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Quantum Chemistry Study on the Reaction Mechanism of Ozone Oxidation of Benzothiophene and Its Derivatives
Received date: 2015-12-20
Revised date: 2016-03-10
Online published: 2016-04-29
A theoretical study on the geometries, reaction paths, as well as the frontier molecular orbitals of the ozone oxidation of benzothiophene and its derivatives was conducted by using the density functional theory B3LYP method at 6-31G* and 6-311++G(d, p) levels. Firstly, ozone attack on the double bond of benzothiophene (BT). The highest occupied molecular orbital (HOMO) of the ozone and the lowest unoccupied molecular orbital (LUMO) of benzothiophene are symmetrical matched each other to generate a complex. Finally, 2-mercapto-benzoic acid was produced by breaking the double five-membered ring. Furthermore, the ozonation of dibenzothiophene (DBT) and 4,6-dimethyldibenzothiophene (4,6-DMDBT) are calculated. The sulfides were oxidized to sulfoxide, and further oxidized to sulfone. Based on the activation energies, the reactivity of benzothiophene and its derivatives to ozone are in the following order: BT > 4,6-DMDBT > DBT.
Key words: ozone oxidation; benzothiophene; reaction mechanism; oxidation activity; DFT
JIANG Min-jie , WANG Han-lu , LIANG Wei , ZHOU Jian-Min . Quantum Chemistry Study on the Reaction Mechanism of Ozone Oxidation of Benzothiophene and Its Derivatives[J]. Advances in New and Renewable Energy, 2016 , 4(2) : 139 -145 . DOI: 10.3969/j.issn.2095-560X.2016.02.0010
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