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dc.contributor.CRUESPUNIVERSIDADE ESTADUAL DE CAMPINASpt_BR
dc.contributor.authorunicampRittner Neto, Roberto-
dc.typeArtigopt_BR
dc.titleSpectroscopic and theoretical studies of some N-methoxy-N-methyl-2-[(4′-substituted) phenylsulfonyl]propanamidespt_BR
dc.contributor.authorOlivato, Paulo R.-
dc.contributor.authorDomingues, Nelson L. C.-
dc.contributor.authorReis, Adriana K. C. A.-
dc.contributor.authorVinhato, Elisângela-
dc.contributor.authorMondino, Mirta G.-
dc.contributor.authorZukerman-Schpector, Julio-
dc.contributor.authorRittner, Roberto-
dc.contributor.authorColle, Maurizio Dal-
dc.subjectAnálise conformacionalpt_BR
dc.subject.otherlanguageConformational analysispt_BR
dc.description.abstractThe analysis of the IR carbonyl band of the N-methoxy-N-methyl-2-[(4′-substituted)phenylsulfonyl]propanamides Y-PhSO2CH(Me)C(O)N(OMe)Me (Y = OMe 1, Me 2, H 3, Cl 4, NO2 5), supported by HF/6-31G(d,p) calculations of 3, indicated the existence of two gauche conformers (g1 and g2), the g1 conformer being the most stable and the least polar one (in gas phase and in solution). Both conformers are present in solution of the non polar solvent (CCl4) for 1–5 and in solution of the more polar solvents (CHCl3) for 1, 4, 5 and (CH2Cl2) for 5, while only the g1 conformer is present in solution of the most polar solvent (CH3CN) for 1–5. The g1 and g2 conformers correspond to the enantiomeric pairs of diastereomers (diast1 and diast2) whose relative configurations are [C(3)RNR]/[C(3)SNS] and [C(3)RNS]/[C(3)SNR], respectively. The computed carbonyl frequencies for g1 (diast1) and g2 (diast2) stereoisomers of 3 match well the experimental values. The NBO analysis, for 3 shows the important role of the orbital interactions in conformer stabilization and the overall balance of these interactions corroborates that the g1 conformer is more stable than the g2 one. The observed abnormal solvent effect on the relative intensities of the carbonyl doublet components is attributed to the molecular crowding in the g2 conformer which hinders its solvation in comparison to the g1 conformer (diast1). X-ray single crystal analysis performed for 3 shows the existence of two g2a and g1b conformers of diastereomers (diast2a and diast1b) whose absolute configurations are [C(3)RNS] and [C(3)RNR], respectively. The larger population and, thus, the larger stabilization of the g2a conformer over the g1b form in the crystals may be associated with a larger energy gain deriving from dipole moment coupling in the former conformer along with a series of CH…O electrostatic and hydrogen bond interactionspt_BR
dc.relation.ispartofJournal of molecular structurept_BR
dc.publisher.cityAmsterdampt_BR
dc.publisher.countryPaíses Baixospt_BR
dc.publisherElsevierpt_BR
dc.date.issued2009-
dc.date.monthofcirculationOct.pt_BR
dc.language.isoengpt_BR
dc.description.volume935pt_BR
dc.description.issuenumber1/3pt_BR
dc.description.firstpage60pt_BR
dc.description.lastpage68pt_BR
dc.rightsFechadopt_BR
dc.sourceWOSpt_BR
dc.identifier.issn0022-2860pt_BR
dc.identifier.eissn1872-8014pt_BR
dc.identifier.doi10.1016/j.molstruc.2009.06.038pt_BR
dc.identifier.urlhttps://www.sciencedirect.com/science/article/pii/S0022286009004190pt_BR
dc.description.sponsorshipCONSELHO NACIONAL DE DESENVOLVIMENTO CIENTÍFICO E TECNOLÓGICO - CNPQpt_BR
dc.description.sponsorshipFUNDAÇÃO DE AMPARO À PESQUISA DO ESTADO DE SÃO PAULO - FAPESPpt_BR
dc.description.sponsordocumentnumberSem informaçãopt_BR
dc.description.sponsordocumentnumberSem informaçãopt_BR
dc.date.available2020-09-02T18:20:26Z-
dc.date.accessioned2020-09-02T18:20:26Z-
dc.description.provenanceSubmitted by Thais de Brito Barroso (tbrito@unicamp.br) on 2020-09-02T18:20:26Z No. of bitstreams: 0. Added 1 bitstream(s) on 2021-01-04T15:12:24Z : No. of bitstreams: 1 000270603000010.pdf: 570844 bytes, checksum: 4c82a0442cb21ee0b95b72674daf9b71 (MD5)en
dc.description.provenanceMade available in DSpace on 2020-09-02T18:20:26Z (GMT). No. of bitstreams: 0 Previous issue date: 2009en
dc.identifier.urihttp://repositorio.unicamp.br/jspui/handle/REPOSIP/348576-
dc.contributor.departmentDepartamento de Química Orgânicapt_BR
dc.contributor.unidadeInstituto de Químicapt_BR
dc.subject.keywordInfrared spectroscopypt_BR
dc.subject.keywordTheoretical calculationspt_BR
dc.subject.keywordN-methoxy-N-methyl-2-[(40-substituted)phenylsulfonyl]propanamidespt_BR
dc.identifier.source000270603000010pt_BR
dc.creator.orcid0000-0002-4715-6139pt_BR
dc.type.formArtigopt_BR
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