Unexpected hydrodefluorination of 3-Cl-tetrafluoropyridine. Interpretation through analysis of the potential energy surface for its radical anion

Journal of Fluorine Chemistry(2020)

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摘要
•3-chloro-tetrafluoropyridine radical anion decay was investigated theoretically.•Solvation effects are capable to affect the dehalogenation channel ratio.•What C-Hal bond will be broken depends on its position in pyridine ring.•The energy preference of Cl− elimination vs. the low barrier for F− elimination.•3-chloro-tetrafluoropyridine hydrodehalogenation - thermodynamics vs. kinetics.
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关键词
Reductive dehalogenation,Reaction mechanism,Mixed fluoro-chloro-pyridines,Intermediate radical anions,Solvent reorganization,Potential energy surface sections
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