Infrared and theoretical calculations in 2-halocycloheptanones conformational analysis

dc.creatorRozada, TC
dc.creatorGauze, GF
dc.creatorFavaro, DC
dc.creatorRittner, R
dc.creatorBasso, EA
dc.date2012
dc.dateAUG
dc.date2014-08-01T18:32:46Z
dc.date2015-11-26T17:03:13Z
dc.date2014-08-01T18:32:46Z
dc.date2015-11-26T17:03:13Z
dc.date.accessioned2018-03-28T23:51:18Z
dc.date.available2018-03-28T23:51:18Z
dc.identifierSpectrochimica Acta Part A-molecular And Biomolecular Spectroscopy. Pergamon-elsevier Science Ltd, v. 94, n. 277, n. 287, 2012.
dc.identifier1386-1425
dc.identifierWOS:000305853700038
dc.identifier10.1016/j.saa.2012.03.027
dc.identifierhttp://www.repositorio.unicamp.br/jspui/handle/REPOSIP/80517
dc.identifierhttp://repositorio.unicamp.br/jspui/handle/REPOSIP/80517
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/1279027
dc.descriptionConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
dc.descriptionFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.descriptionCoordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)
dc.description2-Halocycloheptanones (Halo = F, Cl, Br and I) were synthesized and their conformational analysis was performed through infrared spectroscopy data. The corresponding conformers geometries and energies were obtained by theoretical calculations at B3LYP/aug-cc-pVDZ level of theory in the isolated state and in solution. It was observed, by both approaches, that the conformational preferences were very sensitive to the solvent polarity, since its increase led to an increase in the population of the more polar conformer. An analysis of these conformational equilibria showed they suffer also the influence of stereoelectronic effects, like hyperconjugation and steric effects. These results were interpreted using natural bond orbital (NBO) analysis, which indicated that the electronic delocalization to the orbital pi*c=o is directly involved in the stability increase of conformers I and II. The relative effect of the period of the halogen can also be noted, with changes in the conformational preferences and in the energies involved in the interactions of NBO. (C) 2012 Elsevier B.V. All rights reserved.
dc.description94
dc.description277
dc.description287
dc.descriptionConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
dc.descriptionFundacao Araucaria [18070]
dc.descriptionFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.descriptionCoordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)
dc.descriptionConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
dc.descriptionFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.descriptionCoordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)
dc.descriptionFundacao Araucaria [18070]
dc.descriptionFAPESP [05/59649-0]
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.subject2-Halocycloheptanones
dc.subjectConformation analyses
dc.subjectInfrared
dc.subjectTheoretical calculations
dc.subjectNBO
dc.subjectMolecular Calculations
dc.subjectOrbital Interactions
dc.subjectN-bromosuccinimide
dc.subjectCarbonyl-compounds
dc.subjectCycloheptanone
dc.subjectKetones
dc.subject2-halocyclohexanones
dc.subjectPreferences
dc.titleInfrared and theoretical calculations in 2-halocycloheptanones conformational analysis
dc.typeArtículos de revistas


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