The stabilities of Meisenheimer complexes. Part 22. The ionisation of 2,4-dinitroaniline, its N-alkylated derivatives, and 2,6-dinitroaniline in methanol–dimethyl sulphoxide containing sodium methoxide
- 1 January 1980
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 12,p. 1854-1858
- https://doi.org/10.1039/p29800001854
Abstract
2,4-Dinitroaniline and its N-alkylated derivatives react with sodium methoxide in methanol–dimethyl sulphoxide to give the conjugate base. However, in the case of 2,6-dinitroaniline, base addition at the 3-position competes with proton loss. The effects of N-alkylation on the acidity of 2,4-dinitroaniline are considered and are compared with the effects of similar substitution in 2,4,6-trinitroaniline.Keywords
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