Abstract
Spectral data for N-methyl-2-nitroaniline correlate well with those for N,N-dimethyl-2-nitroaniline in non-hydrogen-bonding, hydrogen-bond-accepting and amphiprotic alcoholic solvents. This same pattern has been reported for N-methyl-2-nitro-p-toluidine. These results indicate that these N-methyl compounds have no hydrogen bonds with any of the solvents studied and intramolecular hydrogen bonding predominates. In the N.M.R. spectra of such amines, long-range coupling between the H5 (ring) and N-H protons is not necessarily evidence for intramolecular hydrogen bonding. +M substituents at the 4-position increase the twist of the dimethylamino and 2-nitro groups and enhance the C1 → C2 transition, an effect which follows the order of +M abilities of the 4-substituents.
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