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Regioselective oxidation of tetracycline by permanganate through alternating susceptible moiety and increasing electron donating ability

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Journal of Environmental Sciences 2020年第1期32卷 281-288页

作者： Xiaohua Jiang William AJefferson Dean Song Hanyang Cheng Fengmin Li Zhimin Qiang Aiqian Zhang Huijuan Liu Jiuhui Qu College of Environmental Science and Engineering Ocean University of ChinaQingdao 266100China The State Agriculture Ministry Laboratory of Quality&Safety Risk Assessment for Tobacco Tobacco Research InstituteChinese Academy of Agricultural SciencesQingdao 266101China Key Laboratory of Drinking Water Science and Technology Research Center for Eco-Enuironmental SciencesChinese Academy of SciencesBeijing 100085China

permanganate has attracted much attention in wide range of chemistry and particularly in degradation of environmental ***,few studies have discussed the feature of regioselective reactivity of permanganate with specific moiety of the target ***,we studied the reaction between permanganate and tetracycline that is an emerging micropollutant with different species containing several electron-rich *** second-order rate constants increased from 6.0 to 9.0 and could be quantitatively modeled by considering the speciation of both reactants,yielding kTC0=11.7(mol/L)^-1 sec^-1,kTC-=35.7(mol/L)^-1 sec^-1,kTC2-=43.1(mol/L)^-1 sec^-1 for individual reaction *** products were then identified as the hydroxylated and demethylated *** result suggested a rate-limiting step of simple hydroxylation at the phenolic and/or alkene moieties,while the demethylation should be caused by the unavoidably formed manganese oxide via single electron *** is supported by the DFT calculation,indicating the primary oxidation of phenolic group of TC0 with activation barrier of 44.5 kcal/mol and of alkene group of TC-and TC2-with activation barriers of 44.0 and 43.4 kcal/mol,*** is in agreement with the experimental results,implying the alternation of regioselectivity associated with the deprotonation *** result was further supported by performing the Fukui function and electrostatic potential analysis,reflecting the more probable site and better electron donating tendency beneficial to the permanganate oxidation.

关键词： permanganate oxidation of tetracycline Regioselective reactivity Rate-limiting hydroxylation step Altered susceptible moiety Increased electronegativity

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