Conformer dipole moment and syn-1,3-diaxial steric effect on the conformational equilibrium of the cis isomer of some 1,3-disubstituted cyclohexanes

dc.creatorde Oliveira, PR
dc.creatorRittner, R
dc.date2005
dc.dateMAY 31
dc.date2014-11-20T00:02:00Z
dc.date2015-11-26T18:07:44Z
dc.date2014-11-20T00:02:00Z
dc.date2015-11-26T18:07:44Z
dc.date.accessioned2018-03-29T00:49:53Z
dc.date.available2018-03-29T00:49:53Z
dc.identifierJournal Of Molecular Structure. Elsevier Science Bv, v. 743, n. 41699, n. 69, n. 72, 2005.
dc.identifier0022-2860
dc.identifierWOS:000229412200008
dc.identifier10.1016/j.molstruc.2005.02.028
dc.identifierhttp://www.repositorio.unicamp.br/jspui/handle/REPOSIP/56541
dc.identifierhttp://www.repositorio.unicamp.br/handle/REPOSIP/56541
dc.identifierhttp://repositorio.unicamp.br/jspui/handle/REPOSIP/56541
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/1293659
dc.descriptionThe theoretical values of the dipole moment for the diaxial (ax-ax) conformer are larger than for the eq-eq conformer of some cis-3-halocyclohexanols (halo=Cl, Br and I) and c, S-3-halo-1-methoxycyclohexanes (halo=F, Cl, Brand 1). The experimental (3)J(HH) Coupling constants are rather large (> 10 Hz) indicating that the diequatorial (eq-eq) conformer is predominant for all compounds in the solvents studied. Dipole moments and NMR data lead to the conclusion that the conformational. equilibra of these 1,3-derivatives are not controlled by the solvent polarity, as is observed for the 1,2-disubstituted cyclohexanes, but are dictated by the syn-1,3-diaxial steric effect, which predominates over stabilization of the ax-ax conformer by an intramolecular hydrogen bond (IAHB). © 2005 Elsevier B.V. All rights reserved.
dc.description743
dc.description41699
dc.description69
dc.description72
dc.languageen
dc.publisherElsevier Science Bv
dc.publisherAmsterdam
dc.publisherHolanda
dc.relationJournal Of Molecular Structure
dc.relationJ. Mol. Struct.
dc.rightsfechado
dc.rightshttp://www.elsevier.com/about/open-access/open-access-policies/article-posting-policy
dc.sourceWeb of Science
dc.subjectconformational analysis
dc.subjecttheoretical calculations
dc.subjectsolvent effects
dc.subject1,3-disubstituted cyclohexanes
dc.subjectdipole moments
dc.subjectH-1 NMR coupling constants
dc.titleConformer dipole moment and syn-1,3-diaxial steric effect on the conformational equilibrium of the cis isomer of some 1,3-disubstituted cyclohexanes
dc.typeArtículos de revistas


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