Kinetics of Oxidative Condensation of p-Phenylenediamines with Monohydric Phenols and Naphthols

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Abstract
The reaction of N,N-dialkyl-p-benzoquinone di-imines with phenolic and naphtholic compounds has been IIlvestigated in aqueous alkaline solution in the pH range from 7.5 to 10.8, at 25°. The reactive species in this pH range are mainly the conjugate acid of di-imine and the phenoxide ion. It is proved that the electron releasing substituents increase the reactivity of phenoxide ion, while an opposite effect is shown by electron withdrawing groups. These substituent effects have been found to be additive. A steric effect is shown by ethyl and I-butyl in mela position to hydroxy group in phenolic compounds. Furthermore naphtholic compounds are about three orders of magnitude more reactive than the corresponding phenols.

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