Theoretical investigation on photodechlorination mechanism of polychlorinated biphenyls

Chemosphere

Volumn 95, Issue , 2014, Pages 200-205

  Wang, Se ^a   Hao, Ce ^a   Gao, Zhanxian ^a   Chen, Jingwen ^a   Qiu, Jieshan ^a  

^a DALIAN UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

Pathway; Photodechlorination; Photoproduct; Polychlorinated biphenyls; TDDFT

Indexed keywords

ACTIVATION ENERGY; BENZENE; CHEMICAL BONDS; CHLORINE COMPOUNDS; DISSOCIATION; EXCITED STATES; GROUND STATE; PHOTOREACTIVITY; POLYCHLORINATED BIPHENYLS; QUANTUM CHEMISTRY;

BOND DISSOCIATION ENERGIES; PATHWAY; PHOTODECHLORINATION; PHOTOPRODUCTS; POLYCHLORINATED BIPHENYL (PCBS); QUANTUM CHEMISTRY CALCULATIONS; TDDFT; THEORETICAL INVESTIGATIONS;

ORGANIC POLLUTANTS;

BENZENE; CARBON; CHLORINE; HYDROGEN; POLYCHLORINATED BIPHENYL; POLLUTANT;

CHEMICAL BONDING; DECHLORINATION; ENVIRONMENTAL FATE; EXPERIMENTAL STUDY; PCB; PHOTODEGRADATION; THEORETICAL STUDY;

ARTICLE; CHEMICAL BOND; DECHLORINATION; DENSITY FUNCTIONAL THEORY; PHOTODECHLORINATION; PHOTOREACTIVITY; QUANTUM CHEMISTRY; CHEMICAL MODEL; CHEMISTRY; HALOGENATION; PHOTOCHEMISTRY; POLLUTANT;

ENVIRONMENTAL POLLUTANTS; HALOGENATION; MODELS, CHEMICAL; PHOTOCHEMICAL PROCESSES; POLYCHLORINATED BIPHENYLS;

EID: 84887610432     PISSN: 00456535     EISSN: 18791298     Source Type: Journal    
DOI: 10.1016/j.chemosphere.2013.08.066     Document Type: Article

References (46)

1. Almenningen A., Bastiansen O., Fernholt L. Structure and barrier of internal rotation of biphenyl derivatives in the gaseous state: Part 1. The molecular structure and normal coordinate analysis of normal biphenyl and pedeuterated biphenyl. J. Mol. Struct. 1985, 128:59-76.
2. Becke A.D. Density-functional thermochemistry. III. The role of exact exchange. J. Chem. Phys. 1993, 98:5648-5652.
3. Chang F.-C., Chiu T.-C., Yen J.-H., Wang Y.-S. Dechlorination pathways of ortho-substituted PCBs by UV irradiation in n-hexane and their correlation to the charge distribution on carbon atom. Chemosphere 2003, 51:775-784.
4. Diamond M.L., Melymuk L., Csiszar S.A., Robson M. Estimation of PCBs stocks, emissions, and urban fate: will our policies reduce concentrations and exposure?. Environ. Sci. Technol. 2010, 44:2777-2783.
5. Eyheraguibel B., Ter Halle A., Richard C. Photodegradation of bentazon, clopyralid, and triclopyr on model leaves: importance of a systematic evaluation of pesticide photostability on crops. J. Agric. Food Chem. 2009, 57:1960-1966.
6. Fang L., Huang J., Yu G., Wang L. Photochemical degradation of six polybrominated diphenyl ether congeners under ultraviolet irradiation in hexane. Chemosphere 2008, 71:258-267.
7. 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. Ecotoxicol. Environ. Saf. 2009, 72:1587-1593.
8. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Scalmani G., Barone V., Mennucci B., Petersson G.A., Nakatsuji H., Caricato M., Li X., Hratchian H.P., Izmaylov A.F., Bloino J., Zheng G., Sonnenberg J.L., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Vreven T., Montgomery J.A., Peralta J.E., Ogliaro F., Bearpark M., Heyd J.J., Brothers E., Kudin K.N., Staroverov V.N., Kobayashi R., Normand J., Raghavachari K., Rendell A., Burant J.C., Iyengar S.S., Tomasi J., Cossi M., Rega N., Millam J.M., Klene M., Knox J.E., 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., Martin R.L., Morokuma K., Zakrzewski V.G., Voth G.A., Salvador P., Dannenberg J.J., Dapprich S., Daniels A.D., Farkas O., Foresman J.B., Ortiz J.V., Cioslowski J., Fox D.J. Gaussian 09 Package 2009, Gaussian, Inc., Wallingford CT.
9. Gerofke A., Kömp P., McLachlan M.S. Bioconcentration of persistent organic pollutants in four species of marine phytoplankton. Environ. Toxicol. Chem. 2005, 24:2908-2917.
10. Halladja S., Amine-Khodja A., Ter Halle A., Boulkamh A., Richard C. Photolysis of fluometuron in the presence of natural water constituents. Chemosphere 2007, 69:1647-1654.
11. Hornbuckle K.C., Robertson L.W. Polychlorinated biphenyls (PCBs): sources, exposures, toxicities. Environ. Sci. Technol. 2010, 44:2749-2751.
12. Hutzinger O., Safe S., Zitko V. Photochemical degradation of chlorobiphenyls (PCBs). Environ. Health Perspect. 1972, 1:15-20.
13. Izadifard M., Achari G., Langford C.H. The pathway of dechlorination of PCB congener by a photochemical chain process in 2-propanol: the role of medium and quenching. Chemosphere 2008, 73:1328-1334.
14. Jahnke A., Mayer P., McLachlan M.S. Sensitive equilibrium sampling to study polychlorinated biphenyl disposition in Baltic sea sediment. Environ. Sci. Technol. 2012, 46:10114-10122.
15. Kovacevic G., Sabljic A. Theoretical study on the mechanism and kinetics of addition of hydroxyl radicals to fluorobenzene. J. Comput. Chem. 2013, 34:646-655.
16. Kovacevic G., Sabljic A. Mechanisms and reaction-path dynamics of hydroxyl radical reactions with aromatic hydrocarbons: the case of chlorobenzene. Chemosphere 2013, 92:851-856.
17. Langford C.H., Achari G., Izadifard M. Wavelength dependence of luminescence and quantum yield in dechlorination of PCBs. J. Photochem. Photobiol. A 2011, 222:40-46.
18. Lépine F.L., Milot S.M., Vincenet N.M., Gravel D. Photochemistry of higher chlorinated PCBs in cyclohexane. J. Agric. Food Chem. 1991, 39:2053-2058.
19. 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.-China 2008, 20:753-759.
20. * valence excited states. J. Phys. Chem. A 2005, 109:8209-8217.
21. Ljubić I., Sabljić A. Theoretical study of structure, vibrational frequencies, and electronic spectra of polychlorinated dibenzo-p-dioxins. J. Phys. Chem. A 2006, 110:4524-4534.
22. Ljubić I., Sabljić A. CASSCF/CASPT2 and TD-DFT study of valence and Rydberg electronic transitions in fluorene, carbazole, dibenzofuran, and dibenzothiophene. J. Phys. Chem. A 2011, 115:4840-4850.
23. Lores M., Llompart M., González-García R., González-Barreiro C., Cela R. On-fibre photodegradation studies of polychlorinated biphenyls using SPME-GC-MS-MS: a new approach. Chemosphere 2002, 47:607-615.
24. Matykiewiczová N., Klánová J., Klán P. Photochemical degradation of PCBs in snow. Environ. Sci. Technol. 2007, 41:8308-8314.
25. Miao X.-S., Chu S.-G., Xu X.-B. Photodegradation of 2,2',5,5'-tetrachlorobiphenyl in hexane. Bull. Environ. Contam. Toxicol. 1996, 56:571-574.
26. Miao X.-S., Chu S.-G., Xu X.-B. Degradation pathways of PCBs upon UV irradiation in hexane. Chemosphere 1999, 39:1639-1650.
27. Norström K., Czub G., McLachlan M.S., Hu D., Thorne P.S., Hornbuckle K.C. External exposure and bioaccumulation of PCBs in humans living in a contaminated urban environment. Environ. Int. 2010, 36:855-861.
28. Richard C., Krajnik P., Grabner G. Photolysis of 4-chlororesorcinol in water: competitive formation of a singlet ketene and a triplet carbine. Phys. Chem. Chem. Phys. 2010, 12:14322-14329.
29. Ruzo L.O., Zabik M.J., Schuetz R.D. Photochemistry of bioactive compounds. Photochemical processes of polychlorinated biphenyls. J. Am. Chem. Soc. 1974, 96:3809-3813.
30. Sabljic A. QSAR models for estimating properties of persistent organic pollutants required in evaluation of their environmental fate and risk. Chemosphere 2001, 43:363-375.
31. Safe S., Hutzinger O. Polychlorinated biphenyls: photolysis of 2,4,6,2',4',6'-hexachlorobiphenyl. Nature 1971, 232:641-642.
32. n (n=3-5) clusters. J. Lumin. 2011, 131:2279-2285.
33. 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.
34. 2O complex in electronic excited state. J. Mol. Model. 2013, 19:1913-1918.
35. Wania F., Mackay D. Tracking the distribution of persistent organic pollutants. Environ. Sci. Technol. 1996, 30:390A-396A.
36. Xiao W., Zhang J., Liang J., Zhu H., Zhou Z., Wu Q. Adverse effects of neonatal exposure to 3,3',4,4',5,5'-hexachlorobiphenyl on hormone levels and testicular function in male Spraque-Dawley rats. Environ. Toxicol. 2011, 26:657-668.
37. Yamada S., Naito Y., Takada M., Nakai S., Hosomi M. Photodegradation of hexachlorobenzene and theoretical prediction of its degradation pathways using quantum chemical calculation. Chemosphere 2008, 70:731-736.
38. Yanai T., Tew D.P., Handy N.C. A new hybrid exchange-correlation functional using the Coulomb-attenuating method (CAM-B3LYP). Chem. Phys. Lett. 2004, 393:51-57.
39. Yao Y., Kakimoto K., Ogawa H.I., Kato Y., Kadokami K., Shinohara R. Further study on the photochemistry of non-ortho substituted PCBs by UV irradiation in alkaline 2-propanol. Chemosphere 2000, 40:951-956.
40. Zacs D., Bartkevics V., Viksna A. Content of polychlorinated dibenzo-p-dioxins, dibenzofurans and dioxin-like polychlorinated biphenyls in fish from Latvian lakes. Chemosphere 2013, 91:179-186.
41. Zhao G.-J., Han K.-L. Novel infrared spectra for intermolecular dihydrogen bonding of the phenol-borane-trimethylamine complex in electronically excited state. J. Chem. Phys. 2007, 127:024306.
42. Zhao G.-J., Han K.-L. Early time hydrogen-bonding dynamics of photoexcited coumarin 102 in hydrogen-donating solvents: theoretical study. J. Phys. Chem. A 2007, 111:2469-2474.
43. Zhao G.-J., Han K.-L. Site-specific salvation of the photoexcited protochlrophyllide a in methanol: formation of the hydrogen-bonded intermediate state induced by hydrogen-bond strengthening. Biophys. J. 2008, 94:38-46.
44. Zhao G.-J., Han K.-L. PH-Controlled twisted intramolecular charge transfer (TICT) excited state via changing the charge transfer direction. Phys. Chem. Chem. Phys. 2010, 12:8914-8918.
45. Zhao G.-J., Han K.-L. Hydrogen bonding in the electronic excited state. Acc. Chem. Res. 2012, 45:404-413.
46. Zhao G.-J., Liu J.-Y., Zhou L.-C., Han K.-L. Site-selective photoinduced electron transfer from alcoholic solvents to the chromophore facilitated by hydrogen bonding: a new fluorescence quenching mechanism. J. Phys. Chem. B 2007, 111:8940-8945.