New heterocyclic betaines, 4-aryl-5-(alkoxycarbonyl)-2-oxo-3-(pyridin-l-ium-l-yl)-2,3-dihydro-lH-pyrrol-3-ides, were synthesized in good yields by the reaction of alkyl 2H-azirine-2-carboxylates with 2-methoxy-2-oxo-l-(pyridin-l-ium-l-yl)ethan-l-ides, generated from the corresponding pyridinium salts. The betaines exist as the NH-tautomers both in solution and in the solid state. Two molecules of the betaine form a dimer by hydrogen bonds of the type N-H...O in solid state. According to TD DFT calculations the long-wave absorption band in betaines mainly corresponds to the intramolecular charge transfer between the negatively charged pyrrole unit and the positively charged pyridinium group. The blue shift of the long-wave absorption in protic solvents was adequately described in terms of H-complex formation with the nucleophilic centre of the molecular skeleton. (C) 2018 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)2466-2474
Number of pages9
JournalTetrahedron
Volume74
Issue number20
DOIs
StatePublished - 17 May 2018

    Research areas

  • Heterocyclic betaines, Azirines, Pyridinium ylides, Solvatochromism, MESOMERIC BETAINES, PYRIDINIUM YLIDES, DENSITY, CARBENES, EXCHANGE, SALTS, TAUTOMERIZATION, THERMOCHEMISTRY, CYCLOADDITION, DERIVATIVES

    Scopus subject areas

  • Drug Discovery
  • Biochemistry
  • Organic Chemistry

ID: 28186026