Heterocyclic ring cleavage upon collision-induced dissociation of deprotonated 3-hydroxy-1,2,5-oxadiazoles (3-hydroxyfurazans)

J Stuart Grossert; Agnese C Pippione; Donatella Boschi; Marco L Lolli; Robert L White

doi:10.1002/jms.3724

Heterocyclic ring cleavage upon collision-induced dissociation of deprotonated 3-hydroxy-1,2,5-oxadiazoles (3-hydroxyfurazans)

J Mass Spectrom. 2015 Dec;50(12):1433-7. doi: 10.1002/jms.3724.

Authors

J Stuart Grossert¹, Agnese C Pippione², Donatella Boschi², Marco L Lolli², Robert L White¹

Affiliations

¹ Department of Chemistry, Dalhousie University, 6274 Coburg Road, PO Box 15000, Halifax, Nova Scotia, B3H 4R2, Canada.
² Dipartimento di Scienza e Tecnologia del Farmaco (DSTF), Università degli Studi di Torino, via Pietro Giuria 9, 10125, Torino, Italy.

PMID: 26634978
DOI: 10.1002/jms.3724

Abstract

A series of 4-substituted 3-hydroxyfurazans were subjected to electrospray ionization tandem mass spectrometry. At low collision energy, oxyisocyanate ([O=C=N-O](-), m/z 58) was formed as the predominant product ion from each deprotonated 3-hydroxyfurazan, indicating cleavage of the heterocyclic ring. The facile energetics of this characteristic fragmentation process was confirmed by density functional computations.

Keywords: 3-hydroxyfurazan; computations; fragmentation mechanisms; heterocycles; negative ion; tandem mass spectrometry.

Publication types

Letter
Research Support, Non-U.S. Gov't

MeSH terms

Mass Spectrometry
Models, Molecular
Oxadiazoles / analysis*
Oxadiazoles / chemistry*
Protons

Substances

Oxadiazoles
Protons