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

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

Research output: Contribution to journalArticlepeer-review

8 Scopus citations

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 languageEnglish
Pages (from-to)471-477
Number of pages7
JournalJournal of Physical Organic Chemistry
Volume6
Issue number8
DOIs
StatePublished - 1 Jan 1993
Externally publishedYes

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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