Laser Flash Photolysis of Tolmetin: A Photoadiabatic Decarboxylation with a Triplet Carbanion as the Key Intermediate in the Photodecomposition |
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| Authors: | S Sortino J C Scaiano |
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| Institution: | Department of Chemistry, University of Ottawa, Ottawa, ON, Canada;Dipartimento di Science Chimiche, Universita' di Catania, Catania, Italy |
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| Abstract: | Abstract— The transient photochemistry of tolmetin (TM), 5-( p -toluoyl)-1-methyl-2-pyrrolyacetic acid, a drug belonging to the nonsteroidal anti-inflammatory class, has been studied in aqueous solution by using nanosecond laser flash photolysis techniques. The photoreactivity of TM is characterized by an adiabatic pathway involving a triplet carbanion as the key intermediate in the photodecarboxylation. A short-lived triplet is proposed as the precursor of this transient species. A minor channel for laser photodecomposition involving photoionization has also been identified. This latter photoprocess occurs predominantly through a biphotonic mechanism. |
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