title: Voltammetry coupled to mass spectrometry in the presence of isotope 18O labeled water for the prediction of oxidative transformation pathways of activated aromatic ethers: acebutolol.
abstract: The coupling between an electrochemical cell (EC) and a mass spectrometer (MS) is a useful screening tool (EC-MS) to study the oxidative transformation pathways of various electroactive species. For that purpose, we showed that the EC-MS method, carried out in the presence and absence of isotope (18)O labeled water leads not only to a fast identification of oxidation products but also leads to a fast elucidation of the mechanism pathway reaction. We examined herein the case of the electrochemical hydrolysis of activated aromatic ether. Acebutolol (β-blockers) was selected herein as model of activated aromatic ether, and its electrochemical oxidation was examined in both the presence and absence of isotope (18)O labeled water. To elucidate electrochemical hydrolysis pathway reaction: O-dealkylation or O-dealkoxylation, our approach was used to prove its applicability. The electrochemical oxidation mechanism was then elucidated showing an O-dealkoxylation reaction. In addition, density functional theory (DFT) calculations fully support the experimental conclusions.
authors: LUNAM Université de Nantes, CNRS, Chimie et Interdisciplinarité: Synthèse, Analyse et Modélisation (CEISAM), UMR 6230, Nantes, France.
authors: Ugo
authors: U
authors: Bussy
authors: Illa
authors: I
authors: Tea
authors: Véronique
authors: V
authors: Ferchaud-Roucher
authors: Michel
authors: M
authors: Krempf
authors: Virginie
authors: V
authors: Silvestre
authors: Nicolas
authors: N
authors: Galland
authors: Denis
authors: D
authors: Jacquemin
authors: Moa
authors: M
authors: Andresen-Bergström
authors: Ulrik
authors: U
authors: Jurva
authors: Mohammed
authors: M
authors: Boujtita