Abiotic reduction of nitroaromatic contaminants by iron(II) complexes with organothiol ligands

Environmental Toxicology and Chemistry

Volumn 27, Issue 6, 2008, Pages 1257-1266

  Naka, Daisuke ^a   Kim, Dongwook ^a   Carbonaro, Richard F ^b   Strathmann, Timothy J ^a  

^a University of Illinois at Urbana Champaign   (United States)

^b MANHATTAN COLLEGE   (United States)

Author keywords

Abiotic reduction; Ferrous iron; Natural attenuation; Nitroaromatic; Thiol

Indexed keywords

AROMATIC COMPOUNDS; IRON COMPOUNDS;

ABIOTIC REDUCTION; IRON(II) COMPLEXES;

IRON;

ANILINE DERIVATIVE; AROMATIC NITRO COMPOUND; CYSTEINE; IRON COMPLEX; LIGAND; METAL; REDUCING AGENT; THIOGLYCOLIC ACID; THIOL DERIVATIVE;

CHEMICAL POLLUTANT; COMPLEXATION; EXPERIMENTAL STUDY; LIGAND; NITROGEN; REDOX POTENTIAL; REDUCTION; SPECIATION (CHEMISTRY);

ACCURACY; ARTICLE; CHEMICAL COMPOSITION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; COMPLEX FORMATION; MEASUREMENT; OXIDATION REDUCTION POTENTIAL; OXIDATION REDUCTION REACTION; PRIORITY JOURNAL; REDUCTION;

ELECTRONS; IRON; KINETICS; LIGANDS; MOLECULAR STRUCTURE; NITROGEN COMPOUNDS; ORGANIC CHEMICALS; OXIDATION-REDUCTION; SULFHYDRYL COMPOUNDS;

KOBUS;

EID: 45249124949     PISSN: 07307268     EISSN: None     Source Type: Journal    
DOI: 10.1897/07-505.1     Document Type: Article

References (40)

1. Stone AT, Godtfredsen KL, Deng B. 1994. Sources and reactivity of reductants encountered in aquatic environments. In Bidoglio G, Stumm W, eds, Chemistry of Aquatic Systems: Local and Global Perspectives. Kluwer, Dordrecht, The Netherlands, pp 337-374.
2. Lovley DR, Holmes DE, Nevin KP. 2004. Dissimilatory Fe(III) and Mn(IV) reduction. Adv Microb Physiol 49:219-286.
3. 2S to sedimentary organic matter. Nature 329:623-625.
4. Schwarzenbach RP, Gschwend PM, Imboden DM. 2003. Environmental Organic Chemistry, 2nd ed. Wiley Interscience, Hoboken, NJ, USA.
5. McCormick ML, Adriaens P. 2004. Carbon tetrachloride transformation on the surface of nanoscale biogenic magnetite particles. Environ Sci Technol 38:1045-1053.
6. Williams AGB, Gregory KB, Parkin GF, Scherer MM. 2005. Hexahydro-1,3,5-trinitro-1,3,5-triazine transformation by biologically reduced ferrihydrite: Evolution of Fe mineralogy, surface area, and reaction rates. Environ Sci Technol 39:5183-5189.
7. Klausen J, Tröber SP, Haderlein SB, Schwarzenbach RP. 1995. Reduction of substituted nitrobenzenes by Fe(II) in aqueous mineral suspensions. Environ Sci Technol 29:2396-2404.
8. Elsner M, Schwarzenbach RP, Haderlein SB. 2004. Reactivity of Fe(II)-bearing minerals toward reductive transformation of organic contaminants. Environ Sci Technol 38:799-807.
9. Hofstetter TB, Schwarzenbach RP, Haderlein SB. 2003. Reactivity of Fe(II) species associated with clay minerals. Environ Sci Technol 37:519-528.
10. Strathmann TJ, Stone AT. 2003. Mineral surface catalysis of reactions between Fe(II) and oxime carbamate pesticides. Geochim Cosmochim Acta 67:2775-2791.
11. II bound to magnetite. Environ Sci Technol 38:1408-1414.
12. Amonette JE, Workman DJ, Kennedy DW, Fruchter JS, Gorby YA. 2000. Dechlorination of carbon tetrachloride by Fe(II) associated with goethite. Environ Sci Technol 34:4606-4613.
13. 0 species as major reductant. Chemical Geology 151:85-93.
14. Chun CL, Hozalski RM, Arnold WA. 2007. Degradation of disinfection by-products by carbonate green rust. Environ Sci Technol 41:1615-1621.
15. Klupinski TP, Chin YP, Traina SJ. 2004. Abiotic degradation of pentachloronitrobenzene by Fe(II): Reactions on goethite and iron oxide nanoparticles. Environ Sci Technol 38:4353-4360.
16. Perlinger JA, Buschmann J, Angst W, Schwarzenbach RP. 1998. Iron porphyrin and mercaptojuglone mediated reduction of polyhalogenated methanes and ethanes in homogeneous aqueous solution. Environ Sci Technol 32:2431-2437.
17. Schwarzenbach RP, Stierli R, Lanz K, Zeyer J. 1990. Quinone and iron porphyrin mediated reduction of nitroaromatic compounds in homogeneous aqueous solution. Environ Sci Technol 24:1566-1574.
18. Kwon MJ, Finneran KT. 2006. Microbially mediated biodegradation of hexahydro-1,3,5-trinitro-1,3,5-triazine by extracellular electron shuttling compounds. Appl Environ Microbiol 72:5933-5941.
19. Dunnivant FM, Schwarzenbach RP, Macalady DL. 1992. Reduction of substituted nitrobenzenes in aqueous solutions containing natural organic matter. Environ Sci Technol 26:2133-2141.
20. Curtis GP, Reinhard M. 1994. Reductive dehalogenation of hexachloroethane, carbon tetrachloride, and bromoform by anthraquinone disulfonate and humic acid. Environ Sci Technol 28: 2393-2401.
21. II: Influence of organic ligands and natural organic matter. Environ Sci Technol 36:5172-5183.
22. Naka D, Kim D, Strathmann TJ. 2006. Reduction of nitroaromatic contaminants by aqueous iron(II)-catechol complexes. Environ Sci Technol 40:3006-3012.
23. Kim D, Strathmann TJ. 2007. Role of organically complexed iron(II) species in the reductive transformation of RDX in anoxic environments. Environ Sci Technol 41:1257-1264.
24. Bussan AL, Strathmann TJ. 2007. Influence of organic ligands on the reduction of polyhalogenated alkanes by iron(II). Environ Sci Technol 41:6740-6747.
25. Mathews CK, van Holde KE. 1996. Biochemistry, 2nd ed. Benjamin Cummings, Menlo Park, CA, USA.
26. Perlinger JA, Kalluri VM, Venkatapathy R, Angst W. 2002. Addition of hydrogen sulfide to juglone. Environ Sci Technol 36: 2663-2669.
27. Ferdelman TG, Church TM, Luther GW. 1991. Sulfur enrichment of humic substances in a Delaware salt marsh sediment core. Geochim Cosmochim Acta 55:979-988.
28. Urban NR, Ernst K, Bernasconi S. 1999. Addition of sulfur to organic matter during early diagenesis of lake sediments. Geochim Cosmochim Acta 63:837-853.
29. Xia K, Weesner F, Bleam WF, Bloom PR, Skyllberg UL, Helmke PA. 1998. XANES studies of oxidation states of sulfur in aquatic and soil humic substances. Soil Sci Soc Am J 62:1240-1246.
30. Struyk Z, Sposito G. 2001. Redox properties of standard humic acids. Geoderma 102:329-346.
31. Nepal JK, Dubey SN. 1988. Equilibrium study of the complex formation of some bivalent transition metal ions with sulfur oxygen donor ligands. Indian J Chem 65:795.
32. Berthon G. 1995. The stability constants of metal complexes of amino acids with polar side chains. Pure Appl Chem 67:1117-1240.
33. Martell AE, Smith RM, Motekaitis RJ. 1997. Critically Selected Stability Constants of Metal Complexes Database, Ver 4.0. U.S. Department of Commerce, National Institute of Standards and Technology, Gaithersburg, MD.
34. Martell AE, Hancock RD. 1996. Metal Complexes in Aqueous Solutions. Plenum, New York, NY, USA.
35. Eigen M. 1963. Fast elementary steps in chemical reaction mechanisms. Pure Appl Chem 6:97-115.
36. Buerge IJ, Hug SJ. 1998. Influence of organic ligands on chromium(VI) reduction by iron(II). Environ Sci Technol 32:2092-2099.
37. King DW. 1998. Role of carbonate speciation on the oxidation rate of Fe(II) in aquatic systems. Environ Sci Technol 32:2997-3003.
38. Jameson RF, Linert W. 1991. Complex formation followed by internal electron transfer: The reaction between cysteine and iron(III). Monatsh Chem 122:887-906.
39. Hartenbach A, Hofstetter TB, Berg M, Bolotin J, Schwarzenbach RP. 2006. Using nitrogen isotope fractionation to assess abiotic reduction of nitroaromatic compounds. Environ Sci Technol 40: 7710-7716.
40. Amirbahman A, Sigg L, von Gunten U. 1997. Reductive dissolution of Fe(III) (hydr)oxides by cysteine: Kinetics and mechanism. J Colloid Interface Sci 194:194-206.