Unexpected benzimidazole ring formation from a quinoneimide species in the presence of ammonium acetate as supporting electrolyte used in the coupling of electrochemistry with mass spectrometry

Rapid Communications in Mass Spectrometry : RCM
Ugo BussyMohammed Boujtita

Abstract

Electrochemistry (EC) coupled to mass spectrometry (MS) has been used to study different phase-I reactions. Despite of the versatility of EC/MS, the effect of the nature of the supporting electrolyte on the formation of oxidation products has seldom been discussed during EC/MS experiments. Here, we present a comparison of two different supporting electrolytes and their effect on the identification of unstable intermediate oxidation species is discussed. The oxidation of acebutolol was performed with a coulometric cell in the presence of two supporting electrolytes namely ammonium acetate and lithium acetate. Ultra-performance liquid chromatography/quadrupole time-of-flight mass spectrometry (UPLC/QTOFMS) using a binary gradient (water/acetonitrile) with positive electrospray ionization was used to identify the oxidation products in the presence and absence of glutathione. Chemical structure elucidations of the oxidation products were performed by high-resolution mass spectrometry (HRMS) and were also supported by nuclear magnetic resonance (NMR) measurements. From the electrochemical study and HRMS measurements, we demonstrate that the quinoneimide species resulting from the oxidative hydrolyses of acebutolol gives a benzimidaz...Continue Reading

References

Apr 3, 2003·Rapid Communications in Mass Spectrometry : RCM·Ulrik JurvaAndries P Bruins
Aug 12, 2004·The Journal of Chemical Physics·A Daniel Boese, Jan M L Martin
Jun 19, 2007·Rapid Communications in Mass Spectrometry : RCM·Tove JohanssonUlrik Jurva
Jul 3, 2007·Journal of Mass Spectrometry : JMS·Karsten LevsenArnd Ingendoh
Dec 29, 2007·Analytical and Bioanalytical Chemistry·Wiebke Lohmann, Uwe Karst
Oct 10, 2008·Journal of the American Society for Mass Spectrometry·Wiebke LohmannUwe Karst
Nov 17, 2009·Analytical Chemistry·Sabrina KlodLothar Dunsch
Mar 15, 2011·Current Drug Metabolism·Eslam Nouri-NigjehHjalmar P Permentier
May 16, 2013·Analytical and Bioanalytical Chemistry·Ugo BussyMohammed Boujtita
Oct 7, 2014·Chemical Research in Toxicology·Ugo Bussy, Mohammed Boujtita

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