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Chemistry of Heterocyclic Compounds

, Volume 15, Issue 4, pp 394–400 | Cite as

13C NMR spectra of the bases and conjugate acids of 3- and 5-formyl-,acetyl-, and carbethoxypyrroles

  • M. I. Struchkova
  • G. G. Dvoryantseva
  • R. P. Evstigneeva
Article

Abstract

The effect of protonation of the oxygen atom of the carbonyl group and the carbon atom of the pyrrole ring on the 13C chemical shifts in a series of 3- and 5-formyl-, 3-acetyl-, and 3-carbethoxypyrroles was studied. The structures of the conjugate acids of the 5-carbethoxypyrroles was established on the basis of measurement of the 1H and 13C NMR spectra. It is shown that protonation of the 5-carbethoxypyr roles occurs at the ring 5-C atom in 28–35 N H2SO4. The effect of structural factors and the acidity of the medium on the relative stabilities of the CH conjugate acids of the investigated compounds is examined.

Keywords

Oxygen Organic Chemistry Acidity Carbonyl Carbon Atom 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Plenum Publishing Corporation 1979

Authors and Affiliations

  • M. I. Struchkova
    • 1
    • 2
    • 3
  • G. G. Dvoryantseva
    • 1
    • 2
    • 3
  • R. P. Evstigneeva
    • 1
    • 2
    • 3
  1. 1.N. D. Zelinskii Institute of Organic ChemistryAcademy of Sciences of the USSRMoscow
  2. 2.M. V. Lomonosov Moscow Institute of Fine Chemical TechnologyMoscow
  3. 3.S. Ordzhonikidze All-Union Scientific-Research Pharmaceutical-Chemical InstituteMoscow

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