A Molecular Balance for Measuring Aliphatic CH-π Interactions
A Molecular Balance for Measuring Aliphatic CH-π Interactions
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DOI：
10.1021/ol201657p
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发表时间：
2011-08-19
期刊：
影响因子：
5.2
通讯作者：
Shimizu, Ken D.
中科院分区：
文献类型：
--
作者：
Carroll, William R.;Zhao, Chen;Shimizu, Ken D.
采用一系列构象柔性的双环n -芳酰亚胺作为分子天平，研究了烷基与芳烃之间的弱脂肪族CH-pi相互作用。用x射线晶体学表征了折叠构象中分子内CH-pi相互作用的形成。CDCl(3)中的相互作用强度通过(1)H NMR测量的折叠/未展开比率的变化来表征。甲基与芳香族表面之间的CH-pi相互作用近似于1.0 kcal/mol，容易被构象熵和排斥性空间相互作用破坏或掩盖。
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.