NMR spin-spin couplings involving nuclei in the neighborhood of a carbonyl group. 3JCH couplings in α-substituted acetamides

dc.creatorPedersoli, Susimaire
dc.creatorDos Santos, Francisco P.
dc.creatorRittner, Roberto
dc.creatorContreras, Ruben Horacio
dc.creatorTormena, Cláudio F.
dc.date.accessioned2018-10-09T18:42:12Z
dc.date.accessioned2018-11-06T11:24:15Z
dc.date.available2018-10-09T18:42:12Z
dc.date.available2018-11-06T11:24:15Z
dc.date.created2018-10-09T18:42:12Z
dc.date.issued2008-03
dc.identifierPedersoli, Susimaire; Dos Santos, Francisco P.; Rittner, Roberto; Contreras, Ruben Horacio; Tormena, Cláudio F.; NMR spin-spin couplings involving nuclei in the neighborhood of a carbonyl group. 3JCH couplings in α-substituted acetamides; John Wiley & Sons Ltd; Magnetic Resonance in Chemistry; 46; 3; 3-2008; 202-205
dc.identifier0749-1581
dc.identifierhttp://hdl.handle.net/11336/61994
dc.identifierCONICET Digital
dc.identifierCONICET
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/1850757
dc.description.abstractIn this work 3JCH spin-spin coupling constants (SSCCs) for the cis- and trans-conformers for α-X-acetamides (X = F, Cl, Br and CN) (1-4) were studied in detail since they were found to be notably different for both conformers. These differences are rationalized as originating in the changes of the strong negative hyperconjugative interactions that take place within the carbonyl group. Such changes are found to depend not only on conformation, but also on solvent. For the cis-conformers there is a close proximity between the X-substituent and the in-plane oxygen lone pair of pure p character, which affects notably their respective negative hyperconjugative interactions. Both the efficiency for transmitting the Fermi contact (FC) term through the coupling pathway of 3JCH SSCCs and its potential as a probe to study the stereochemical properties of the XH 2C group are discussed. Copyright © 2008 John Wiley & Sons, Ltd.
dc.languageeng
dc.publisherJohn Wiley & Sons Ltd
dc.relationinfo:eu-repo/semantics/altIdentifier/doi/https://dx.doi.org/10.1002/mrc.2158
dc.relationinfo:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/mrc.2158
dc.rightshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.rightsinfo:eu-repo/semantics/restrictedAccess
dc.subject3JCH COUPLINGS
dc.subjectFC TRANSMISSION
dc.subjectNEGATIVE HYPERCONJUGATIVE INTERACTIONS
dc.titleNMR spin-spin couplings involving nuclei in the neighborhood of a carbonyl group. 3JCH couplings in α-substituted acetamides
dc.typeArtículos de revistas
dc.typeArtículos de revistas
dc.typeArtículos de revistas


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