The rates of ionisation of a number of p-substituted α-nitrotoluenes in water have been studied. The rates correlate with σ rather than σ–. Replacement of one of the methylene protons by bromine increases the rate of ionisation by a factor of 149. The CBr2NO2 group is not readily displaced from the benzene ring by a base, in spite of its stability.
S. P. Avery and A. R. Butler, J. Chem. Soc., Perkin Trans. 2, 1973, 1110 DOI: 10.1039/P29730001110
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