THE INHIBITED AUTOXIDATION OF STYREN: PART IV. SOLVENT EFFECTS

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Abstract
The influence of solvents on the rate of the uninhibited oxidation of styrene can be roughly correlated with the dielectric constants of the solvents. It is suggested that the propagation reaction involves a dipolar transition state and that the magnitude of the solvent effects might be used to identify dipolar transition states in other oxidation reactions. The effect of solvents on the rate of oxidation of styrene inhibited by phenolic antioxidants is attributed to hydrogen bonding interactions between the phenolic hydroxyl group and the solvent. The magnitude of these interactions depends on the acidity of the phenol and on the degree of steric protection afforded the hydroxyl group by ortho-alkyl substituents.