C-13 NMR, infrared, solvation and theoretical investigation of the conformational isomerism in 1-haloacetones (X = Cl, Br and I)

dc.creatorDoi, TR
dc.creatorYoshinaga, F
dc.creatorTormena, CF
dc.creatorRittner, R
dc.creatorAbraham, RJ
dc.date2005
dc.dateJUL
dc.date2014-11-14T08:54:18Z
dc.date2015-11-26T17:14:10Z
dc.date2014-11-14T08:54:18Z
dc.date2015-11-26T17:14:10Z
dc.date.accessioned2018-03-29T00:02:30Z
dc.date.available2018-03-29T00:02:30Z
dc.identifierSpectrochimica Acta Part A-molecular And Biomolecular Spectroscopy. Pergamon-elsevier Science Ltd, v. 61, n. 9, n. 2221, n. 2230, 2005.
dc.identifier1386-1425
dc.identifierWOS:000229841100035
dc.identifier10.1016/j.saa.2004.08.021
dc.identifierhttp://www.repositorio.unicamp.br/jspui/handle/REPOSIP/63338
dc.identifierhttp://www.repositorio.unicamp.br/handle/REPOSIP/63338
dc.identifierhttp://repositorio.unicamp.br/jspui/handle/REPOSIP/63338
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/1281748
dc.descriptionThe solvent dependence of the C-13 NMR spectra of chloroacetone (CA), bromoacetone (BA) and iodoacetone (IA) are reported and the (3)J(CH) couplings analysed using ab initio calculations and solvation theory. In CA the energy difference (E-cis - E-gauche) between the cis (Cl-C-C=O 0 degrees) and gauche (Cl-C-C=O 155 degrees) conformers is 1.7 kcal mol(-1) in the vapour, decreasing to 0.8 kcat mol(-1) in CCl4 solution and to - 1.0 kcal mol(-1) in the pure liquid. The conformational equilibrium, in BA, is between the more polar cis (Br-C-C=O 0 degrees) and gauche (Br-C-C=O 132 degrees) conformations. The energy difference (E-cis - E-gauche) is 1.8 kcal mol(-1) in the vapour, decreasing to 0.9 kcal mol(-1) in CCl4 solution and to -0.4 kcal mol(-1) in the pure liquid. The energy difference (Ecis - Egauche), in IA, between the cis (Cl-C-C=O 0 degrees) and gauche (I-C-C=O 104 degrees) conformers is 1.1 kcal mol(-1) in the vapour phase, decreasing to 0.5 kcal mol(-1) in CCl4 solution and to -0.5 kcal mol(-1) in the pure liquid. The vapour state energy difference for BA [1.4 kcal mol(-1) at B3LYP/6-311++G(d,p)] and for IA [1.6 kcal mol(-1) at B3LYP/6-311++G(d,p)/LANL2DZ)] are in very good agreement with the above values. For CA the agreement is also satisfactory [1.4 kcal mol(-1) at B3LYP/6-311++G(d,p)]. (c) 2004 Elsevier B.V. All rights reserved.
dc.description61
dc.description9
dc.description2221
dc.description2230
dc.languageen
dc.publisherPergamon-elsevier Science Ltd
dc.publisherOxford
dc.publisherInglaterra
dc.relationSpectrochimica Acta Part A-molecular And Biomolecular Spectroscopy
dc.relationSpectroc. Acta Pt. A-Molec. Biomolec. Spectr.
dc.rightsfechado
dc.rightshttp://www.elsevier.com/about/open-access/open-access-policies/article-posting-policy
dc.sourceWeb of Science
dc.subjectconformational analysis
dc.subjectNMR spectroscopy
dc.subjecttheoretical calculations
dc.subjecthaloacetones
dc.subjectSpin Coupling-constants
dc.subjectRotational-isomerism
dc.subjectVibrational Assignment
dc.subjectElectronic Interaction
dc.subjectCarbonyl-compounds
dc.subjectInternal-rotation
dc.subjectRaman-spectra
dc.subjectBromoacetone
dc.subjectChloroacetone
dc.subjectAcetones
dc.titleC-13 NMR, infrared, solvation and theoretical investigation of the conformational isomerism in 1-haloacetones (X = Cl, Br and I)
dc.typeArtículos de revistas


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