title: In situ NMR spectroelectrochemistry for the structure elucidation of unstable intermediate metabolites.
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 (1)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.
authors.affiliation: CNRS, Chimie et Interdisciplinarité: Synthèse, Analyse et Modélisation (CEISAM), UMR 6230, LUNAM Université de Nantes, 2 rue de la Houssinière, BP 92208, 44322, Nantes Cedex 3, France.
authors.forename: Ugo
authors.initials: U
authors.lastname: Bussy
authors.forename: Patrick
authors.initials: P
authors.lastname: Giraudeau
authors.forename: Virginie
authors.initials: V
authors.lastname: Silvestre
authors.forename: Titouan
authors.initials: T
authors.lastname: Jaunet-Lahary
authors.forename: Véronique
authors.initials: V
authors.lastname: Ferchaud-Roucher
authors.forename: Michel
authors.initials: M
authors.lastname: Krempf
authors.forename: Serge
authors.initials: S
authors.lastname: Akoka
authors.forename: Illa
authors.initials: I
authors.lastname: Tea
authors.forename: Mohammed
authors.initials: M
authors.lastname: Boujtita
mesh_terms: D018712:Analgesics, Non-Narcotic / Q000737:chemistry*; D004355:Drug Stability; D009682:Magnetic Resonance Spectroscopy / Q000379:methods*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010615:Phenacetin / Q000737:chemistry*
chemical_list: D018712:Analgesics, Non-Narcotic; D010615:Phenacetin