Direct assignment of positional isomers by mass spectrometry: ortho, meta and para acyl and amidyl anilines and phenols and derivatives

dc.creatorda Rocha, LW
dc.creatorSparrapan, R
dc.creatorAugusti, R
dc.creatorEberlin, MN
dc.date2004
dc.dateOCT
dc.date2014-11-20T05:19:16Z
dc.date2015-11-26T17:15:00Z
dc.date2014-11-20T05:19:16Z
dc.date2015-11-26T17:15:00Z
dc.date.accessioned2018-03-29T00:03:15Z
dc.date.available2018-03-29T00:03:15Z
dc.identifierJournal Of Mass Spectrometry. John Wiley & Sons Ltd, v. 39, n. 10, n. 1176, n. 1181, 2004.
dc.identifier1076-5174
dc.identifierWOS:000224593700010
dc.identifier10.1002/jms.704
dc.identifierhttp://www.repositorio.unicamp.br/jspui/handle/REPOSIP/62588
dc.identifierhttp://www.repositorio.unicamp.br/handle/REPOSIP/62588
dc.identifierhttp://repositorio.unicamp.br/jspui/handle/REPOSIP/62588
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/1281935
dc.descriptionA direct MS/MS method for the ortho, meta or para configuration assignment of any single molecule that forms reference ions upon ionization and dissociation is demonstrated. Gas-phase structure diagnostic ion-molecule reactions with acetonitrile are shown to distinguish the isomeric 2-, 3- and 4-hydroxybenzoyl cations and the 2- from the 3- and 4-aminobenzoyl cations. These reference ions, which display indistinguishable 15 eV collision-induced dissociation product ion mass spectra, react with acetonitrile to yield characteristic ratios of product ions, most particularly for the 2-isomers. The reactivity of the 2-benzoyl cations is the most characteristic since the ortho configuration allows for [4(+) + 2] polar cycloaddition that yields relatively stable heterocycles in N-protonated forms. Distinction of the reference isomeric 2-, 3-and 4-hydroxy- and aminobenzoyl cations permits, therefore, partially or completely, direct 'MS-only' positional assignment of either ortho, meta or para configuration for any single molecule that forms such reference ions upon ionization and dissociation. This "class-universal" method for direct MS assignment of a single positional isomer should therefore be applicable to many members of the homologous series of isomeric ortho, meta and para acyl and amidyl anilines and phenols and derivatives. Such molecules dissociate, or are likely to dissociate, after or during ionization processes to form the reference and structurally diagnostic ortho, meta or para hydroxy- or aminobenzoyl cations. Copyright (C) 2004 John Wiley Sons, Ltd.
dc.description39
dc.description10
dc.description1176
dc.description1181
dc.languageen
dc.publisherJohn Wiley & Sons Ltd
dc.publisherChichester
dc.publisherInglaterra
dc.relationJournal Of Mass Spectrometry
dc.relationJ. Mass Spectrom.
dc.rightsfechado
dc.rightshttp://olabout.wiley.com/WileyCDA/Section/id-406071.html
dc.sourceWeb of Science
dc.subjectpentaquadrupole mass spectrometry
dc.subjectacylium ions
dc.subjectcyclization reactions
dc.subjectisomer distinction
dc.subjectortho, meta and para structural assignment
dc.subjectIon-molecule Reactions
dc.subjectGas-phase
dc.subjectIon/molecule Reactions
dc.subjectCyclic Acetals
dc.subjectCycloaddition
dc.subjectCations
dc.subjectTransacetalization
dc.subjectReactivity
dc.subjectChemistry
dc.subjectPeptides
dc.titleDirect assignment of positional isomers by mass spectrometry: ortho, meta and para acyl and amidyl anilines and phenols and derivatives
dc.typeArtículos de revistas


Este ítem pertenece a la siguiente institución