REACTIONS OF RADICAL CATIONS OF METHYLATED BENZENE-DERIVATIVES IN AQUEOUS-SOLUTION

The radical cations of methylated benzene decompose in acid solution into the corresponding methylbenzyl radical and a proton. The rate constant for this reaction decreases by three orders of magnitude as the number of methyl groups increases from one to five. The rate constants can be correlated with the ionization potential of the parent compound. In neutral solution the reverse reaction to the acid-catalyzed OH adduct conversion occurs and the radical cations react with water to form the OH adduct. In slightly alkaline solution the radical cations of the higher methylated benzenes (n ≥ 3) react with hydroxide ions forming the OH adduct. © 1978 American Chemical Society.