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С-ОН bond cleavage initiated by electron transfer: electroreduction of 9-fluorenol Научная публикация

Журнал Electrochimica Acta
ISSN: 1873-3859 , E-ISSN: 0013-4686
Вых. Данные Год: 2016, Том: 191, Страницы: 962-973 Страниц : 12 DOI: 10.1016/j.electacta.2016.01.127
Авторы Mendkovich Andrey S. 1 , Syroeshkin Mikhail A. 1 , Nasybullina Darya V. 1 , Mikhailov Mikhail N. 1 , Gultyai Vadim P. 1 , Elinson Mikhail N. 1 , Rusakov Alexander I. 2
Организации
1 N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian Federation
2 P. G. Demidov Yaroslavl State University, 150000 Yaroslavl, Russian Federation

Реферат: Сyclic voltammetry, chronoamperometry, coulometry, electrolysis, digital simulation, quantum chemical calculations of 9-fluorenol as an example, were used to show that the electroreduction of aryl derivatives of methanol in 0.1 M Bu4NClO4/DMF proceeds via the ECE mechanism (including the stages of radical anion formation and the Csingle bondOH bond cleavage in the radical anion) complicated by the reactions of the depolarizer with the anionic products. Among these reactions are the deprotonation of 9-fluorenol and its monoanions by hydroxide anion and fluorenyl anion. The thermodynamic parameters of the reactions have been estimated both theoretically and experimentally. It was found that the equilibrium constants of the fluorenyl anions deprotonation are close (C-anion) or higher (O-anion) than that of fluorenol. As a result the total equilibrium is shifted towards the side of the dianion of 9-fluorenone. The unusual ratio of the equilibrium constants was explained by lower basicity of π*-dianion compare with other anions.
Библиографическая ссылка: Mendkovich A.S. , Syroeshkin M.A. , Nasybullina D.V. , Mikhailov M.N. , Gultyai V.P. , Elinson M.N. , Rusakov A.I.
С-ОН bond cleavage initiated by electron transfer: electroreduction of 9-fluorenol
Electrochimica Acta. 2016. V.191. P.962-973. DOI: 10.1016/j.electacta.2016.01.127 WOS Scopus OpenAlex
Идентификаторы БД:
Web of science: WOS:000371143200111
Scopus: 2-s2.0-84961309959
OpenAlex: W2317436836
Цитирование в БД:
БД Цитирований
OpenAlex 23
Web of science 20
Scopus 20
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