Abstract
Batch photodegradation of pentachlorophenol (PCP) was conducted with ultraviolet irradiation. The main intermediates were identified as 2,3,5,6-tetrachlorophenol, 2,3,4,6-tetrachlorophenol and 2,5-dichlorophenol. Based on the density functional theory, atomic charge values were applied to reveal the photodegradation pathway. A comparison of the results of the experiment confirms that PCP molecules are dechlorinated in the descending order of their atomic charge values. From these results, it appears that determining the atomic charge values of organohalogen compounds is a promising method for predicting the dechlorination position in photodegradation.
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References
Akai N, Kudoh S, Takayanagi M, Nakata M (2001) Photoreaction mechanisms of 2-chlorophenol and its multiple chloro-substituted derivatives studied by low-temperature matrix-isolation infrared spectroscopy and density-functional-theory calculations. J Photochem Photobiol Chem 146:49–57. doi:10.1016/S1010-6030(01)00555-X
Foresman J, Frisch A (1996) Exploring chemistry with electronic structure methods. Gaussian Inc., Pittsburgh
Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Zakrzewski VG, Montgomery JA, Stratmann RE, Burant JC, Dapprich S, Millam JM, Daniels AD, Kudin KN, Strain MC, Farkas O, Tomasi J, Barone V, Cossi M, Cammi R, Mennucci B, Pomelli C, Adamo C, Clifford S, Ochterski J, Petersson GA, Ayala PY, Cui Q, Morokuma K, Rega N, Salvador P, Dannenberg JJ, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Cioslowski J, Ortiz JV, Baboul AG, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Gomperts R, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PM, Johnson B, Chen W, Wong MW, Andres JL, Gonzalez C, Head-Gordon M, Replogle ES, Pople JA (2001) Gaussian 98. Gaussian Inc., Pittsburgh
Fueno H, Tanaka K, Sugawa S (2002) Theoretical study of the dechlorination reaction pathways of octachlorodibenzo-p-dioxin. Chemosphere 48:771–778. doi:10.1016/S0045-6535(02)00141-8
Hong J, Kim D, Cheong C, Jung S, Yoo M, Kim K, Kim T, Park Y (2000) Identification of photolytical transformation products of pentachlorophenol in water. Anal Sci 16:621–626. doi:10.2116/analsci.16.621
Lee C, Yang W, Parr R (1988) Development of the Colle-Salvetti correlation energy formula into a functional of the electron density. Phys Rev B 37:785–789. doi:10.1103/PhysRevB.37.785
Mineva T, Russo N (1997) Solvent effects computed with the Gaussian density functional method. Int J Quantum Chem 61:665–671. doi:10.1002/(SICI)1097-461X(1997)61:4<665::AID-QUA8>3.0.CO;2-U
Suegra J, Lee B-D, Espino MP, Nakai S, Hosomi M (2005) Photodegradation of pentachlorophenol and its degradation pathways predicted using density functional theory. Chemosphere 61:341–346. doi:10.1016/j.chemosphere.2005.02.090
Acknowledgments
This research is funded by the Gyeongbuk Environmental Technology Development Center under the Research Development Program (Yr 2006) of Korean Government and the authors would like to acknowledge for the assistance.
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Lee, BD., Hosomi, M. Presumed decomposition pathway of pentachlorophenol through atomic charge calculation and photodecomposition experiments. Environ Chem Lett 8, 139–143 (2010). https://doi.org/10.1007/s10311-009-0200-7
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DOI: https://doi.org/10.1007/s10311-009-0200-7