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• W3174879056 endingPage "117391" @default.
• W3174879056 startingPage "117391" @default.
• W3174879056 abstract "• Computational chemistry is used to predict reactivity and mechanisms of pollutants. • Reactive sites of sulfonamides for chlorination locate on 4-aminobenzenesulfonmaide. • Product identification by LTQ-Orbitrap MS verifies the in silico prediction. • k obs can be predicted by free energy barriers via the Eyring-Polanyi equation. • Sulfonamides with stronger electron-donating heterocycle is easier to be chlorinated. Increasing number of emerging pollutants in environments requires an effective approach which can facilitate the prediction of reactivity and provide insights into the reaction mechanisms. Computational chemistry is exactly the tool to fulfill this demand with its good performance in theoretical investigation of chemical reactions at molecular level. In this study, chlorination of sulfonamide antibiotics is used as an illustration to present a systematic strategy demonstrating how computational chemistry can be applied to investigate the reaction behavior of emerging pollutants. Sulfonamides is a class of micropollutants that contain the common structure of 4-aminobenzenesulfonmaide while differ in their heterocycles. Based on the calculated conceptual DFT indices, the reactive sites of sulfonamide are successfully predicted, which locate on their common structure of 4-aminobenzenesulfonmaide. Therefore, all sulfonamides follow the similar reaction pathway. Product identification by LTQ-Orbitrap MS further verifies the in silico prediction. Three critical pathways are discovered, i.e., S-N bond cleavage, Cl-substitution onto aniline-N, and the following rearrangement to lose -SO 2 - group, among which Cl-substitution is the key step due to its lowest free energy barrier. Heterocycles impact the reaction rate by affecting the electronic density of aniline group. In general, the more electron-donating the heterocycle is, the more readily sulfonamides to be chlorinated." @default.
• W3174879056 created "2021-07-05" @default.
• W3174879056 creator A5027835055 @default.
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• W3174879056 date "2021-09-01" @default.
• W3174879056 modified "2023-09-26" @default.
• W3174879056 title "Using general computational chemistry strategy to unravel the reactivity of emerging pollutants: An example of sulfonamide chlorination" @default.
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• W3174879056 doi "https://doi.org/10.1016/j.watres.2021.117391" @default.
• W3174879056 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/34233248" @default.
• W3174879056 hasPublicationYear "2021" @default.
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