Аннотация
At the first stage of electrochemical reduction in DMF, fluorinated/chlorinated 2,1,3-benzothia/selenadiazoles formed long-lived radical anions characterized by EPR and DFT. Gas-phase electron affinities (EA1) from DFT correlated well with the first-peak potentials separately for S and Se derivatives, and the latter were found to be better electron acceptors than the former in contrast to the atomic EA1 and Allen electronegativity. At the second stage, chalcogen-and halogen-dependent dehalogenation proceeded: non-hydrodefluorination of selenadiazoles through their n-electron activation (n ≥ 2), and hydrodechlorination of thia/selenadiazoles through H+ addition to their dianions. These differ from dehalogenation of related (aza) aromatics (e.g. benzenes, naphthalenes, quinoxalines).
Язык оригинала | английский |
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Страницы (с-по) | 166-180 |
Число страниц | 15 |
Журнал | Arkivoc |
Том | 2017 |
Номер выпуска | 3 |
DOI | |
Состояние | Опубликовано - 25 июн 2017 |