PROTONATION OF 2-(2-THIENYL)PYRROLE AND 2-(2-THIENYL)-1-VINYLPYRROLES

被引：8

作者：

SIGALOV, MV ^{[1
]}

TROFIMOV, AB ^{[1
]}

SHMIDT, EY ^{[1
]}

TROFIMOV, BA ^{[1
]}

机构：

[1] IRKUTSK ORGAN CHEM INST,IRKUTSK 664033,RUSSIA

来源：

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY | 1993年 / 6卷 / 08期

关键词：

D O I：

10.1002/poc.610060805

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-(2-Thienyl)pyrrole and its 3-alkyl-1-vinyl derivatives have been shown (H-1 NMR) to be protonated by HSO3F, CF3COOH, HCl and HBr at the pyrrole C-5 atom. Reaction with the superacid system HSO3F-SbF5-SO2 results in the equilibrium between pyrrolium and thiophenium ions. The heats of formation (DELTAH), charges and HOMO partial electron densities for 2-(2-thienyl)pyrrole and its protonated forms have been calculated by the MNDO method. The calculated DELTAH values of thienylpyrrolium and pyrrolylthiophenium ions are in agreement with the experimentally observed ratio.

引用

页码：471 / 477

页数：7

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