Study of through-space substituent- interactions using N-phenylimide molecular balances

被引：15

作者：

Hwang, Jungwun ^{[1
]}

Li, Ping ^{[1
]}

Vik, Erik C. ^{[1
]}

Karki, Ishwor ^{[1
]}

Shimizu, Ken D. ^{[1
]}

机构：

[1] Univ South Carolina, Dept Chem & Biochem, Columbia, SC 29208 USA

来源：

ORGANIC CHEMISTRY FRONTIERS | 2019年 / 6卷 / 08期

基金：

美国国家科学基金会;

关键词：

PI INTERACTIONS; AROMATIC STACKING; MODEL; RECOGNITION; STRENGTH; POLAR/PI; RINGS;

D O I：

10.1039/c9qo00195f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Substituent- interactions associated with aromatic stacking interactions were experimentally measured using a small N-phenylimide molecular balance model system. The direct interaction of the substituent (NH2, CH3, OH, F, Br, CF3 and NO2) with an aromatic ring was measured in the absence of the aromatic stacking interactions in solution. The measured substituent- energies were found to correlate well with the Hammett sigma(m) parameter similar to the substituent effects observed in aromatic stacking systems. The persistent electrostatic trends in substituent effects can arise from the direct electrostatic interactions between substituents and opposing -systems.

引用

页码：1266 / 1271

页数：6

共 60 条

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