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Revisiting the Electrochemical Reduction Mechanism of Nitrosobenzene in Acetonitrile. Concomitant Reactions and Voltammetric Simulation
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Revisiting the Electrochemical Reduction Mechanism of Nitrosobenzene in Acetonitrile. Concomitant Reactions and Voltammetric Simulation
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Journal Article
Revisiting the Electrochemical Reduction Mechanism of Nitrosobenzene in Acetonitrile. Concomitant Reactions and Voltammetric Simulation
2024
Overview
The electrochemical reduction mechanism of nitrosobenzene in acetonitrile was reconsidered in this work. The commonly accepted mechanism assumes that the nitrosobenzene radical anion dimerize to yield a dianion, which decompose into azoxybenzene as the reduction product. Even though this proposal is consistent with preparative experiments, it does not reproduce fully the experimental voltammetric behaviour when it is simulated. Also, It does not explain why the apparent electron number is different in the time scale of cyclic voltammetry and preparative electrolysis. To understand these discrepancies, it was proposed the intervention of reactions consuming part of the starting nitrosobenzene, which allowed to reconsider the role of alternative chemical reactions like that occurring between the anion of phenylhydroxylamine with nitrosobenzene and the hydroxyl ion with nitrosobenzene. In this framework, these concomitant reactions were additionally included in the mechanism to simulate the voltammetric behaviour at different scan rates. Thermodynamic and kinetic parameters of the extended mechanism are reported. Since in the hydroxyl ion is either product or reactive in some reaction steps, the global mechanism was deemed to occurs as a kind of loop. The electrochemical reduction of nitrosobenzene in acetonitrile yield a radical anion which dimerize and is next protonated by traces of water to yield azoxybenzene as final product. The proper simulation of the experimental voltammograms required the introduction of concomitant reactions in which deprotonated phenylhydroxylamine and hydroxide ions are involved. The overall mechanism involves loops where nitrosobenzene is consumed.
Publisher
John Wiley & Sons, Inc,Wiley-VCH
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