4.7 Article

Ultraviolet photolysis of monochloro-p-benzoquinone (MCBQ) in aqueous solution: Theoretical investigation into the dechlorination

期刊

CHEMOSPHERE
卷 291, 期 -, 页码 -

出版社

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.chemosphere.2021.132884

关键词

Monochloro-p-benzoquinone; UV irradiation; Dechlorination; Quantum chemical calculations

资金

  1. National Natural Science Foundation of China [52100188, 51908143]
  2. Natural Science Foundation of Jiangsu Province, China [BK20200479]
  3. Fundamental Research Funds for the Central Universities [30919011268]
  4. CAS Key Laboratory of Coastal Environmental Processes and Ecological Remediation (YICCAS) [2020KFJJ13]
  5. Natural Science Foundation of Guangdong Province, China [2021A1515012062]
  6. Jiangsu Shuang-chuang Project

向作者/读者索取更多资源

In this study, the UV-induced transformation of monochloro-p-benzoquinone (MCBQ) in aqueous solution was systematically investigated through quantum chemical calculations. It was found that the nucleophilic attack of OH- on carbon atoms was the central reaction, and the addition to olefinic carbon atoms was more feasible. Moreover, OH- preferred to add to the ortho-position of C-Cl bond.
In this work, the UV-induced transformation of monochloro-p-benzoquinone (MCBQ) in aqueous solution has been systematically investigated through quantum chemical calculations. During the UV irradiation at 253.7 nm, the first triplet state of MCBQ ((3)MCBQ*) was from the intersystem crossing of its first excited singlet state ((1)MCBQ*). In aqueous solution, the nucleophilic attack of OH- on carbon atoms in (3)MCBQ* was the central reaction. The addition of OH- to olefinic carbon atoms was much more kinetically feasible than that to carbonyl carbon atoms, even though the carbonyl carbon atoms were more positively charged. Moreover, OH- preferred to add to the ortho-position of C-Cl bond, where the unchlorinated atom was more negatively charged than the chlorinated one. The UV photolysis of the primary intermediate (HO-CBQ) was not the same as that of MCBQ. The attack of OH- on the para-position of C-Cl bond was the most efficient pathway. The addition of OH- to the chlorinated atom of (HO)-H-3-CBQ* was much more efficient than that in the case of (3)MCBQ*, which reveals that more UV irradiation may promote the dechlorination. The findings in the present study may be helpful to enrich the understanding of the halobenzoquinones transformation in aqueous solution.

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