A Molecular Balance for Measuring Aliphatic CH-π Interactions

被引：72

作者：

Carroll, William R. ^{[1
]}

Zhao, Chen ^{[1
]}

Smith, Mark D. ^{[1
]}

Pellechia, Perry J. ^{[1
]}

Shimizu, Ken D. ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 16期

基金：

美国国家科学基金会;

关键词：

FACE-TO-FACE; CH/PI INTERACTION; AROMATIC INTERACTIONS; LONE-PAIR; FLUOROAROMATIC SYSTEMS; ARENE INTERACTIONS; CRYSTAL-STRUCTURE; CONFORMATION; DATABASE; MODEL;

D O I：

10.1021/ol201657p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of conformationally flexible bicyclic N-arylimides were employed as molecular balances to study the weak aliphatic CH-pi Interaction between alkyl and arene groups. The formation of intramolecular CH-pi interactions in the folded conformers was characterized by X-ray crystallography. The strengths of the interactions were characterized in CDCl(3) by the changes in the folded/unfolded ratios, as measured by (1)H NMR. The CH-pi interaction between a methyl group and an aromatic surface was similar to 1.0 kcal/mol and was easily disrupted or masked by conformational entropy and repulsive steric Interactions.

引用

页码：4320 / 4323

页数：4

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