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dc.contributor.CRUESPUniversidade Estadual de Campinaspt_BR
dc.typeArtigo de periódicopt_BR
dc.titleThe preferred all-gauche conformations in 3-fluoro-1,2-propanediolpt_BR
dc.contributor.authorAndrade, LAFpt_BR
dc.contributor.authorSilla, JMpt_BR
dc.contributor.authorDuarte, CJpt_BR
dc.contributor.authorRittner, Rpt_BR
dc.contributor.authorFreitas, MPpt_BR
unicamp.author.emailmatheus@dqi.ufla.brpt_BR
unicamp.authorAndrade, Laize A. F. Silla, Josue M. Freitas, Matheus P. Univ Fed Lavras, Dept Chem, Lavras, Brazilpt_BR
unicamp.authorDuarte, Claudimar J. Rittner, Roberto Univ Estadual Campinas, Inst Chem, BR-13083970 Campinas, SP, Brazilpt_BR
dc.subject.wosHydrogen-bondpt_BR
dc.subject.wosDensitypt_BR
dc.subject.wos2-fluoroethanolpt_BR
dc.subject.wosExchangept_BR
dc.subject.wosBehaviorpt_BR
dc.description.abstractA competition between the terminal fluorine and hydroxyl groups by the central hydroxyl group as hydrogen bond donor in 3-fluoro-1,2-propanediol would be expected to dictate the conformational isomerism of this compound, but also the repulsion between the electronegative and bulky vicinal substituents. Indeed, an intramolecular hydrogen bond has been verified only for a local minimum using QTAIM calculations, while the most stable conformer exhibits an all-gauche conformation with a small stabilizing contribution from the n(F)->sigma(star)(OH) interaction. The preferred orientation of the OH and F substituents was confirmed from the chemical shifts and coupling constants of the diastereotopic hydrogens. This conformational preference, which is calculated to exist both in the gas phase and solution (using implicit CHCl3 and CH3CN solvents), is better described by predominant hyperconjugative interactions over Lewis-type interactions. The strong contribution from antiperiplanar interactions involving sigma(CH) and sigma(CC) as electron donors and sigma(star)(CF) and sigma CO star as electron acceptors dictates the gauche effect in 3-fluoro-1,2-propanediol rather than a hydrogen bond. The absence of J(F,H(O)) and J(H(O)),(H(O)) coupling constants confirms that any influence from a hydrogen bond to the conformational isomerism of 3-fluoro1,2-propanediol is secondary.pt
dc.description.noteo TEXTO COMPLETO DESTE ARTIGO, ESTARÁ DISPONÍVEL À PARTIR DE AGOSTO DE 2015.pt
dc.relation.ispartofOrganic & Biomolecular Chemistrypt_BR
dc.relation.ispartofabbreviationOrg. Biomol. Chem.pt_BR
dc.publisher.cityCambridgept_BR
dc.publisher.countryInglaterrapt_BR
dc.publisherRoyal Soc Chemistrypt_BR
dc.date.issued2013pt_BR
dc.date.monthofcirculationOCT 21pt_BR
dc.identifier.citationOrganic & Biomolecular Chemistry. Royal Soc Chemistry, v. 11, n. 39, n. 6766, n. 6771, 2013.pt_BR
dc.language.isoenpt_BR
dc.description.volume11pt_BR
dc.description.issuenumber39pt_BR
dc.description.firstpage6766pt_BR
dc.description.lastpage6771pt_BR
dc.rightsembargopt_BR
dc.sourceWeb of Sciencept_BR
dc.identifier.issn1477-0520pt_BR
dc.identifier.wosidWOS:000325119600015pt_BR
dc.identifier.doi10.1039/c3ob41207ept_BR
dc.description.sponsorshipFundação de Amparo à Pesquisa do Estado de Minas Gerais (FAPEMIG)pt_BR
dc.description.sponsorshipFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)pt_BR
dc.description.sponsorshipConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)pt_BR
dc.description.sponsorship1Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)pt_BR
dc.description.sponsorship1Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)pt_BR
dc.date.available2014-07-30T19:00:05Z
dc.date.available2015-11-26T17:50:02Z-
dc.date.accessioned2014-07-30T19:00:05Z
dc.date.accessioned2015-11-26T17:50:02Z-
dc.description.provenanceMade available in DSpace on 2014-07-30T19:00:05Z (GMT). No. of bitstreams: 0 Previous issue date: 2013en
dc.description.provenanceMade available in DSpace on 2015-11-26T17:50:02Z (GMT). No. of bitstreams: 0 Previous issue date: 2013en
dc.identifier.urihttp://www.repositorio.unicamp.br/jspui/handle/REPOSIP/72270
dc.identifier.urihttp://repositorio.unicamp.br/jspui/handle/REPOSIP/72270-
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