Issue 4, 1978

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.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1978, 343-346

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

M. R. Crampton, J. Chem. Soc., Perkin Trans. 2, 1978, 343 DOI: 10.1039/P29780000343

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