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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.wosDimethylchlorinium Ionpt_BR
dc.subject.wosCharged Electrophilespt_BR
dc.subject.wosMethoxymethyl Cationpt_BR
dc.subject.wosCyclic Acetalspt_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
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.publisherElsevier Science Incpt_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.sourceWeb of Sciencept_BR
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