Photodegradation of hexachlorobenzene and theoretical prediction of its degradation pathways using quantum chemical calculation.

Experimentally determined photodegradation pathways of hexachlorobenzene (HCB), a chlorinated aromatic compound, in hexane, 2-propanol (IPA), and methanol were compared with those predicted by quantum chemical calculation based on density functional theory (DFT), and the adequacy of the prediction method was evaluated. The experimental main degradation pathways of HCB were virtually the same for the three solvents and also agreed with the predicted main degradation pathways. In the DFT method, the main degradation product was the dechlorinated benzene at the position where the C-Cl bond was predicted to have the lowest bond dissociation energy. This result suggested that the photodechlorination pathways of chlorinated aromatic compounds could be predicted by comparing the bond dissociation energies calculated with the DFT method.