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Electrochemical Reduction of Substituted Anthracenes
Author(s) -
Cheng Ellen,
Sun TaChien,
Oliver Su Y.
Publication year - 1993
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.199300089
Subject(s) - chemistry , redox , electrochemistry , electron transfer , halide , hammett equation , reaction mechanism , photochemistry , one electron reduction , computational chemistry , kinetics , inorganic chemistry , reaction rate constant , organic chemistry , electrode , catalysis , physics , quantum mechanics
A systematic investigation of the electrochemical reduction of substituted anthracenes in N,N ‐dimethylformamidc has unveiled the reductive properties of the aromatic compounds. For the anthracenes with a reversible first reduction, the redox potential exhibits linearity vs a value of the Hammett equation. For anthracenes with an irreversible first reduction, the electron transfer and chemical reaction occur via either a sequential or a concerted pathway. When the irreversible first reduction occurs at a potential more negative than E 1/2 calculated from the σ value, the reaction occurs via a sequential pathway, such as for 9‐chloroanthracene. When the irreversible first reduction occurs at a potential more positive than the expected E 1/2 , the reaction occurs via a concerted mechanism of electron transfer and bond breaking, such as for 9‐chloromethylanthracenc. The displacement of the halide results in the parent polyaromatic hydrocarbons, as in dicated by the spectroelectrochemical method.