Electrochemical reduction, radical anions, and dehalogenation of fluorinated/chlorinated 2,1,3-benzothia/selenadiazoles

Leonid A. Shundrin, Irina G. Irtegova, Pavel A. Avrorov, Tatiana F. Mikhailovskaya, Arkady G. Makarov, Alexander Yu Makarov, Andrey V. Zibarev

Результат исследования: Научные публикации в периодических изданияхстатья

2 Цитирования (Scopus)

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 оригиналаанглийский
Страницы (с-по)166-180
Число страниц15
ЖурналArkivoc
Том2017
Номер выпуска3
DOI
СостояниеОпубликовано - 25 июн 2017

Fingerprint Подробные сведения о темах исследования «Electrochemical reduction, radical anions, and dehalogenation of fluorinated/chlorinated 2,1,3-benzothia/selenadiazoles». Вместе они формируют уникальный семантический отпечаток (fingerprint).

Цитировать