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Electron spin resonance analysis of the oxidation reactions of nitrone type spin traps with gold(III) ion

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Copyright notice:http://pubs.nrc-cnrc.gc.ca/eng/journals/copyright.html

When cyclic nitrones, such as 5,5-dimethyl-1-pyrroline-N-oxide (DMPO),###4-phenyl-5,5-dimethyl-1-pyrroline-N-oxide (PDMPO), and###3,3,5,5-tetramethyl-1-pyrroline-N-oxide (M4PO) were mixed with hydrogen###tetrachloroaurate(III), DMPOX (5,5-dimethyl-1-pyrrolid-2-one-N-oxyl)-type free radicals###appeared with the precipitation of Au(0). The reaction did not proceed with non-cyclic###nitrones, such as N-tert-butyl-α-phenyl-nitrone (PBN) and###α-(4-pyridyl-1-oxide)-N-tert-butyl-nitrone (POBN). The order of the HAuCl4 decrease was###DMPO > PDMPO > M4PO. The reaction was depressed by the addition of chloride or###hydroxide ions. 1-Hydroxy-5,5-dimethyl-1-pyrrolid-2-one (HDMPN), the precursor of###DMPOX, was also oxidized to DMPOX by HAuCl4. Every step of gold reduction from###Au(III) to Au(0) can be used for the oxidation of HDMPN to DMPOX. Based on these and###previous results, the reaction was explained by the assumed scheme consisted of the ligand###exchange interaction of AuCl4###– with >N+-O– in DMPO, the nucleophilic addition of water###molecule to DMPO, the stepwise intra-molecular transfer of three electrons from DMPO to###Au(III), and the precipitation of Au(0).

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