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DOI: 10.1002/chem.201103446 Pathway of Oxygen Incorporation from O2 in TiO2 Photocatalytic Hydroxylation of Aromatics: Oxygen Isotope Labeling Studies Yue Li, Bo Wen, Cailan Yu, Chuncheng Chen,* Hongwei Ji, Wanhong Ma, and Jincai Zhao[a] Abstract: The hydroxylation process is it decreases with the increase of sub- products of strongly adsorbed benzoic the primary, and even the rate-deter- strate concentration. More intriguingly, acid (ca. 30 %) is much less than in mining step of the photocatalytic deg- when photogenerated valence-band that of weakly adsorbed benzene radation of aromatic compounds. To holes (hvb + ) are removed, nearly all the (phenol) (60 %). Such dependences make clear the hydroxylation pathway O atoms (97 %) in the hydroxyl provide unique clues to uncover the of aromatics, the TiO2 photocatalytic groups of the hydroxylated products of photocatalytic hydroxylation pathway. hydroxylation of several model sub- benzoic acid come from O2, whereas Our experiments show that the main strates, such as benzoic acid, benzene, the scavenging of conduction-band O2-incorporation pathway involves the nitrobenzene, and benzonitrile, has electrons (ecb) makes almost all the reduction of O2 by ecb and the subse- been studied by an oxygen-isotope-la- hydroxyl O atoms ( 95 %) originate quent formation of free COH via H O ,