The stabilities of Meisenheimer complexes. Part 17. The reactions of 1-X-2,4,6-trinitrobenzenes with hydroxide ions in water

Abstract

Kinetic, equilibrium, and spectroscopic data are reported for the reactions of 1-X-2,4,6-trinitrobenzenes (X = NO₂, Cl, OMe, or O^–) with hydroxide ions in water at 25 °C. In each case an initial fast reaction gives the 3-hydroxyadduct and it is shown that ionisation of the added hydroxy-group occurs. Base addition at the 1-position of the substrate leading to nucleophilic displacement of X is about an order of magnitude slower than at the 3-position. There is evidence for nucleophilic displacement of the substituent X by hydroxide within the 3-hydroxy-complexes.