期刊
CHEMICAL COMMUNICATIONS
卷 55, 期 30, 页码 4423-4426出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c9cc01402k
关键词
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资金
- Rutgers University
- NSF [CAREER CHE-1650766]
- GAIA (Rutgers University)
The structure and spectroscopic properties of the amide bond are a topic of fundamental interest in chemistry and biology. Herein, we report O-17 NMR and N-15 NMR spectroscopic data for four series of sterically-hindered acyclic amides. Despite the utility of O-17 NMR and N-15 NMR spectroscopy, these methods are severely underutilized in the experimental determination of electronic properties of the amide bond. The data demonstrate that a combined use of O-17 NMR and N-15 NMR serves as a powerful tool in assessing electronic effects of the amide bond substitution as a measure of electrophilicity of the amide bond. Notably, we demonstrate that steric destabilization of the amide bond results in electronically-activated amides that are comparable in terms of electrophilicity to acyl fluorides and carboxylic acid anhydrides.
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