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Title: Understanding the conformational changes and molecular structure of furoyl thioureas upon substitution.
Authors: Cairo, Raúl Ramos
Stevens, Ana María Plutín
Oliveira, Tamires Donizeth de
Batista, Alzir Azevedo
Castellano, Eduardo Ernesto
Duque, Julio
Soria, Delia B.
Fantoni, Adolfo C.
Correa, Rodrigo de Souza
Erbene, Mauricio F.
Keywords: Thiourea derivatives
Vibrational spectroscopy
Single crystal structure determination
Molecular conformation
Issue Date: 2017
Citation: CAIRO, R. 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: <>. Acesso em: 15 set. 2017.
Abstract: 1-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.
ISSN:  1386-1425
metadata.dc.rights.license: O periódico Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy concede permissão para depósito deste artigo no Repositório Institucional da UFOP. Número da licença: 4211371480250.
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