Stereoelectronic Effect of Curved Aromatic Structures: Favoring the Unexpected endo Conformation of Benzylic-Substituted Sumanene

被引：35

作者：

Higashibayashi, Shuhei ^{[1
,2
]}

Onogi, Satoru ^{[1
,2
]}

Srivastava, Hemant Kumar ^{[3
]}

Sastry, G. Narahari ^{[3
]}

Wu, Yao-Ting ^{[4
]}

Sakurai, Hidehiro ^{[1
,2
]}

机构：

[1] Inst Mol Sci, Okazaki, Aichi 4448787, Japan

[2] Grad Univ Adv Studies, Okazaki, Aichi 4448787, Japan

[3] Indian Inst Chem Technol, Mol Modeling Grp, Hyderabad 500607, Andhra Pradesh, India

[4] Natl Cheng Kung Univ, Dept Chem, Tainan 70101, Taiwan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 28期

关键词：

conformation analysis; density functional calculations; hyperconjugation; through-bond interactions; through-space interactions; INVERSION;

D O I：

10.1002/anie.201303134

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Throwing a curve: The first example of a through-bond stereoelectronic effect for curved aromatic compounds is described for buckybowls, that is, benzylic-substituted sumanenes. Methyl- and hydroxysumanene favor the endo-R conformer because of a difference in the strength, between the conformers, of the hyperconjugation of the benzylic C-H bond with the bowl. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：7314 / 7316

页数：3

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