Protonation of 2‐(2‐thienyl)pyrrole and 2‐(2‐thienyl)‐1‐vinylpyrroles

Mark V. Sigalov; Alexander B. Trofimov; Elena Yu Shmidt; Boris A. Trofimov

doi:10.1002/poc.610060805

Protonation of 2‐(2‐thienyl)pyrrole and 2‐(2‐thienyl)‐1‐vinylpyrroles

Mark V. Sigalov, Alexander B. Trofimov, Elena Yu Shmidt, Boris A. Trofimov

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Abstract

2‐(2‐Thienyl)pyrrole and its 3‐alkyl‐1‐vinyl derivatives have been shown (¹H 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 (ΔH), charges and HOMO partial electron densities for 2‐(2‐thienyl)pyrrole and its protonated forms have been calculated by the MNDO method. The calculated ΔH values of thienylpyrrolium and pyrrolythiophenium ions are in agreement with the experimentally observed ratio.

Original language	English
Pages (from-to)	471-477
Number of pages	7
Journal	Journal of Physical Organic Chemistry
Volume	6
Issue number	8
DOIs	https://doi.org/10.1002/poc.610060805
State	Published - 1 Jan 1993
Externally published	Yes

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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title = "Protonation of 2‐(2‐thienyl)pyrrole and 2‐(2‐thienyl)‐1‐vinylpyrroles",

abstract = "2‐(2‐Thienyl)pyrrole and its 3‐alkyl‐1‐vinyl derivatives have been shown (1H 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 (ΔH), charges and HOMO partial electron densities for 2‐(2‐thienyl)pyrrole and its protonated forms have been calculated by the MNDO method. The calculated ΔH values of thienylpyrrolium and pyrrolythiophenium ions are in agreement with the experimentally observed ratio.",

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T1 - Protonation of 2‐(2‐thienyl)pyrrole and 2‐(2‐thienyl)‐1‐vinylpyrroles

AU - Sigalov, Mark V.

AU - Trofimov, Alexander B.

AU - Shmidt, Elena Yu

AU - Trofimov, Boris A.

PY - 1993/1/1

Y1 - 1993/1/1

N2 - 2‐(2‐Thienyl)pyrrole and its 3‐alkyl‐1‐vinyl derivatives have been shown (1H 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 (ΔH), charges and HOMO partial electron densities for 2‐(2‐thienyl)pyrrole and its protonated forms have been calculated by the MNDO method. The calculated ΔH values of thienylpyrrolium and pyrrolythiophenium ions are in agreement with the experimentally observed ratio.

AB - 2‐(2‐Thienyl)pyrrole and its 3‐alkyl‐1‐vinyl derivatives have been shown (1H 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 (ΔH), charges and HOMO partial electron densities for 2‐(2‐thienyl)pyrrole and its protonated forms have been calculated by the MNDO method. The calculated ΔH values of thienylpyrrolium and pyrrolythiophenium ions are in agreement with the experimentally observed ratio.

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Protonation of 2‐(2‐thienyl)pyrrole and 2‐(2‐thienyl)‐1‐vinylpyrroles

Abstract

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