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- Title
In situ NMR spectroelectrochemistry for the structure elucidation of unstable intermediate metabolites.
- Authors
Bussy, Ugo; Giraudeau, Patrick; Silvestre, Virginie; Jaunet-Lahary, Titouan; Ferchaud-Roucher, Véronique; Krempf, Michel; Akoka, Serge; Tea, Illa; Boujtita, Mohammed
- Abstract
In situ NMR spectroelectrochemistry is presented in this study as a useful hybrid technique for the chemical structure elucidation of unstable intermediate species. An experimental setting was designed to follow the reaction in real time during the experimental electrochemical process. The analysis of H NMR spectra recorded in situ permitted us (1) to elucidate the reaction pathway of the electrochemical oxidation of phenacetin and (2) to reveal the quinone imine as a reactive intermediate species without using any trapping reaction. Phenacetin has been considered as hepatotoxic at high therapeutic amounts, which is why it was chosen as a model to prove the applicability of the analytical method. The use of 1D and 2D NMR experiments led to the elucidation of the major species produced from the oxidation process. We demonstrated that in situ NMR spectroelectrochemistry constitutes a fast way for monitoring unstable quinone imines and elucidating their chemical structures. [Figure not available: see fulltext.]
- Subjects
NUCLEAR magnetic resonance spectroscopy; METABOLITES; ELECTROCHEMISTRY; OXIDATION; PHENACETIN
- Publication
Analytical & Bioanalytical Chemistry, 2013, Vol 405, Issue 17, p5817
- ISSN
1618-2642
- Publication type
Article
- DOI
10.1007/s00216-013-6977-z