Ester substituted bithiophenes. Abnormally low dihedral angle and rotation barrier due to dipolar stabilization

被引：25

作者：

Pomerantz, M ^{[1
]}

Cheng, Y ^{[1
]}

机构：

[1] Univ Texas, Dept Chem & Biochem, Arlington, TX 76019 USA

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 17期

关键词：

biaryls; electrostatic effects; theoretical studies; thiophenes;

D O I：

10.1016/S0040-4039(99)00500-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ab initio calculations [3-21G((*))] on dimethyl 2.2'-bithiophene-4,4'-dicarboxylate (3), dimethyl 2,2'-bithiophene-3,4'-dicarboxylate (4) and dimethyl 2,2'-bithiophene-3,3'-dicarboxylate (5) have revealed that in 4 there is an abnormally small dihedral angle between the thiophene rings and an abnormally low barrier to rotation around the thiophene-thiophene single bond. This is due to a favorable coulombic interaction of the negative carbonyl oxygen and the positive sulfur of the adjacent ring which helps to flatten and bend the ground state and lower the rotation barrier. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：3317 / 3320

页数：4

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