A Molecular Balance for Measuring Aliphatic CH-π Interactions

被引：71
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
收藏
页码：4320 / 4323
页数：4
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