Understanding the conformational changes and molecular structure of furoyl thioureas upon substitution.

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dc.contributor.authorRamos Cairo, Raúl
dc.contributor.authorStevens, Ana María Plutín
dc.contributor.authorOliveira, Tamires Donizeth de
dc.contributor.authorBatista, Alzir Azevedo
dc.contributor.authorCastellano, Eduardo Ernesto
dc.contributor.authorDuque, Julio
dc.contributor.authorSoria, Delia B.
dc.contributor.authorFantoni, Adolfo C.
dc.contributor.authorCorrea, Rodrigo de Souza
dc.contributor.authorErbene, Mauricio F.
dc.date.accessioned2018-03-15T13:28:02Z
dc.date.available2018-03-15T13:28:02Z
dc.date.issued2017
dc.description.abstract1-Acyl thioureas [R1C(O)NHC(S)NR2R3] are shown to display conformational flexibility depending on the degree of substitution at the nitrogen atom. The conformational landscape and structural features for two closely related thioureas having R1=2-furoyl have been studied. The un-substituted 2-furoyl thiourea (I) and its dimethyl analogue, i.e. 1-(2-furoyl)-3,3-dimethyl thiourea (II), have been synthesized and fully characterized by spectroscopic (FT-IR, 1H and 13C NMR) and elemental analysis. According to single crystal X-ray diffraction analysis, compounds I and II crystallize in the monoclinic space group P21/c. In the compound I, the trans–cis geometry of the almost planar thiourea unit is stabilized by intramolecular N\\H⋯O_C hydrogen bond between the H atom of the cis thioamide and the carbonyl O atom. In compound II, however, the acyl thiourea group is non-planar, in good agreement with the potential energy curve computed at the B3LYP/6-31+G(d,p) level of approximation. Centrosymmetric dimers generated by intermolecular N\\H⋯S_C hydrogen bond forming R2 2 (8) motif are present in the crystals. Intermolecular interactions have been rationalized in terms of topological partitions of the electron distributions and Hirshfeld surface analysis, which showed the occurrence of S⋯H, O⋯H and H⋯H contacts that display an important role to crystal packing stabilization of both thiourea derivatives.pt_BR
dc.identifier.citationRAMOS CAIRO, R. et al. Understanding the conformational changes and molecular structure of furoyl thioureas upon substitution. Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy, v. 176, p. 8-17, abr. 2017. Disponível em: <http://www.sciencedirect.com/science/article/pii/S1386142516307715>. Acesso em: 15 set. 2017.pt_BR
dc.identifier.doihttps://doi.org/10.1016/j.saa.2016.12.038
dc.identifier.issn 1386-1425
dc.identifier.urihttp://www.repositorio.ufop.br/handle/123456789/9637
dc.language.isoen_USpt_BR
dc.rightsabertopt_BR
dc.rights.licenseO periódico Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy concede permissão para depósito deste artigo no Repositório Institucional da UFOP. Número da licença: 4211371480250.pt_BR
dc.subjectThiourea derivativespt_BR
dc.subjectVibrational spectroscopypt_BR
dc.subjectSingle crystal structure determinationpt_BR
dc.subjectMolecular conformationpt_BR
dc.titleUnderstanding the conformational changes and molecular structure of furoyl thioureas upon substitution.pt_BR
dc.typeArtigo publicado em periodicopt_BR
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