PHOTOLYSIS OF SUBSTITUTED NAPHTHALENES ON SiO2 AND Al2O3 |
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| Authors: | John T.,Barbas ,Michael E.,Sigman&dagger ,A. C. Buchanan,III Eddie A.,Chevis |
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| Affiliation: | Chemistry Division, Oak Ridge National Laboratory, P.O. Box 2008, Oak Ridge, TN 37831–6100, USA |
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| Abstract: | Abstract— Photolysis of naphthalene on the surface of SiO2 under an atmosphere of air produces phthalic acid as the only major photoproduct, accounting for 49%o of the consumed naphthalene. Photolysis on Al2O3 also produces phthalic acid, in 31% yield. Photolysis of 1 -methylnaphthalene on SiO2 proceeds under similar conditions to produce 2-acetylbenzoic acid (35%) as the major photoproduct with the production of a small amount of I-naphthaldchyde (6%). 1-Cyanonaphthalene does not photooxidize under similar conditions. The presence of oxygen is necessary for the photodecomposition of naphthalene and 1-methylnaphthalene to proceed. Superoxide formed from the photolysis of naphthalene at the SiO2/air interface is readily observed by electron paramagnetic resonance spectroscopy. In the absence of naphthalene no superoxide is observed. A mechanism involving electron transfer from the S1 state of the naphthalene to O2 is proposed on the basis of these observations and related literature precedent. |
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