ELECTRONIC INTERACTIONS IMPLIED BY THE NONADDITIVITY OF C-13 SUBSTITUENT PARAMETERS IN 2-SUBSTITUTED CYCLOHEXANONES

dc.creatorBASSO, EA
dc.creatorKAISER, C
dc.creatorRITTNER, R
dc.creatorLAMBERT, JB
dc.date1994
dc.dateAPR
dc.date2014-12-16T11:34:33Z
dc.date2015-11-26T18:01:44Z
dc.date2014-12-16T11:34:33Z
dc.date2015-11-26T18:01:44Z
dc.date.accessioned2018-03-29T00:43:22Z
dc.date.available2018-03-29T00:43:22Z
dc.identifierMagnetic Resonance In Chemistry. John Wiley & Sons Ltd, v. 32, n. 4, n. 205, n. 209, 1994.
dc.identifier0749-1581
dc.identifierWOS:A1994NG23700002
dc.identifier10.1002/mrc.1260320403
dc.identifierhttp://www.repositorio.unicamp.br/jspui/handle/REPOSIP/64530
dc.identifierhttp://www.repositorio.unicamp.br/handle/REPOSIP/64530
dc.identifierhttp://repositorio.unicamp.br/jspui/handle/REPOSIP/64530
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/1292060
dc.descriptionThe carbon-13 chemical shifts were assigned for all ring positions in cyclohexanone and 4-tert-butylcyclohexanone with H, F, Cl, Br, I, MeO, MeS, MeSe, Me(2)N, Me or tert-butyl in the 2-position. The substituent-induced shifts were calculated by difference from unsubstituted cyclohexanone or 4-tert-butylcyclohexanone. Both stereoisomers (cis and trans) were available for the 4-tert-butylcyclohexanones in all but one case. Comparison of the substituent-induced shifts for the cis (equatorial 2-substituent) and trans (axial 2-substituent) isomers provides stereochemical insight into the interactions between the 2-substituent and the carbonyl group that bring about non-additivity of the substituent effects. In the 2-equatorial isomer, the dipole-dipole interaction between the functional groups causes non-additivities for the C-2 carbon that depend largely on the electronegativity of the 2-substituent. In the 2-axial isomer, hyperconjugation or other orbital interactions between the groups cause non-additivities for the C-2 carbon that depend largely on the polarizability in addition to the electronegativity of the 2-substituent.
dc.description32
dc.description4
dc.description205
dc.description209
dc.languageen
dc.publisherJohn Wiley & Sons Ltd
dc.publisherW Sussex
dc.publisherInglaterra
dc.relationMagnetic Resonance In Chemistry
dc.relationMagn. Reson. Chem.
dc.rightsfechado
dc.rightshttp://olabout.wiley.com/WileyCDA/Section/id-406071.html
dc.sourceWeb of Science
dc.subjectNMR
dc.subjectC-13 NMR
dc.subjectO-17 NMR
dc.subjectCYCLOHEXANONES
dc.subjectORBITAL INTERACTIONS
dc.subjectPOLAR EFFECTS
dc.subjectSUBSTITUENT-INDUCED SHIFTS
dc.subjectC-13 Nmr
dc.titleELECTRONIC INTERACTIONS IMPLIED BY THE NONADDITIVITY OF C-13 SUBSTITUENT PARAMETERS IN 2-SUBSTITUTED CYCLOHEXANONES
dc.typeArtículos de revistas


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