Dehalogenation of persistent halogenated organic compounds: A review of computational studies and quantitative structure-property relationships

Chemosphere

Volumn 131, Issue , 2015, Pages 17-33

  Luo, Jin ^a   Hu, Jiwei ^a   Wei, Xionghui ^b   Fu, Liya ^a   Li, Lingyun ^a  

^a GUIZHOU NORMAL UNIVERSITY   (China)

^b PEKING UNIVERSITY   (China)

Author keywords

Dehalogenation; DFT; Molecular parameter; QSPR; Theoretical study

Indexed keywords

COMPUTATION THEORY; DEHALOGENATION; HALOGENATION; ORGANIC COMPOUNDS; REMEDIATION;

HALOGENATED ORGANIC COMPOUNDS; MOLECULAR PARAMETERS; PHYSIO-CHEMICAL PROPERTIES; QSPR; QUANTITATIVE STRUCTURE - PROPERTY RELATIONSHIPS; QUANTITATIVE STRUCTURE-PROPERTY RELATIONSHIP MODELS; STRUCTURAL CHARACTERISTICS; THEORETICAL STUDY;

DENSITY FUNCTIONAL THEORY;

ANION; GRAPHENE; IRON; ORGANOHALOGEN DERIVATIVE; HALOGENATED HYDROCARBON; POLLUTANT;

BIODEGRADATION; COMPUTER SIMULATION; HALOGENATED HYDROCARBON; LITERATURE REVIEW; MOLECULAR ANALYSIS; NUMERICAL MODEL; PHYSICOCHEMICAL PROPERTY; REACTION KINETICS; TECHNOLOGICAL CHANGE; THEORETICAL STUDY;

AB INITIO CALCULATION; ADSORPTION; CHEMICAL STRUCTURE; DEHALOGENATION; DENSITY FUNCTIONAL THEORY; EXCITATION; GEOMETRY; QUANTITATIVE STRUCTURE PROPERTY RELATION; REACTION ANALYSIS; REVIEW; SURFACE PROPERTY; THERMODYNAMICS; CHEMISTRY; ECOSYSTEM RESTORATION; HALOGENATION; KINETICS; POLLUTANT; QUANTITATIVE STRUCTURE ACTIVITY RELATION; THEORETICAL MODEL;

ENVIRONMENTAL POLLUTANTS; ENVIRONMENTAL RESTORATION AND REMEDIATION; HALOGENATION; HYDROCARBONS, HALOGENATED; KINETICS; MODELS, THEORETICAL; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; THERMODYNAMICS;

EID: 84928724759     PISSN: 00456535     EISSN: 18791298     Source Type: Journal    
DOI: 10.1016/j.chemosphere.2015.02.013     Document Type: Review

References (195)

1. Alonso F., Beletskaya I.P., Yus M. Metal-mediated reductive hydrodehalogenation of organic halides. Chem. Rev. 2002, 102:4009-4092.
2. Amaral Mendes J.J. The endocrine disrupters: a major medical challenge. Food Chem. Toxicol. 2002, 40:781-788.
3. Andrieux C.P., Saveant J.M., Su K.B. Kinetics of dissociative electron transfer. Direct and mediated electrochemical reductive cleavage of the carbon-halogen bond. J. Phys. Chem. 1986, 90:3815-3823.
4. Arnold W.A., Ball W.P., Roberts A.L. Polychlorinated ethane reaction with zero-valent zinc: pathways and rate control. J. Contam. Hydrol. 1999, 40:183-200.
5. Arulmozhiraja S., Morita M. Electron affinities and reductive dechlorination of toxic polychlorinated dibenzofurans: a density functional theory study. J. Phys. Chem. A 2004, 108:3499-3508.
6. Arulmozhiraja S., Fujii T., Tokiwa H. Electron affinity for the most toxic 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD): a density functional theory study. J. Phys. Chem. A 2000, 104:7068-7072.
7. Arulmozhiraja S., Fujii T., Morita M. Density functional theory studies on radical ions of selected polychlorinated biphenyls. J. Phys. Chem. A 2002, 106:10590-10595.
8. Ballerstedt H., Kraus A., Lechner U. Reductive dechlorination of 1,2,3,4-tetrachlorodibenzo-p-dioxin and its products by anaerobic mixed cultures from Saale river sediment. Environ. Sci. Technol. 1997, 31:1749-1753.
9. Berkout V.D., Mazurkiewicz P., Deinzer M.L. Electron energy dependence of regioselective chloride ion loss from polychlorodibenzo-p-dioxins. Relationship between resonance electron energies and virtual orbital energies. J. Am. Chem. Soc. 1999, 121:2561-2570.
10. Bertran J., Gallardo I., Moreno M., Saveant J.M. Dissociative electron transfer. Ab initio study of the carbon-halogen bond reductive cleavage in methyl and perfluoromethyl halides. Role of the solvent. J. Am. Chem. Soc. 1992, 114:9576-9583.
11. Bokare V., Jung J.L., Chang Y.Y., Chang Y.S. Reductive dechlorination of octachlorodibenzo-p-dioxin by nanosized zero-valent zinc: modeling of rate kinetics and congener profile. J. Hazard. Mater. 2013, 250-251:397-402.
12. Borisov Y.A., Garrett B.C., Mazunov V.A., Nekrasov Y.S. DFT calculations for the structure and properties of polychlorodibenzo-para-dioxine anion-radicals. J. Struct. Chem. 2005, 46:591-595.
13. Bunge M., Ballerstedt H., Lechner U. Regiospecific dechlorination of spiked tetra- and trichlorodibenzo-p-dioxins by anaerobic bacteria from PCDD/F-contaminated Spittelwasser sediments. Chemosphere 2001, 43:675-681.
14. Bunge M., Adrian L., Kraus A., Opel M., Lorenz W.G., Andreesen J.R., Görisch H., Lechner U. Reductive dehalogenation of chlorinated dioxins by an anaerobic bacterium. Nature 2003, 421:357-360.
15. Burrow P.D., Aflatooni K., Gallup G.A. Dechlorination rate constants on iron and the correlation with electron attachment energies. Environ. Sci. Technol. 2000, 34:3368-3371.
16. Cantón R.F., Scholten D.E., Marsh G., De Jong P.C., Van den Berg M. Inhibition of human placental aromatase activity by hydroxylated polybrominated diphenyl ethers (OH-PBDEs). Toxicol. Appl. Pharm. 2008, 227:68-75.
17. Cervini-Silva J. Linear free-energy relationship analysis of the fate of chlorinated 1- and 2-carbon compounds by redox-manipulated smectite clay minerals. Environ. Toxicol. Chem. 2003, 22:2298-2305.
18. Chang Y.S., Laramee J.A., Deinzer M.L. Regioselective chloride ion loss from chlorine-37 enriched polychlorodibenzofurans by negative ion mass spectrometry. Anal. Chem. 1991, 63:2715-2718.
19. Chantzis A., Very T., Daniel C., Monari A., Assfeld X. Theoretical evidence of photo-induced charge transfer from DNA to intercalated ruthenium(II) organometallic complexes. Chem. Phys. Lett. 2013, 578:133-137.
20. Chaudhry G.R., Chapalamadugu S. Biodegradation of halogenated organic compounds. Microb. Rev. 1991, 55:59-79.
21. Chen J., Quan X., Peijnenburg W.J.G.M., Yang F. Quantitative structure-property relationships (QSPRs) on direct photolysis quantum yields of PCDDs. Chemosphere 2001, 43:235-241.
22. 0. Chemosphere 2001, 42:367-372.
23. Choi J., Choi W., Mhin B.J. Solvent-specific photolytic behavior of octachlorodibenzo-p-dioxin. Environ. Sci. Technol. 2004, 38:2082-2088.
24. Choi M.P., Ho S.K., So B.K., Cai Z., Lau A.K., Wong M.H. PCDD/F and dioxin-like PCB in Hong Kong air in relation to their regional transport in the Pearl River Delta region. Chemosphere 2008, 71:211-218.
25. Chomicz L., Rak J., Storoniak P. Electron-induced elimination of the bromide anion from brominated nucleobases. A computational study. J. Phys. Chem. B 2012, 116:5612-5619.
26. Combellas C., Kanoufi F., Thiébault A. Reduction of polyfluorinated compounds. J. Phys. Chem. B 2003, 107:10894-10905.
27. Cong X., Xue N., Wang S., Li K., Li F. Reductive dechlorination of organochlorine pesticides in soils from an abandoned manufacturing facility by zero-valent iron. Sci. Total Environ. 2010, 408:3418-3423.
28. Cozza C.L., Woods S.L. Reductive dechlorination pathways for substituted benzenes: a correlation with electronic properties. Biodegradation 1991, 2:265-278.
29. Cwiertny D.M., Arnold W.A., Kohn T., Rodenburg L.A., Roberts A.L. Reactivity of alkyl polyhalides toward granular iron: development of QSARs and reactivity cross correlations for reductive dehalogenation. Environ. Sci. Technol. 2010, 44:7928-7936.
30. Dai Y., Yang D., Zhu F., Wu L., Yang X., Li J. The QSPR (quantitative structure-property relationship) study about the anaerobic biodegradation of chlorophenols. Chemosphere 2006, 65:2427-2433.
31. Darnerud P.O., Eriksen G.S., Jóhannesson T., Larsen P.B., Viluksela M. Polybrominated diphenyl ethers: occurrence, dietary exposure, and toxicology. Environ. Health Persp. 2001, 109:49-68.
32. Ding G., Peijnenburg W.J. Physicochemical properties and aquatic toxicity of poly-and perfluorinated compounds. Crit. Rev. Environ. Sci. Technol. 2013, 43:598-678.
33. Ding N., Chen X., Wu C.L. Interactions between polybrominated diphenyl ethers and graphene surface: a DFT and MD investigation. Environ. Sci. Nano 2014, 1:55-63.
34. Dolfing J., Harrison B.K. The Gibbs free energy of formation of halogenated aromatic compounds and their potential role as electron acceptors in anaerobic environments. Environ. Sci. Technol. 1992, 26:2213-2218.
35. Du Q.S., Huang R.B., Chou K.C. Recent advances in QSAR and their applications in predicting the activities of chemical molecules, peptides and proteins for drug design. Curr. Protein Pept. Sci. 2008, 9:248-259.
36. Eberson L. Electron transfer reactions in organic chemistry. II. An analysis of alkyl halide reduction by electron transfer reagents on the basis of the Marcus theory. Acta. Chem. Scand. B 1982, 36:533-543.
37. Eberson L. Electron transfer reactions in organic chemistry. Reactivity and Structure Concepts in Organic Chemistry 1987, vol. 25:1-234. Springer, Berlin.
38. Eloranta J., Hu J., Suontamo R., Kolehmainen E., Knuutinen J. Ab initio study of halogenated diphenyl ethers. NMR chemical shift prediction. Mag. Res. Chem. 2000, 38:987-993.
39. Enell M., Wennberg L. Distribution of halogenated organic compounds (AOX). Swedish transport to surrounding sea areas and mass balance studies in five drainage systems. Water Sci. Technol. 1991, 24:385-395.
40. Eriksson J., Green N., Marsh G., Bergman Å. Photochemical decomposition of 15 polybrominated diphenyl ether congeners in methanol/water. Environ. Sci. Technol. 2004, 38:3119-3125.
41. Fang L., Zheng M., Xiao K., Yang Y. Tissue-dependent distribution and bioaccumulation of polychlorinated dibenzo-p-dioxins and dibenzofurans in vegetation samples collected from Dongting Lake, China. Environ. Toxicol. Chem. 2008, 27:49-56.
42. Fang L., Huang J., Yu G., Li X. Quantitative structure-property relationship studies for direct photolysis rate constants and quantum yields of polybrominated diphenyl ethers in hexane and methanol. Ecotox. Environ. Safe. 2009, 72:1587-1593.
43. Farrar N.J., Smith K.E.C., Lee R.G.M., Thomas G.O., Sweetman A.J., Jones K.C. Atmospheric emissions of polybrominated diphenyl ethers and other persistent organic pollutants during a major anthropogenic combustion event. Environ. Sci. Technol. 2004, 38:1681-1685.
44. Fedurco M., Jorand Sartoretti C., Augustynski J. Reductive cleavage of the carbon-halogen bond in simple methyl and methylene halides. Reactions of the methyl radical and carbene at the polarized electrode/aqueous solution interface. Langmuir 2001, 17:2380-2387.
45. Fetzner S. Bacterial dehalogenation. Appl. Microb. Biotechnol. 1998, 50:633-657.
46. Fonseca Guerra C., Handgraaf J.W., Baerends E.J., Bickelhaupt F.M. Voronoi deformation density (VDD) charges: assessment of the Mulliken, Bader, Hirshfeld, Weinhold, and VDD methods for charge analysis. J. Comput. Chem. 2004, 25:189-210.
47. Freeman P.K., Srinivasa R., Campbell J.A., Deinzer M.L. The photochemistry of polyhaloarenes. 5. Fragmentation pathways in polychlorobenzene radical anions. J. Am. Chem. Soc. 1986, 108:5531-5536.
48. Fu Q.S., Barkovskii A.L., Adriaens P. Reductive transformation of dioxins: an assessment of the contribution of dissolved organic matter to dechlorination reactions. Environ. Sci. Technol. 1999, 33:3837-3842.
49. Fu J., Wang Y., Zhang A., Zhang Q., Zhao Z., Wang T., Jiang G. Spatial distribution of polychlorinated biphenyls (PCBs) and polybrominated biphenyl ethers (PBDEs) in an e-waste dismantling region in Southeast China: use of apple snail (Ampullariidae) as a bioindicator. Chemosphere 2011, 82:648-655.
50. Fu L.Y., Luo J., Hu J.W. A quantitative structure-property relationship study on photodegradation of polybrominated diphenyl ethers. Adv. Mater. Res. 2012, 546-547:48-53.
51. Fueno H., Tanaka K., Sugawa S. Theoretical study of the dechlorination reaction pathways of octachlorodibenzo-p-dioxin. Chemosphere 2002, 48:771-778.
52. Fukui K., Yonezawa T., Nagata C., Shingu H. Molecular orbital theory of orientation in aromatic, heteroaromatic, and other conjugated molecules. J. Chem. Phys. 1954, 22:1433-1442.
53. Gao H., Shreeve J.N.M. Azole-based energetic salts. Chem. Rev. 2011, 111:7377-7436.
54. Garson G.D. Interpreting neural-network connection weights. AI Expert 1991, 6:46-51.
55. Gillham R.W., O'Hannesin S.F. Enhanced degradation of halogenated aliphatics by zero-valent iron. Ground Water 1994, 32:958-967.
56. Goh A.T.C. Back-propagation neural networks for modeling complex systems. Artif. Intell. Eng. 1995, 9:143-151.
57. Golon L., Chomicz L., Rak J. Electron-induced single strand break in the nucleotide of 5-and 6-bromouridine. A DFT study. Chem. Phys. Lett. 2014, 612:289-294.
58. Grabda M., Oleszek-Kudlak S., Shibata E., Nakamura T. Gas phase thermodynamic properties of PBDEs, PBBs, PBPs, HBCD and TBBPA predicted using DFT method. J. Mol. Struct.: Theochem 2007, 822:38-44.
59. Gribble G.W. The diversity of naturally produced organohalogens. Chemosphere 2003, 52:289-297.
60. Gu C.G., Ju X.H., Jiang X., Wang F., Yang S.G., Sun C. DFT study on the bromination pattern dependence of electronic properties and their validity in quantitative structure-activity relationships of polybrominated diphenyl ethers. SAR QSAR Environ. Res. 2009, 20:287-307.
61. Häggblom M.M., Bossert I.D. Halogenated organic compounds-a global perspective. Dehalogenation 2004, 3-29. Springer, US. M.M. Häggblom, I.D. Bossert (Eds.).
62. Haglund P.S., Zook D.R., Buser H.R., Hu J. Identification and quantification of polybrominated diphenyl ethers and methoxy-polybrominated diphenyl ethers in Baltic biota. Environ. Sci. Technol. 1997, 31:3281-3287.
63. Harper D. Halomethane from halide ion-a highly efficient fungal conversion of environmental significance. Nature 1985, 315:55-57.
64. Heimstad E.S., Bastos P.M., Eriksson J., Bergman Å., Harju M. Quantitative structure-photodegradation relationships of polybrominated diphenyl ethers, phenoxyphenols and selected organochlorines. Chemosphere 2009, 77:914-921.
65. Hertz-Picciotto I., Park H.Y., Dostal M., Kocan A., Trnovec T., Sram R. Prenatal exposures to persistent and non-persistent organic compounds and effects on immune system development. Basic. Clin. Pharmacol. 2008, 102:146-154.
66. Hites R.A. Polybrominated diphenyl ethers in the environment and in people: a meta-analysis of concentrations. Environ. Sci. Technol. 2004, 38:945-956.
67. Holmes D.A., Harrison B.K., Dolfing J. Estimation of Gibbs free energies of formation for polychlorinated biphenyls. Environ. Sci. Technol. 1993, 27:725-731.
68. Horowitz A., Suflita J.M., Tiedje J.M. Reductive dehalogenations of halobenzoates by anaerobic lake sediment microorganisms. Appl. Environ. Microb. 1983, 45:1459-1465.
69. 13C NMR spectroscopy and conformational properties of 18 halogenated diphenyl ethers. Chemosphere 1994, 28:1069-1078.
70. Hu J., Eriksson L., Bergman A., Kolehmainen E., Knuutinen J., Suontamo R., Wei X. Molecular orbital studies on brominated diphenyl ethers. Chemosphere 2005, 59:1033-1041.
71. Hu J., Eriksson L., Bergman A., Jakobsson E., Kolehmainen E., Knuutinen J., Suontamo R., Wei X. Molecular orbital studies on brominated diphenyl ethers. Part II-reactivity and quantitative structure-activity (property) relationships. Chemosphere 2005, 59:1043-1057.
72. Hu J., Zhang X., Wang Z. A review on progress in QSPR studies for surfactants. Int. J. Mol. Sci. 2010, 11:1020-1047.
73. Hu J.W., Zhuang Y., Luo J., Wei X.H., Huang X.F. A theoretical study on reductive debromination of polybrominated diphenyl ethers. Int. J. Mol. Sci. 2012, 13:9332-9342.
74. Hu J.W., Zhuang Y., Luo J., Wei X.H. A quantitative structure-property relationship study on reaction rate constants for reductive debromination of polybrominated diphenyl ethers by zero-valent iron. Adv. Mater. Res. 2012, 550-553:2668-2675.
75. Hua I., Kang N., Jafvert C.T., Fábrega-Duque J.R. Heterogeneous photochemical reactions of decabromodiphenyl ether. Environ. Toxic. Chem. 2003, 22:798-804.
76. Huang C.L., Harrison B.K., Madura J., Dolfing J. Gibbs free energies of formation of PCDDs: evaluation of estimation methods and application for predicting dehalogenation pathways. Environ. Toxicol. Chem. 1996, 15:824-836.
77. Ikonomou M.G., Rayne S., Fischer M., Fernandez M.P., Cretney W. Occurrence and congener profiles of polybrominated diphenyl ethers (PBDEs) in environmental samples from coastal British Columbia, Canada. Chemosphere 2002, 46:649-663.
78. Ji K., Choi K., Giesy J.P., Musarrat J., Takeda S. Genotoxicity of several polybrominated diphenyl ethers (PBDEs) and hydroxylated PBDEs, and their mechanisms of toxicity. Environ. Sci. Technol. 2011, 45:5003-5008.
79. Jiang G.X., Niu J.F., Zhang S.P., Zhang Z.Y., Xie B. Prediction of biodegradation rate constants of hydroxylated polychlorinated biphenyls by fungal laccases from Trametes versicolor and Pleurotus ostreatus. Bull. Environ. Contam. Toxic. 2008, 81:1-6.
80. Johnson T.L., Scherer M.M., Tratnyek P.G. Kinetics of halogenated organic compound degradation by iron metal. Environ. Sci. Technol. 1996, 30:2634-2640.
81. Jones K.C., De Voogt P. Persistent organic pollutants (POPs): state of the science. Environ. Pollut. 1999, 100:209-221.
82. Jones C.G., Silverman J., Al-Sheikhly M., Neta P., Poster D.L. Dechlorination of polychlorinated biphenyls in industrial transformer oil by radiolytic and photolytic methods. Environ. Sci. Technol. 2003, 37:5773-5777.
83. Jung B.M., Batchelor B., Park J.Y., Abdel-Wahab A. Linear free energy relationship analysis of chlorinated hydrocarbons in cement slurries. I.J. Environ. Res. 2014, 8:819-830.
84. Karelson M., Lobanov V.S., Katritzky A.R. Quantum-chemical descriptors in QSAR/QSPR studies. Chem. Rev. 1996, 96:1027-1044.
85. Kebarle P., Chowdhury S. Electron affinities and electron-transfer reactions. Chem. Rev. 1987, 87:513-534.
86. Keum Y.S., Li Q.X. Reductive debromination of polybrominated diphenyl ethers by zero-valent iron. Environ. Sci. Technol. 2005, 39:2280-2286.
87. Kim Y.H., Carraway E.R. Dechlorination of chlorinated phenols by zero-valent zinc. Environ. Technol. 2003, 24:1455-1463.
88. Kim J.H., Tratnyek P.G., Chang Y.S. Rapid dechlorination of polychlorinated dibenzo-p-dioxins by bimetallic and nanosized zero-valent iron. Environ. Sci. Technol. 2008, 42:4106-4112.
89. Kim J.H., Tratnyek P.G., Kim J.H., Chang Y.S. Modeling the reductive dechlorination of polychlorinated dibenzo-p-dioxins: kinetics, pathway, and equivalent toxicity. Environ. Sci. Technol. 2009, 43:5327-5332.
90. Kim E.J., Kim J.H., Kim J.H., Bokare V., Chang Y.S. Predicting reductive debromination of polybrominated diphenyl ethers by nanoscale zerovalent iron and its implications for environmental risk assessment. Sci. Total Environ. 2013, 470:1553-1557.
91. Kissa E. Fluorinated surfactants and repellants 2001, Marcel Dekker Inc., NY.
92. Lee J.E., Choi W., Mhin B.J. DFT calculation on the thermodynamic properties of polychlorinated dibenzo-p-dioxins: intramolecular Cl-Cl repulsion effects and their thermochemical implications. J. Phys. Chem. A 2003, 107:2693-2699.
93. Lee J.E., Choi W., Mhin B.J. DFT calculation on the electron affinity of polychlorinated dibenzo-p-dioxins. Bull. Korean Chem. Soc. 2003, 24:792-796.
94. Legler J., Brouwer A. Are brominated flame retardants endocrine disruptors?. Environ. Int. 2003, 29:879-885.
95. Lewis A., Bumpus J.A., Truhlar D.G., Cramer C.J. Molecular modeling of environmentally important processes: reduction potentials. J. Chem. Edu. 2004, 81:596-604.
96. Li X.W., Shibata E., Nakamura T. Thermodynamic properties of polybrominated dibenzo-p-dioxins and dibenzofurans calculated by density functional theory. Mater. Trans. 2003, 44:1004-1013.
97. Li X.Q., Elliott D.W., Zhang W.X. Zero-valent iron nanoparticles for abatement of environmental pollutants: materials and engineering aspects. Crit. Rev. Solid State Mater. Sci. 2006, 31:111-122.
98. Li A., Tai C., Zhao Z., Wang Y., Zhang Q., Jiang G., Hu J. Debromination of decabrominated diphenyl ether by resin-bound iron nanoparticles. Environ. Sci. Technol. 2007, 41:6841-6846.
99. Li X., Fang L., Huang J., Yu G. Photolysis of mono-through deca-chlorinated biphenyls by ultraviolet irradiation in n-hexane and quantitative structure-property relationship analysis. J. Environ. Sci. 2008, 20:753-759.
100. Li Y., Zhou Q., Wang Y., Xie X. Fate of tetrabromobisphenol A and hexabromocyclododecane brominated flame retardants in soil and uptake by plants. Chemosphere 2011, 82:204-209.
101. Li L.Y., Lin Y.M., Hu J.W. A study on pathway and QSPR models for debromination of PBDEs with pseudopotential method. Adv. Mater. Res. 2014, 997:25-32.
102. Li L.Y., Lin Y.M., Hu J.W. A QSPR study on debromination of PBDEs with CPCM solvation model. Adv. Mater. Res. 2014, 1010-1012:3-9.
103. Li X., Fang J., Liu G., Zhang S., Pan B., Ma J. Kinetics and efficiency of the hydrated electron-induced dehalogenation by the sulfite/UV process. Water Res. 2014, 62:220-228.
104. Lim D.H., Lastoskie C.M. Density functional theory studies on the relative reactivity of chloroethenes on zero-valent iron. Environ. Sci. Technol. 2009, 43:5443-5448.
105. Lim D.H., Lastoskie C.M., Soon A., Becker U. Density functional theory studies of chloroethene adsorption on zero-valent iron. Environ. Sci. Technol. 2009, 43:1192-1198.
106. Liu Z., Wang L., Zhou F. Quantitative structure-free energy relationship for the dehalogenation of halogenated aromatic compounds. Chemosphere 1994, 29:1683-1689.
107. Lovelock J.E. Natural halocarbons in the air and in the sea. Nature 1975, 256:193-194.
108. Lu G.N., Dang Z., Fennell D.E., Huang W., Li Z., Liu C.Q. Rules of thumb for assessing reductive dechlorination pathways of PCDDs in specific systems. J. Hazard. Mater. 2010, 177:1145-1149.
109. Luke B.T., Loew G.H., McLean A.D. Theoretical investigation of the anaerobic reduction of halogenated alkanes by cytochrome P-450. 2. Vertical electron affinities of chlorofluoromethanes as a measure of their activity. J. Am. Chem. Soc. 1988, 110:3396-3400.
110. Luo Q., Wong M., Cai Z. Determination of polybrominated diphenyl ethers in freshwater fishes from a river polluted by e-wastes. Talanta 2007, 72:1644-1649.
111. Luo J., Hu J., Zhuang Y., Wei X., Huang X. Theoretical study on the radical anions and reductive dechlorination of selected polychlorinated dibenzo-p-dioxins. Chemosphere 2013, 91:765-770.
112. Luo J., Hu J., Zhuang Y., Wei X., Huang X. Electron-induced reductive debromination of 2,3,4-tribromodiphenyl ether: a computational study. J. Mol. Model. 2013, 19:3333-3338.
113. Lynam M.M., Kuty M., Damborsky J., Koca J., Adriaens P. Molecular orbital calculations to describe microbial reductive dechlorination of polychlorinated dioxins. Environ. Toxicol. Chem. 1998, 17:988-997.
114. McDaniel D.H., Brown H.C. A quantitative approach to the ortho effects of halogen substituents in aromatic systems. J. Am. Chem. Soc. 1955, 77:3756-3763.
115. McFarland V.A., Clarke J.U. Environmental occurrence, abundance, and potential toxicity of polychlorinated biphenyl congeners: considerations for a congener-specific analysis. Environ. Health Persp. 1989, 81:225-239.
116. Meijer S.N., Ockenden W.A., Sweetman A., Breivik K., Grimalt J.O., Jones K.C. Global distribution and budget of PCBs and HCB in background surface soils: implications for sources and environmental processes. Environ. Sci. Technol. 2003, 37:667-672.
117. Mennucci B., Tomasi J., Cammi R., Cheeseman J.R., Frisch M.J., Devlin F.J., Gabriel S., Stephens P.J. Polarizable continuum model (PCM) calculations of solvent effects on optical rotations of chiral molecules. J. Phys. Chem. A 2002, 106:6102-6113.
118. Miehr R., Tratnyek P.G., Bandstra J.Z., Scherer M.M., Alowitz M.J., Bylaska E.J. Diversity of contaminant reduction reactions by zerovalent iron: role of the reductate. Environ. Sci. Technol. 2004, 38:139-147.
119. Mohn W.W., Tiedje J.M. Microbial reductive dehalogenation. Microb. Rev. 1992, 56:482-507.
120. Moore M.R., Vetter W., Gaus C., Shaw G.R., Müller J.F. Trace organic compounds in the marine environment. Mar. Pollut. Bull. 2002, 45:62-68.
121. Mueller N.C., Braun J., Bruns J., Černík M., Rissing P., Rickerby D., Nowack B. Application of nanoscale zero valent iron (NZVI) for groundwater remediation in Europe. Environ. Sci. Pollut. Res. 2012, 19:550-558.
122. Muir D.C., Howard P.H. Are there other persistent organic pollutants? A challenge for environmental chemists. Environ. Sci. Technol. 2006, 40:7157-7166.
123. Mulholland J.A., Sarofim A.F., Rutledge G.C. Semiempirical molecular orbital estimation of the relative stability of polychlorinated biphenyl isomers produced by o-dichlorobenzene pyrolysis. J. Phys. Chem. 1993, 97:6890-6896.
124. Müller N.C., Nowack B. Nano zero-valent iron - the solution for water and soil remediation. Report of the ObservatoryNANO 2010, 1-34.
125. Nevalainen T., Rissanen K. AM1 and single-crystal X-ray diffraction study of the conformational properties of chlorinated diphenyl ethers. J. Chem. Soc. Perkin Trans. 1994, 271-279.
126. Niu J., Shen Z., Yang Z., Long X., Yu G. Quantitative structure-property relationships on photodegradation of polybrominated diphenyl ethers. Chemosphere 2006, 64:658-665.
127. Nonnenberg C., Van der Donk W.A., Zipse H. Reductive dechlorination of trichloroethylene: a computational study. J. Phys. Chem. A 2002, 106:8708-8715.
128. Noubactep C., Caré S., Crane R. Nanoscale metallic iron for environmental remediation: prospects and limitations. Water Air Soil Pollut. 2012, 223(3):1363-1382.
129. Ohura T., Amagai T., Makino M. Behavior and prediction of photochemical degradation of chlorinated polycyclic aromatic hydrocarbons in cyclohexane. Chemosphere 2008, 70:2110-2117.
130. Olden J.D., Jackson D.A. Illuminating the "black box": a randomization approach for understanding variable contributions in artificial neural networks. Ecol. Model. 2002, 154:135-150.
131. Onanong S., Comfort S.D., Burrow P.D., Shea P.J. Using gas-phase molecular descriptors to predict dechlorination rates of chloroalkanes by zerovalent iron. Environ. Sci. Technol. 2007, 41:1200-1205.
132. Orozco M., Luque F.J. Theoretical methods for the description of the solvent effect in biomolecular systems. Chem. Rev. 2000, 100:4187.
133. Paasivirta J. Foreword. New types of persistent halogenated compounds 2000, vol. 3:XIII. Springer, Berlin.
134. Pan L., Bian W. Theoretical study on the photodegradation mechanism of Nona-BDEs in methanol. ChemPhysChem 2013, 14:1264-1271.
135. Pan L., Bian W., Zhang J. The effect of explicit solvent on photodegradation of decabromodiphenyl ether in toluene: insights from theoretical study. J. Phys. Chem. A 2013, 117:5291-5298.
136. Parsons J.R., Sáez M., Dolfing J., De Voogt P. Biodegradation of perfluorinated compounds. Reviews of Environmental Contamination and Toxicology 2008, vol. 196:53-71. Springer, US.
137. Politzer P., Timberlake J.W. Anomalous properties of halogen substituents. J. Org. Chem. 1972, 37:3557-3559.
138. Pratt D.A., van der Donk W.A. Theoretical investigations into the intermediacy of chlorinated vinylcobalamins in the reductive dehalogenation of chlorinated ethylenes. J. Am. Chem. Soc. 2005, 127:384-396.
139. Puri S., Chickos J.S., Welsh W.J. Three-dimensional quantitative structure-property relationship (3D-QSPR) models for prediction of thermodynamic properties of polychlorinated biphenyls (PCBs): enthalpy of sublimation. J. Chem. Inf. Comput. Sci. 2002, 42:109-116.
140. Puri S., Chickos J.S., Welsh W.J. Three-dimensional quantitative structure-property relationship (3D-QSPR) models for prediction of thermodynamic properties of polychlorinated biphenyls (PCBs): enthalpies of fusion and their application to estimates of enthalpies of sublimation and aqueous solubilities. J. Chem. Inf. Comput. Sci. 2003, 43:55-62.
141. Puzyn T., Suzuki N., Haranczyk M., Rak J. Calculation of quantum-mechanical descriptors for QSPR at the DFT level: is it necessary?. J. Chem. Inf. Model. 2008, 48:1174-1180.
142. Qiu S., Tan X., Wu K., Zhang A., Han S., Wang L. Experimental and theoretical study on molecular structure and FT-IR, Raman, NMR spectra of 4,4'-dibromodiphenyl ether. Spectrochim. Acta A 2010, 76:429-434.
143. Ren Z., Zheng M. Impacts of human activities on dioxins emissions at national scale. Chemosphere 2009, 76:853-859.
144. Rienstra-Kiracofe J.C., Tschumper G.S., Schaefer H.F., Nandi S., Ellison G.B. Atomic and molecular electron affinities: photoelectron experiments and theoretical computations. Chem. Rev. 2002, 102:231-282.
145. Sadowsky D., McNeill K., Cramer C.J. Thermochemical factors affecting the dehalogenation of aromatics. Environ. Sci. Technol. 2013, 47:14194-14203.
146. Savéant J.M. A simple model for the kinetics of dissociative electron transfer in polar solvents. Application to the homogeneous and heterogeneous reduction of alkyl halides. J. Am. Chem. Soc. 1987, 109:6788-6795.
147. Savéant J.M. Dissociative electron transfer. New tests of the theory in the electrochemical and homogeneous reduction of alkyl halides. J. Am. Chem. Soc. 1992, 114:10595-10602.
148. Scherer M.M., Balko B.A., Gallagher D.A., Tratnyek P.G. Correlation analysis of rate constants for dechlorination by zero-valent iron. Environ. Sci. Technol. 1998, 32:3026-3033.
149. Schwerdtfeger P., Dolg M., Schwarz W.H.E., Bowmaker G.A., Boyd P.D.W. Relativistic effects in gold chemistry. I. Diatomic gold compounds. J. Chem. Phys. 1989, 91:1762-1774.
150. Shih Y.H., Tai Y.T. Reaction of decabrominated diphenyl ether by zero-valent iron nanoparticles. Chemosphere 2010, 78:1200-1206.
151. Shih Y.H., Wang C.K. Photolytic degradation of polybromodiphenyl ethers under UV-lamp and solar irradiations. J. Hazard. Mater. 2009, 165:34-38.
152. Song H., Carraway E.R. Reduction of chlorinated ethanes by nanosized zero-valent iron: kinetics, pathways, and effects of reaction conditions. Environ. Sci. Technol. 2005, 39:6237-6245.
153. Stricklett K.L., Chu S.C., Burrow P.D. Dissociative attachment in vinyl and allyl chloride, chlorobenzene and benzyl chloride. Chem. Phys. Lett. 1986, 131:279-284.
154. Su Y., Hung H., Sverko E., Fellin P., Li H. Multi-year measurements of polybrominated diphenyl ethers (PBDEs) in the Arctic atmosphere. Atmos. Environ. 2007, 41:8725-8735.
155. Suflita J.M., Robinson J.A., Tiedje J.M. Kinetics of microbial dehalogenation of haloaromatic substrates in methanogenic environments. Appl. Environ. Microb. 1983, 45:1466-1473.
156. Sun C., Chang W., Ma W., Chen C., Zhao J. Photoreductive debromination of decabromodiphenyl ethers in the presence of carboxylates under visible light irradiation. Environ. Sci. Technol. 2013, 47:2370-2377.
157. Teuten E.L., Reddy C.M. Halogenated organic compounds in archived whale oil: a pre-industrial record. Environ. Pollut. 2007, 145:668-671.
158. Teuten E.L., Xu L., Reddy C.M. Two abundant bioaccumulated halogenated compounds are natural products. Science 2005, 307:917-920.
159. Totten L.A., Roberts A.L. Calculated one-and two-electron reduction potentials and related molecular descriptors for reduction of alkyl and vinyl halides in water. Crit. Rev. Environ. Sci. Technol. 2001, 31:175-221.
160. Verma J., Khedkar V.M., Coutinho E.C. 3D-QSAR in drug design - a review. Curr. Top. Med. Chem. 2010, 10:95-115.
161. Vogel T.M., Criddle C.S., McCarty P.L. ES&T critical reviews: transformations of halogenated aliphatic compounds. Environ. Sci. Technol. 1987, 21:722-736.
162. Wang C.B., Zhang W.X. Synthesizing nanoscale iron particles for rapid and complete dechlorination of TCE and PCBs. Environ. Sci. Technol. 1997, 31:2154-2156.
163. Wang D., Cai Z., Jiang G., Leung A., Wong M.H., Wong W.K. Determination of polybrominated diphenyl ethers in soil and sediment from an electronic waste recycling facility. Chemosphere 2005, 60:810-816.
164. Wang Z.Y., Zhai Z.C., Wang L.S. Prediction of gas phase thermodynamic properties of polychlorinated dibenzo-furans by DFT. J. Mol. Struct.: THEOCHEM 2005, 725:55-62.
165. Wang Z.Y., Zhai Z.C., Wang L.S. Prediction of gas phase thermodynamic properties of polychlorinated dibenzo-furans by DFT. J. Mol. Struct.: Theochem 2005, 725:55-62.
166. Wang Z., Huang W., Fennell D.E., Peng P.A. Kinetics of reductive dechlorination of 1,2,3,4-TCDD in the presence of zero-valent zinc. Chemosphere 2008, 71:360-368.
167. Wang C., Fang Z.Y., Liu H., Xu S. Thermodynamic properties and relative stability of polybrominated phenoxathiins by density functional theory. Int. J. Phys. Sci. 2008, 3:250-256.
168. Wang S., Hao C., Gao Z., Chen J., Qiu J. Effects of excited-state structures and properties on photochemical degradation of polybrominated diphenyl ethers: A TDDFT study. Chemosphere 2012, 88:33-38.
169. Wang S., Hao C., Gao Z., Chen J., Qiu J. Theoretical investigation on photodechlorination mechanism of polychlorinated biphenyls. Chemosphere 2014, 95:200-205.
170. Wang S., Hao C., Gao Z., Chen J., Qiu J. Theoretical investigations on direct photolysis mechanisms of polychlorinated diphenyl ethers. Chemosphere 2014, 111:7-12.
171. Wania F., Mackay D. Global fractionation and cold condensation of low volatility organochlorine compounds in polar regions. Ambio 1993, 22:10-18.
172. Wei H., Zou Y., Li A., Christensen E.R., Rockne K.J. Photolytic debromination pathway of polybrominated diphenyl ethers in hexane by sunlight. Environ. Pollut. 2013, 174:194-200.
173. Woods S.L., Trobaugh D.J., Carter K.J. Polychlorinated biphenyl reductive dechlorination by vitamin B12s: thermodynamics and regiospecificity. Environ. Sci. Technol. 1999, 33:857-863.
174. Wu W.J., Qin N., Zhu Y., He Q.S., Ouyang H.L., He W., Liu W., Xu F.L. The residual levels and health risks of hexachlorocyclohexanes (HCHs) and dichloro-diphenyl-trichloroethanes (DDTs) in the fish from Lake Baiyangdian. Environ. Sci. Pollut. Res. 2013, 1-13.
175. Xie Q., Chen J., Shao J., Chen C.E., Zhao H., Hao C. Important role of reaction field in photodegradation of deca-bromodiphenyl ether: theoretical and experimental investigations of solvent effects. Chemosphere 2009, 76:1486-1490.
176. Xu W., Gao A. DFT study on the electron affinities of the chlorinated benzenes. J. Mol. Struct.: Theochem 2005, 732:63-70.
177. Yamada S., Kishita S., Nakai S., Takada M., Hosomi M. Photodechlorination of octachlorodibenzothiophene and octachlorodibenzofuran: comparison of experimental degradation pathways with degradation pathways predicted by DFT. Chemosphere 2008, 73:1005-1010.
178. ow) of polychlorinated dibenzo-p-dioxins (PCDDs). QSAR Comb. Sci. 2007, 26:352-357.
179. Yang X., Liu H., Hou H., Flamm A., Zhang X., Wang Z. Studies of thermodynamic properties and relative stability of a series of polyfluorinated dibenzo-p-dioxins by density functional theory. J. Hazard. Mater. 2010, 181:969-974.
180. Yuan L.X., Yu J., Wang Z.Y., Liu H.X., Ju X.H. Thermodynamic property and relative stability of 76 polybrominated naphthalenes by density functional theory. J. Chem. Eng. Data 2006, 51:2032-2037.
181. a values for fluorinated isomers of toluene. Comput. Theor. Chem. 2013, 1011:21-29.
182. Zeng X., Freeman P.K., Vasil'ev Y.V., Voinov V.G., Simonich S.L., Barofsky D.F. Theoretical calculation of thermodynamic properties of polybrominated diphenyl ethers. J. Chem. Eng. Data 2005, 50:1548-1556.
183. Zeng X., Simonich S.L.M., Robrock K.R., Korytár P., Alvarez-Cohen L., Barofsky D.F. Development and validation of a congener-specific photodegradation model for polybrominated diphenyl ethers. Environ. Toxicol. Chem. 2008, 2(7):2427-2435.
184. 0 reduction of polybrominated diphenyl ethers. Environ. Toxicol. Chem. 2010, 29:770-778.
185. Zeng X.L., Zhang X.L., Wang Y. QSPR modeling of n-octanol/air partition coefficients and liquid vapor pressures of polychlorinated dibenzo-p-dioxins. Chemosphere 2013, 91:229-232.
186. Zhai Z.C., Wang Z.Y., Chen X.H., Wang L.S. DFT calculation on 204 polychlorinated biphenyls: their thermodynamic function and implication of Cl substitute position. J. Mol. Struct.: Theochem 2005, 714:123-131.
187. Zhao H., Chen J., Quan X., Yang F., Peijnenburg W.J.G.M. Quantitative structure-property relationship study on reductive dehalogenation of selected halogenated aliphatic hydrocarbons in sediment slurries. Chemosphere 2001, 44:1557-1563.
188. Zhao Y.Y., Tao F.M., Zeng E.Y. Structures, reductive dechlorination, and electron affinities of selected polychlorinated dibenzo-p-dioxins: Density functional theory study. J. Phys. Chem. A 2007, 111:11638-11644.
189. Zhao Y.Y., Tao F.M., Zeng E.Y. Theoretical study on the chemical properties of polybrominated diphenyl ethers. Chemosphere 2008, 70:901-907.
190. Zhou J., Chen J., Liang C.H., Xie Q., Wang Y.N., Zhang S., Qiao X., Li X. Quantum chemical investigation on the mechanism and kinetics of PBDE photooxidation by OH: a case study for BDE-15. Environ. Sci. Technol. 2011, 45:4839-4845.
191. Zhu L., Bozzelli J.W., Lay T.H. Comparison of AM1 and PM3 in MOPAC6 with literature for the thermodynamic parameters of C1 and C2 chlorocarbons. Ind. Eng. Chem. Res. 1998, 37:3497-3507.
192. Zhuang Y., Ahn S., Luthy R.G. Debromination of polybrominated diphenyl ethers by nanoscale zero-valent iron: pathways, kinetics, and reactivity. Environ. Sci. Technol. 2010, 44:8236-8242.
193. Zhuang Y., Ahn S., Seyfferth A.L., Masue-Slowey Y., Fendorf S., Luthy R.G. Dehalogenation of polybrominated diphenyl ethers and polychlorinated biphenyl by bimetallic, impregnated, and nanoscale zero-valent iron. Environ. Sci. Technol. 2011, 45:4896-4903.
194. Zhuang Y., Jin L., Luthy R.G. Kinetics and pathways for the debromination of polybrominated diphenyl ethers by bimetallic and nanoscale zerovalent iron: effects of particle properties and catalyst. Chemosphere 2012, 89:426-432.
195. Zou Y., Christensen E.R., Zheng W., Wei H., Li A. Estimating stepwise debromination pathways of polybrominated diphenyl ethers with an analogue Markov Chain Monte Carlo algorithm. Chemosphere 2014, 114:187-194.