Theoretical and experimental NMR study of protopine hydrochloride isomers

Magn Reson Chem. 2005 Jul;43(7):578-81. doi: 10.1002/mrc.1596.

Abstract

The 1H and 13C NMR chemical shifts of cis- and trans-protopinium salts were measured and calculated. The calculations of the chemical shifts consisted of conformational analysis, geometry optimization (RHF/6-31G** method) and shielding constants calculations (B3LYP/6-31G** method). Based on the results of the quantum chemical calculations, two sets of experimental chemical shifts were assigned to the particular isomers. According to the experimental results, the trans-isomer is more stable and its population is approximately 68%.

Publication types

  • Comparative Study
  • Evaluation Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzophenanthridines
  • Berberine Alkaloids / analysis*
  • Berberine Alkaloids / chemistry*
  • Carbon Isotopes
  • Computer Simulation
  • Isomerism
  • Magnetic Resonance Spectroscopy / methods*
  • Models, Chemical*
  • Models, Molecular*
  • Molecular Conformation
  • Protons

Substances

  • Benzophenanthridines
  • Berberine Alkaloids
  • Carbon Isotopes
  • Protons
  • protopine