Selective HOESY experiments for stereochemical determinations

Magn Reson Chem. 2008 Oct;46(10):939-42. doi: 10.1002/mrc.2283.

Abstract

Heteronuclear Overhauser effect spectroscopy (HOESY) is a powerful method for tracking geometrical proximities between two heteronuclei (for instance, (1)H and (13)C, as this will be the case here). The method is based on cross-relaxation arising from dipolar interactions. Sensitivity permitting, it is applied in the 2D mode yielding all spatial correlations in a single experiment. Whenever sensitivity is not sufficient, it can be applied in the one-dimensional mode by selectively inverting one particular proton. In that case, it yields, from the carbon-13 spectrum, remote spatial correlations. The method has been employed here for the discrimination between two possible E or Z isomers in a medium-size molecule.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetates / chemistry*
  • Carbon Isotopes
  • Imidazoles / chemistry*
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular / methods*
  • Reference Standards
  • Sensitivity and Specificity
  • Stereoisomerism

Substances

  • (((1,3-dibenzyl-2,5-dioxo-4-imidazolidinylidene) methyl)sulfanyl) methyl acetate
  • Acetates
  • Carbon Isotopes
  • Imidazoles