Protonated forms of 2-(2-thienyl)pyrroles. Investigation by means of 1H NMR spectroscopy and MNDO calculations

M. V. Sigalov; A. B. Trofimov; E. Yu Shmidt; B. A. Trofimov

doi:10.1007/BF00531554

Protonated forms of 2-(2-thienyl)pyrroles. Investigation by means of ¹H NMR spectroscopy and MNDO calculations

M. V. Sigalov, A. B. Trofimov, E. Yu Shmidt, B. A. Trofimov

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Abstract

By means of ₁H NMR spectroscopy it was demonstrated that 2-(2-thienyl)pyrrole and its 1-vinyl-substituted derivatives are protonated by adds (HSO₃F, CF₃CO₂H, HCl, and HBr) at the C₅ atom of the pyrrole ring. The reaction with the superacid system HSO₃F/SbF₅/SO₂ leads to an equilibrium mixture of pyrrolium and thiophenium ions. The MNDO method was used to calculate the heats of formation (δH), charges, and partial electron densities of the highest occupied molecular orbitals (HOMO) of 2-(2-thienyl)pyrrole and its protonated forms. The calculated δH values of the thienylpyrrolium and pyrrolylthiophenium ions are in agreement with the experimentally established relationship.

Original language	English
Pages (from-to)	711-719
Number of pages	9
Journal	Chemistry of Heterocyclic Compounds
Volume	29
Issue number	6
DOIs	https://doi.org/10.1007/BF00531554
State	Published - 1 Jun 1993
Externally published	Yes

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Organic Chemistry

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title = "Protonated forms of 2-(2-thienyl)pyrroles. Investigation by means of 1H NMR spectroscopy and MNDO calculations",

abstract = "By means of 1H NMR spectroscopy it was demonstrated that 2-(2-thienyl)pyrrole and its 1-vinyl-substituted derivatives are protonated by adds (HSO3F, CF3CO2H, HCl, and HBr) at the C5 atom of the pyrrole ring. The reaction with the superacid system HSO3F/SbF5/SO2 leads to an equilibrium mixture of pyrrolium and thiophenium ions. The MNDO method was used to calculate the heats of formation (δH), charges, and partial electron densities of the highest occupied molecular orbitals (HOMO) of 2-(2-thienyl)pyrrole and its protonated forms. The calculated δH values of the thienylpyrrolium and pyrrolylthiophenium ions are in agreement with the experimentally established relationship.",

author = "Sigalov, {M. V.} and Trofimov, {A. B.} and Shmidt, {E. Yu} and Trofimov, {B. A.}",

year = "1993",

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T1 - Protonated forms of 2-(2-thienyl)pyrroles. Investigation by means of 1H NMR spectroscopy and MNDO calculations

AU - Sigalov, M. V.

AU - Trofimov, A. B.

AU - Shmidt, E. Yu

AU - Trofimov, B. A.

PY - 1993/6/1

Y1 - 1993/6/1

N2 - By means of 1H NMR spectroscopy it was demonstrated that 2-(2-thienyl)pyrrole and its 1-vinyl-substituted derivatives are protonated by adds (HSO3F, CF3CO2H, HCl, and HBr) at the C5 atom of the pyrrole ring. The reaction with the superacid system HSO3F/SbF5/SO2 leads to an equilibrium mixture of pyrrolium and thiophenium ions. The MNDO method was used to calculate the heats of formation (δH), charges, and partial electron densities of the highest occupied molecular orbitals (HOMO) of 2-(2-thienyl)pyrrole and its protonated forms. The calculated δH values of the thienylpyrrolium and pyrrolylthiophenium ions are in agreement with the experimentally established relationship.

AB - By means of 1H NMR spectroscopy it was demonstrated that 2-(2-thienyl)pyrrole and its 1-vinyl-substituted derivatives are protonated by adds (HSO3F, CF3CO2H, HCl, and HBr) at the C5 atom of the pyrrole ring. The reaction with the superacid system HSO3F/SbF5/SO2 leads to an equilibrium mixture of pyrrolium and thiophenium ions. The MNDO method was used to calculate the heats of formation (δH), charges, and partial electron densities of the highest occupied molecular orbitals (HOMO) of 2-(2-thienyl)pyrrole and its protonated forms. The calculated δH values of the thienylpyrrolium and pyrrolylthiophenium ions are in agreement with the experimentally established relationship.

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Protonated forms of 2-(2-thienyl)pyrroles. Investigation by means of ¹H NMR spectroscopy and MNDO calculations

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