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dc.creatorMartins, Francisco A.-
dc.creatorFreitas, Matheus P.-
dc.date.accessioned2020-05-12T18:28:03Z-
dc.date.available2020-05-12T18:28:03Z-
dc.date.issued2019-10-09-
dc.identifier.citationMARTINS, F. A.; FREITAS, M. P. The Fluorine gauche effect and a comparison with Other halogens in 2‐Halofluoroethanes and 2‐Haloethanols. Chemistry Europe, [S.l.], v. 2019, n. 37, p. 6401-6406, 9 Oct. 2019.pt_BR
dc.identifier.urihttps://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.201901234pt_BR
dc.identifier.urihttp://repositorio.ufla.br/jspui/handle/1/40849-
dc.description.abstractWhile the gauche effect in 1,2‐difluoroethane is widely known as being due to hyperconjugative interactions between σCH electron‐donating orbitals and σ*CF electron‐accepting orbitals, the corresponding 1,2‐dichloro, 1,2‐dibromo, and 1,2‐diiodo derivatives are preferentially in the anti conformation. 2‐Halofluoroethanes (F‐CH2‐CH2‐X) combine a small halogen (fluorine) and a vicinal low‐lying energy antibonding orbital (σ*CX) that activates a stabilizing antiperiplanar σCH → σ*CX electron delocalization, which can induce the gauche effect. On the other hand, σCX orbitals are good electron donors to σ*CF, that would favor an “anti effect”, in addition to traditional interpretations based on steric and electrostatic repulsion. Therefore, a balance of steric, dipolar and hyperconjugative effects drive the conformational equilibrium of these compounds – hyperconjugation was found to explain the gauche effect in some cases, whilst Lewis‐type interactions determine the anti preference in others. The gauche effect takes place in a polar solvent, but not for 1‐fluoro‐2‐iodoethane. According to NMR three‐bond spin‐spin coupling constants, the gauche population increases when fluorine is replaced by a hydroxyl group (except for 2‐fluoroethanol relative to 1,2‐difluoroethane), but this is not primarily due to intramolecular hydrogen bond.pt_BR
dc.languageen_USpt_BR
dc.publisherWileypt_BR
dc.rightsrestrictAccesspt_BR
dc.sourceChemistry Europept_BR
dc.subjectDipolar interactionspt_BR
dc.subjectHyperconjugationpt_BR
dc.subjectSteric effectspt_BR
dc.subjectIntramolecular hydrogen bondspt_BR
dc.subjectInterações dipolarespt_BR
dc.subjectHiperconjugaçãopt_BR
dc.subjectEfeitos estéricospt_BR
dc.subjectLigações intramoleculares de hidrogêniopt_BR
dc.titleThe Fluorine gauche effect and a comparison with Other halogens in 2‐Halofluoroethanes and 2‐Haloethanolspt_BR
dc.typeArtigopt_BR
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