The stabilities of Meisenheimer complexes. Part 17. The reactions of 1-X-2,4,6-trinitrobenzenes with hydroxide ions in water
- 1 January 1979
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 5,p. 648-652
- https://doi.org/10.1039/p29790000648
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.Keywords
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