THE SELECTIVITY OF ELECTROPHILIC AROMATIC NITRATION AND THE EFFECT OF THE ORGANIC SOLVENTS

Article abstract of DOI:10.1016/S0040-4020(01)80101-0

The nitrating agent prepared by mixing Bu4NNO3 and (CF3CO)2O has been used to nitrate in homogeneous conditions eight aromatic substrates, ranging in reactivity from benzene to mesitylene, in several organic solvents.From competitive kinetic experiments and glc analysis, partial rate factors were obtained.The nature of the solvent significantly affects selectivity in the whole activation range.Selectivity was quantitatively measured by the selectivity factor for toluene, and, more properly, by the slopes in the correlations between log values of partial rate factors in a given solvent and the corresponding values in a reference solvent.Good correlations were obtained also including ortho positions and polysubstituted substrates, and the following order of relative selectivity could be established: MeNO2 < MeCN