title: Heterocyclic ring cleavage upon collision-induced dissociation of deprotonated 3-hydroxy-1,2,5-oxadiazoles (3-hydroxyfurazans).
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.
authors.affiliation: Department of Chemistry, Dalhousie University, 6274 Coburg Road, PO Box 15000, Halifax, Nova Scotia, B3H 4R2, Canada.
authors.forename: J Stuart
authors.initials: JS
authors.lastname: Grossert
authors.affiliation: Dipartimento di Scienza e Tecnologia del Farmaco (DSTF), Università degli Studi di Torino, via Pietro Giuria 9, 10125, Torino, Italy.
authors.forename: Agnese C
authors.initials: AC
authors.lastname: Pippione
authors.affiliation: Dipartimento di Scienza e Tecnologia del Farmaco (DSTF), Università degli Studi di Torino, via Pietro Giuria 9, 10125, Torino, Italy.
authors.forename: Donatella
authors.initials: D
authors.lastname: Boschi
authors.affiliation: Dipartimento di Scienza e Tecnologia del Farmaco (DSTF), Università degli Studi di Torino, via Pietro Giuria 9, 10125, Torino, Italy.
authors.forename: Marco L
authors.initials: ML
authors.lastname: Lolli
authors.affiliation: Department of Chemistry, Dalhousie University, 6274 Coburg Road, PO Box 15000, Halifax, Nova Scotia, B3H 4R2, Canada.
authors.forename: Robert L
authors.initials: RL
authors.lastname: White
mesh_terms: D013058:Mass Spectrometry; D008958:Models, Molecular; D010069:Oxadiazoles / Q000032:analysis* / Q000737:chemistry*; D011522:Protons
chemical_list: D010069:Oxadiazoles; D011522:Protons
keywords: 3-hydroxyfurazan; computations; fragmentation mechanisms; heterocycles; negative ion; tandem mass spectrometry