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dc.contributor.CRUESPUNIVERSIDADE ESTADUAL DE CAMPINASpt_BR
dc.contributor.authorunicampTormena, Cláudio Francisco-
dc.contributor.authorunicampRittner Neto, Roberto-
dc.typeArtigopt_BR
dc.titleConformational and electronic interaction studies of some p-substituted α-methylsulfonyl-α-diethoxyphosphorylacetophenonespt_BR
dc.contributor.authorReis, Adriana Karla C. A.-
dc.contributor.authorOlivato, Paulo R.-
dc.contributor.authorTormena, Cláudio F.-
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 α-methylsulfonyl-α-diethoxyphosphoryl p-substituted acetophenones p-Y-Ph-C(O)CH(SO2Me)[P(O)(OEt)2] (Y = OMe 1, H 2, F 3, Cl 4, Br 5 and NO2 6) supported by HF/6-31G(d,p) ab initio calculations of the α-methylsulfonyl-α-diethoxyphosphoryl acetophenone 2, indicated the existence of a single stable c1 conformer in gas phase and in solvents of increasing polarity, along with the presence of second less stable conformation in gas phase. The c1 conformer present the (SO2Me) group and the [P(O)(OEt2)] groups in a syn-clinal (gauche) geometry and is stabilised through of the Oδ−(CO)...Pδ+(PO), Oδ−[PO(OEt)]...Cδ+(CO), Oδ−(PO)…Cδ+(CO), Oδ−(CO)…Sδ+(SO2Me) and Oδ−(SO2)...Cδ+(CO) electronic interactions along with Hδ+(SO2Me)…. Oδ−(CO), Hδ+(CH2)[POEt]…. Oδ−(SO2Me), Hδ+(o-Ph)…. Oδ−(CO) and Hδ+(o′-Ph)…. Oδ−(PO) intramolecular hydrogen bonds. The almost constant negative carbonyl frequency shifts (Δν) for the title compounds 1–6 with respect to the parent acetophenones 7–14 corroborates the prevalence of the electronic interactions over the −Iσ inductive effect of the α-substituents for the title compounds and gives strong support for the existence of the crossed Oδ−(CO)…Sδ+(SO2Me) and Oδ−(SO2)...Cδ+(CO) (charge transfer and electrostatic); Oδ−(CO)...Pδ+(PO) and Oδ−[PO(OEt)]...Cδ+(CO), (electrostatic) interactionspt_BR
dc.relation.ispartofJournal of molecular structurept_BR
dc.publisher.cityAmsterdampt_BR
dc.publisher.countryPaíses Baixospt_BR
dc.publisherElsevierpt_BR
dc.date.issued2008-
dc.date.monthofcirculationDec.pt_BR
dc.language.isoengpt_BR
dc.description.volume892pt_BR
dc.description.issuenumber1/3pt_BR
dc.description.firstpage300pt_BR
dc.description.lastpage304pt_BR
dc.rightsFechadopt_BR
dc.sourceWOSpt_BR
dc.identifier.issn0022-2860pt_BR
dc.identifier.eissn1872-8014pt_BR
dc.identifier.doi10.1016/j.molstruc.2008.05.055pt_BR
dc.identifier.urlhttps://www.sciencedirect.com/science/article/pii/S0022286008004298pt_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.available2020-09-02T20:08:30Z-
dc.date.accessioned2020-09-02T20:08:30Z-
dc.description.provenanceSubmitted by Thais de Brito Barroso (tbrito@unicamp.br) on 2020-09-02T20:08:30Z No. of bitstreams: 0. Added 1 bitstream(s) on 2021-01-04T15:12:26Z : No. of bitstreams: 1 000261711400049.pdf: 351077 bytes, checksum: d2d4a5773bafba0952694f3c35f5ff7e (MD5)en
dc.description.provenanceMade available in DSpace on 2020-09-02T20:08:30Z (GMT). No. of bitstreams: 0 Previous issue date: 2008en
dc.identifier.urihttp://repositorio.unicamp.br/jspui/handle/REPOSIP/348590-
dc.contributor.departmentDepartamento de Química Orgânicapt_BR
dc.contributor.departmentDepartamento de Química Orgânicapt_BR
dc.contributor.unidadeInstituto de Químicapt_BR
dc.contributor.unidadeInstituto de Químicapt_BR
dc.subject.keywordInfrared spectroscopypt_BR
dc.subject.keywordTheoretical calculations p-substituteda-methylsulfonyl-a-diethoxyphosphorylacetophenonespt_BR
dc.identifier.source000261711400049pt_BR
dc.creator.orcid0000-0002-1508-0694pt_BR
dc.creator.orcid0000-0002-4715-6139pt_BR
dc.type.formArtigopt_BR
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