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dc.contributor.CRUESPUniversidade Estadual de Campinaspt_BR
dc.typeArtigo de periódicopt_BR
dc.titleKetalization of gaseous acylium ionspt_BR
dc.contributor.authorMoraes, LABpt_BR
dc.contributor.authorEberlin, MNpt_BR
unicamp.authorUniv Estadual Campinas, Inst Chem, BR-13083970 Campinas, SP, Brazilpt_BR
dc.subject.wosDistonic Radical Cationspt_BR
dc.subject.wosGas-phase Reactionspt_BR
dc.subject.wosMolecule Reactionspt_BR
dc.subject.wosMass-spectrometrypt_BR
dc.subject.wosDimethylchlorinium Ionpt_BR
dc.subject.wosCharged Electrophilespt_BR
dc.subject.wosMethoxymethyl Cationpt_BR
dc.subject.wosCyclic Acetalspt_BR
dc.subject.wosSubstitutionpt_BR
dc.subject.wosAlcoholspt_BR
dc.description.abstractA novel reaction of gaseous acylium ions: ketalization with diols and analogs, has been systematically studied via pentaquadrupole MS2 and MS3 experiments and ab initio calculations. A variety of alpha,beta -diols and their amino, thiol, ether, and thioether analogs have been tested for reactivity, mechanism evaluation, site selectivity, and for the effects of alpha- and beta -interfunctional separation. As for condensed-phase ketalization of neutral carbonyl compounds followed by hydrolysis, gaseous acylium ions are chemically deactivated in the form of cyclic ionic ketals by ketalization, and are efficiently released via on-line collision-induced dissociation. Ketalization of acylium ions is shown to identify and structurally characterize alpha,beta -diols and their analogs, and to distinguish regioisomers. Diastereomers can also be distinguished, as illustrated for cis and trans 1,2-diaminocyclohexane. The MS2 and MS3 data together with O-18-labeling and ab initio calculations establish for acylium ion ketalization a mechanism of anchimeric assistance with participation of the neighboring acyl group. (C) 2001 American Society for Mass Spectrometry.pt
dc.relation.ispartofJournal Of The American Society For Mass Spectrometrypt_BR
dc.relation.ispartofabbreviationJ. Am. Soc. Mass Spectrom.pt_BR
dc.publisher.cityNew Yorkpt_BR
dc.publisher.countryEUApt_BR
dc.publisherElsevier Science Incpt_BR
dc.date.issued2001pt_BR
dc.date.monthofcirculationFEBpt_BR
dc.identifier.citationJournal Of The American Society For Mass Spectrometry. Elsevier Science Inc, v. 12, n. 2, n. 150, n. 162, 2001.pt_BR
dc.language.isoenpt_BR
dc.description.volume12pt_BR
dc.description.issuenumber2pt_BR
dc.description.firstpage150pt_BR
dc.description.lastpage162pt_BR
dc.rightsfechadopt_BR
dc.rights.licensehttp://www.elsevier.com/about/open-access/open-access-policies/article-posting-policypt_BR
dc.sourceWeb of Sciencept_BR
dc.identifier.issn1044-0305pt_BR
dc.identifier.wosidWOS:000166818700003pt_BR
dc.identifier.doi10.1016/S1044-0305(00)00211-7pt_BR
dc.date.available2014-11-16T09:11:25Z
dc.date.available2015-11-26T16:21:28Z-
dc.date.accessioned2014-11-16T09:11:25Z
dc.date.accessioned2015-11-26T16:21:28Z-
dc.description.provenanceMade available in DSpace on 2014-11-16T09:11:25Z (GMT). No. of bitstreams: 1 WOS000166818700003.pdf: 425827 bytes, checksum: 8e90b851cf183a3835abe182321ff793 (MD5) Previous issue date: 2001en
dc.description.provenanceMade available in DSpace on 2015-11-26T16:21:28Z (GMT). No. of bitstreams: 2 WOS000166818700003.pdf: 425827 bytes, checksum: 8e90b851cf183a3835abe182321ff793 (MD5) WOS000166818700003.pdf.txt: 42321 bytes, checksum: 5ff3193d0512721feb3d7d2e66d6409c (MD5) Previous issue date: 2001en
dc.identifier.urihttp://www.repositorio.unicamp.br/jspui/handle/REPOSIP/60940pt_BR
dc.identifier.urihttp://www.repositorio.unicamp.br/handle/REPOSIP/60940
dc.identifier.urihttp://repositorio.unicamp.br/jspui/handle/REPOSIP/60940-
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