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A study on the mechanism of reaction between BNAH and chloranil: Evidence for electron transfer
Author(s) -
Gao ZhongLi,
Zhang MinBao,
Liu YouCheng
Publication year - 1992
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.19920100208
Subject(s) - chemistry , chloranil , electron transfer , photochemistry , hydride , benzene , reaction mechanism , ion , computational chemistry , organic chemistry , catalysis , hydrogen
The reaction between chloranil and N −benzyldihydronicotinamide (BNAH) in borate buffer/DMF was investigated. The reaction mixture gave a strong esr signal, which is consistent with that of chloranil anion radical, and tetrachlorohydrophenol (QH 2 ) and N −benzylnicotinamide (BNA + ) were obtained as the sole products. When the reaction was run in benzene solution, a green coloured charge‐transfer complex between the reactants could be isolated, which decomposed in polar solvents to give BNA + and QH 2 . Based on kinetic studies by esr spectroscopy by the stopped‐flow technique, a two‐step electron‐transfer mechanism for the reaction is proposed in contrast to the hydride‐transfer mechanism reported in the literature.