Abstract
The oxidation of meta- and para-substituted anilines by Cr VI oxidant, imidazolium fluorochromate (IFC), in aqueous acetic acid mixtures of varying compositions in the presence of p-toluenesulfonic acid (PTS) is first order in IFC and PTS. Michaelis-Menten type kinetics is observed with all of the anilines. The IFC oxidation of 15 meta- and para-substituted anilines at 299-322 K complies with the isokinetic relationship but not to any of the linear free energy relationships. The isokinetic temperature lies within the experimental range. The rate data failed to correlate with macroscopic solvent parameters such as relative permittivity, e r , and ionizing power, Y, correlation of rate data with Kamlet-Taft solvatochromic parameters (hydrogen bond donor acidity, α, hydrogen bond acceptor basicity, β. and dipolarity/polarizability, π * ) is linear which suggests that the specific solute-solvent interactions play a dominating role in governing the reactivity.
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