.; Cramer, C. J.; Schwarzenbach, R. P. Variability of nitrogen isotope fractionation during the reduction of nitroaromatic compounds with dissolved reductants Environ. Sci. Technol. 2008, 42, 8352-8359
19. Phillips, K. L.; Sandler, S. I.; Chiu, P. C. A method to calculate the one-electron reduction potentials for nitroaromatic compounds based on gas-phase quantum mechanics. J. Comput. Chem. 2010, doi: 10.1002/jcc.21608.
20. Bartmess, J. E. Thermodynamics of the electron and the proton J. Phys. Chem. 1994, 98, 6420-6424
21. Curtiss, L. A.; Raghavachari, K.; Redfern, P. C.; Rassolov, V.; Pople, J. A. Gaussian-3 (G3) theory for molecules containing first and second-row atoms J. Chem. Phys. 1998, 109, 7764-7776
22. Baboul, A. G.; Curtiss, L. A.; Redfern, P. C.; Raghavachari, K. Gaussian-3 theory using density functional geometries and zero-point energies J. Chem. Phys. 1999, 110, 7650-7657
23. Becke, A. D. Density-functional thermochemistry. V. Systematic optimization of exchange-correlation functionals J. Chem. Phys. 1997, 107, 8554-8560
24. Schmider, H. L.; Becke, A. D. Optimized density functionals from the extended G2 test set J. Chem. Phys. 1998, 108, 9624-9631
25. Lynch, B. J.; Zhao, Y.; Truhlar, D. G. Effectiveness of diffuse basis functions for calculating relative energies by density functional theory J. Phys. Chem. A 2003, 107, 1384-1388
26. Neta, P.; Meisel, D. Substituent effects on nitroaromatic radical anions in aqueous solution J. Phys. Chem. 1976, 80, 519-524
27. Barrows, S. E.; Cramer, C. J.; Truhlar, D. G.; Elovitz, M. S.; Weber, E. J. Factors controlling regioselectivity in the reduction of polynitroaromatics in aqueous solution Environ. Sci. Technol. 1996, 30, 3028-3038
28. Oh, S. Y.; Chiu, P. C. Graphite- and soot-mediated reduction of 2,4-dinitrotoluene and hexahydro-1,3,5-trinitro-1,3,5-triazine Environ. Sci. Technol. 2009, 43, 6983-6988