The anodic oxidation of 1,4-diaminobenzene: an electron spin resonance and electrochemical study
Abstract
The electrochemical e.s.r. of 1,4-diaminobenzene, 1,4-diamino-2-chlorobenzene, and 1,4-diamino-2-methyl-benzene has been studied in aqueous methanol using an apparatus in which a tube electrode is linked to the e.s.r. cavity. Laminar flow transports species from the electrode into the cavity. The distribution of species in the cavity can be described theoretically and from the variation of e.s.r. signal with current, flow rate, concentration, and pH the protonation and kinetic stability of the 1,4-diaminobenzene cation radical is established. From the electrochemistry, the protonation of the unstable benzoquinone di-imide is deduced. The kinetics and the mechanism of its substitution reaction with water leading to benzoquinone are deduced from the behaviour of the e.s.r. signal from the radical cation with which the benzoquinone di-imide is in equilibrium.
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