期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 86, 期 17, 页码 12024-12033出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c01385
关键词
-
资金
- U.S. Department of Energy, Office of Science, Basic Energy Sciences [DE-SC0018645]
- National Science Foundation [CHE-1919850]
- U.S. Department of Energy (DOE) [DE-SC0018645] Funding Source: U.S. Department of Energy (DOE)
The study investigates the impact of carbodiimide-induced geometry changes in a chemically fueled system, inspired by nucleotide-induced conformational changes in motor proteins. The results show that the efficiency, maximum concentration, and lifetime of the system are significantly influenced by steric hindrance and electronic effects of the substituents.
Nucleotide-induced conformational changes in motor proteins are key to many important cell functions. Inspired by this biological behavior, we report a simple chemically fueled system that exhibits carbodiimide-induced geometry changes. Bridging via transient anhydride formation leads to a significant reduction of the twist about the biaryl bond of substituted diphenic acids, giving a simple molecular clamp. The kinetics are welldescribed by a simple mechanism, allowing structure-property effects to be determined. The kinetic parameters can be used to derive important characteristics of the system such as the efficiencies (anhydride yields), maximum anhydride concentrations, and overall lifetimes. Transient diphenic anhydrides tolerate steric hindrance ortho to the biaryl bond but are significantly affected by electronic effects, with electron-deficient substituents giving lower yields, peak conversions, and lifetimes. The results provide useful guidelines for the design of functional systems incorporating diphenic acid units.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据