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dc.creatorSilva, Thayná F. B.-
dc.creatorAndrade, Laize A. F.-
dc.creatorSilla, Josué M.-
dc.creatorDuarte, Claudimar J.-
dc.creatorRittner, Roberto-
dc.creatorFreitas, Matheus P.-
dc.date.accessioned2020-07-12T23:43:09Z-
dc.date.available2020-07-12T23:43:09Z-
dc.date.issued2014-07-25-
dc.identifier.citationSILVA, T. F. B. et al. Endocyclic oxygen in 3-fluorodihydro-2H-pyran-4(3H)-one that does not induce the gauche effect. The Journal of Physical Chemistry A, [S.l.], v. 118, n. 32, p. 6266-6271, July 2014. DOI: 10.1021/jp505573x.pt_BR
dc.identifier.urihttps://pubs.acs.org/doi/10.1021/jp505573xpt_BR
dc.identifier.urihttp://repositorio.ufla.br/jspui/handle/1/41847-
dc.description.abstract2-Fluorocyclohexanone undergoes chair inversion, giving rise to axial and equatorial conformers, with the equatorial form being highly preferred in solution, for example, 87% in chloroform and 93% in methylene chloride. Modifications in the conformational preferences can modify macroscopic properties of 2-fluoro ketones. The introduction of an endocyclic oxygen in 2-fluorocyclohexanone to give 3-fluorodihydro-2H-pyran-4(3H)-one would be expected to create a gauche effect in the axial conformer along with the O–C–C–F moiety, inducing an increase of its population. However, small changes were verified in the conformational populations both in the gas phase and solution because the carbonyl group plays an important role for the hyperconjugation in the equatorial conformer, despite experiencing strong dipolar repulsion with the fluorine atom. These data were obtained theoretically and by NMR spectroscopy, while the nature of the interactions governing these conformational shifts were investigated on the basis of natural bond orbital analysis.pt_BR
dc.languageen_USpt_BR
dc.publisherAmerican Chemical Society (ACS)pt_BR
dc.rightsrestrictAccesspt_BR
dc.sourceJournal of Physical Chemistry Apt_BR
dc.subjectFluorinept_BR
dc.subjectOxygenpt_BR
dc.subjectConformationpt_BR
dc.subjectMolecular structurept_BR
dc.subjectGasespt_BR
dc.titleEndocyclic oxygen in 3-fluorodihydro-2H-pyran-4(3H)-one that does not induce the gauche effectpt_BR
dc.typeArtigopt_BR
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