期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 82, 期 12, 页码 6373-6378出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b00971
关键词
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资金
- Rutgers University
- NSF-MRI grant [CHE-1229030]
- Wroclaw Center for Networking and Supercomputing [WCSS159]
Transition-metal-catalyzed activation of amide N-C(O) bonds proceeds via selective metal insertion into the carbon nitrogen amide bond. Herein, we demonstrate that Narylanilines (anilides), the first class of planar amides that have been shown to undergo selective amide N-C cross-coupling reactions, feature a significantly decreased barrier to rotation around the amide N-C(O) bond. Most significantly, we demonstrate that amide n(N) -> pi*(C=0) resonance in simple anilides can be varied by as much as 10 kcal/mol. The data have important implications for the design of N-C(O) amide cross-coupling reactions and control of the molecular conformation of anilides by resonance effects.
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