Theoretical study of the conformations and strain energies of [n,n]metaparacyclophanes:: Indication of stable edge-to-face and displaced face-to-face conformers for n=4

被引：42

作者：

Hong, BH ^{[1
]}

Lee, JY ^{[1
]}

Cho, SJ ^{[1
]}

Yun, SG ^{[1
]}

Kim, KS ^{[1
]}

机构：

[1] Pohang Univ Sci & Technol, Dept Chem, Ctr Superfunct Mat, Natl Creat Res Initiat, Pohang 790784, South Korea

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 64卷 / 15期

关键词：

D O I：

10.1021/jo990755s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have studied [n,n]metaparacyclophanes-model compounds exhibiting edge-to-face and displaced stacked aromatic-aromatic interactions-using semiempirical calculations for n = 2-5 and ab initio calculations for n = 2-4. For n = 2 and 3, the strain energies govern the conformational preference, while for n = 4 and 5 the aromatic-aromatic and strain energies are equally important. The 3,12-dithio[4,4]metaparacyclophanes exhibit edge-to-face aromatic-aromatic intereactions, while the [4,4]metaparacyclophanes and 2,11-dithio[4,4]metaparacyclophanes exhibit displaced stacked aromatic-aromatic interactions.

引用

页码：5661 / 5665

页数：5

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