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Updated: Sep 23, 2025

Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid
Published on: November 15, 2017
Two-electron redox chemistry of p-nitro- and p-cyanobenzene diazohydroxides
James P McEvoy1, Nhan V Pham2, Hong T Le2
1Centre for Biomedical Sciences, School of Biological Sciences, Royal Holloway University of London Egham Surrey TW20 0EX UK james.mcevoy@rhul.ac.uk.
Abstract:
The electrochemistry of aryl diazonium salts is usually dominated by one-electron reduction, loss of dinitrogen, and the grafting of aryl radicals onto the electrode. In contrast, p-nitro- and p-cyanobenzene diazonium salts dissolved in mixed aqueous-acetonitrile solvents showed diffusion-limited, quasi-reversible, two-electron cyclic voltammetry. Voltammetric pH-dependence and spectrophotometric kinetic studies suggest that the basicity and low polarity of the aqueous solvent mixture has revealed the biologically-significant interconversion of diazohydroxide and diazene.
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