The stabilities of Meisenheimer complexes. Part 15. The interactions of 2,4,6-trinitrobenzenesulphonate ions with sodium sulphite and with sodium hydroxide in water

Abstract

In the presence of aqueous sodium sulphite 2,4,6-trinitrobenzenesulphonate ions give 1 : 1 and 1 : 2 adducts by sulphite addition at unsubstituted ring positions; kinetic and equilibrium data are reported. It is shown that the initial fast reaction of 2,4,6-trinitrobenzenesulphonate ions with aqueous sodium hydroxide results in hydroxide attack at the unsubstituted 3-position, and that ionisation of the added hydroxy-group occurs. The slower addition of hydroxide at the 1-position leads to nucleophilic substitution giving picrate ions and the observation of base catalysis in this reaction is discussed.