Benzoquinone imines. Part II. Hydrolysis of p-benzoquinone monoimine and p-benzoquinone di-imine
- 1 January 1969
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society B: Physical Organic
- p. 213-216
- https://doi.org/10.1039/j29690000213
Abstract
Kinetic studies of the hydrolysis of p-benzoquinone monoimine, over the pH range 2–10, have shown that the reaction exhibits first-order kinetics over the whole pH range. The pH dependence indicates a rate-controlling step involving the reaction of both the free imine and its protonated form with water, the latter being 1·8 × 103 more reactive than the former. The reaction was found to be catalysed by phosphate ions. Similarly the hydrolysis of p-benzoquinone di-imine involves reaction of the free base and its mono- and di-protonated forms with water. Phosphate ions do not catalyse the reaction, but, in the pH range 5·5–8, polymerisation of the di-imine occurs as a significant side-reaction, even at low concentrations.Keywords
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