期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 78, 期 12, 页码 6344-6349出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo400944r
关键词
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资金
- Chemical Sciences, Geo-sciences, and Biosciences Division, Office of Basic Energy Sciences, Early Career Research Program of the U.S.
- Department of Energy [DE-SC0006518, DE-FG02-11ER16239]
- University of Pennsylvania
- U.S. National Science Foundation [CHE-0131132, OCI-1053575]
- XSEDE
- U.S. Department of Energy (DOE) [DE-SC0006518] Funding Source: U.S. Department of Energy (DOE)
N-tert-Butyl-N-2-pyridylhydroxylamines were synthesized from 2-halopyridines and 2-methyl-2-nitrosopropane using magnesium halogen exchange. The use of Turbo Grignard generated the metallo-2-pyridyl intermediate more reliably than alkyllithium reagents. The hydroxylamines were characterized using NMR, electrochemistry, and density functional theory. Substitution of the pyridyl ring in the 3-, 4-, and 5-positions was used to vary the potential of the nitroxyl/oxoammonium redox couple by 0.95 V. DFT computations of the electrochemical properties agree with experiment and provide a toolset for the predictive design of pyridyl nitroxides.
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