Phenolic antioxidants inhibit the triplet-induced transformation of anilines and sulfonamide antibiotics in aqueous solution

Recent studies have shown that dissolved organic matter (DOM) may inhibit the excited triplet-induced oxidation of several aromatic water contaminants, in particular those containing an aniline functionality. Such an inhibition was ascribed to antioxidant moieties of DOM. The present study was conducted with the aim of verifying whether well-defined antioxidants could act as inhibitors in analogy to DOM. Various substituted phenols exhibiting antioxidant character were able, at micromolar concentration, to slow down the photoinduced depletion of several anilines and sulfonamides in aerated aqueous solution containing 2-acetonaphthone as the photosensitizer. A concomitant accelerated degradation of the phenols in the presence of such contaminants was observed. This reinforces the hypothesis of reduction of oxidation intermediates of the contaminants by the phenols. Phenol (unsubstituted) was found to be a useful inhibitor even in the case of DOM-photosensitized transformations. Phenolic antioxidants are proposed as diagnostic tools to investigate the aquatic photochemistry of aromatic amines.