期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 134, 期 1, 页码 138-141出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja209570y
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资金
- CNPq
- INCT-Catalise
- CAPES
- FAPESC
- Office of Naval Research [N0014-09-1-0217]
The reaction mechanism of the GPx-like oxidation of PhSH with H2O2 catalyzed by selenoxides proceeds via formation of the hydroxy perhydroxy selenane, which is a stronger oxidizing agent than selenoxide. A hydroxy perhydroxy selenane intermediate was observed by electrospray ionization mass spectrometry and Se-77 NMR spectroscopy in reactions of selenoxide 8 with H2O2. The initial velocity of oxidation of PhSH by H2O2 with selenoxide 8 is 4 orders of magnitude higher than that of 8 without peroxide. Selenoxide 8 is not reduced to selenide 6 by PhSH in the presence of H2O2. While electronic substituent effects have minimal impact on the catalytic performance of selenoxides, chelating groups increase the rate of catalysis.
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