Please use this identifier to cite or link to this item: http://www.repositorio.ufop.br/handle/123456789/11228
Title: Facile synthesis and characterization of symmetric N-[(Phenylcarbonyl) carbamothioyl]benzamide thiourea : experimental and theoretical investigations.
Authors: Silveira, Rafael Gomes da
Catão, Anderson José Lopes
Cunha, Beatriz Nogueira da
Almeida, Fernando
Diniz, Luan Farinelli
Clavijo, Juan Carlos Tenorio
Ellena, Javier Alcides
Kuznetsov, Aleksey Evgenyevich
Batista, Alzir Azevedo
Alcântara, Edésio
Keywords: Thioureas derivative
Intramolecular hydrogen bond
Issue Date: 2018
Citation: SILVEIRA, R. G. da et al. Facile synthesis and characterization of symmetric N-[(Phenylcarbonyl) carbamothioyl]benzamide thiourea : experimental and theoretical investigations. Journal of the Brazilian Chemical Society, São Paulo, v. 29, n. 12, p. 2502-2513, 2018. Disponível em: <http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532018001202502>. Acesso em: 7 mar. 2019.
Abstract: A thiourea derivative, N-[(phenylcarbonyl)carbamothioyl]benzamide, was synthesized and characterized by elemental analysis, thermal analysis, spectroscopic methods (Fourier transform infrared (FTIR), UV-Vis, Raman, matrix-assisted laser desorption-ionization time-of-flight mass spectrometry (MALDI-TOF), tandem mass spectrometry (MS/MS) and nuclear magnetic resonance (NMR)) and quantum-chemical calculations. The synthetic route was simple and efficient, conducted just by one-step and no purification step was needed. The compound crystallizes in a non-centrosymmetric orthorhombic crystal system with a P21 21 21 space group, with a= 5.06220(10) Å, b= 11.8623(3) Å, c= 21.9682(8) Å. The molecular conformation of the solid is stabilized by the N-H···O intramolecular hydrogen bond, which was present in the X-ray structure and was also found in the optimized geometry. The theoretical analysis showed that this strong interaction remains even when molecules are solvated, i.e., the rotation barrier and the hydrogen bond strength are greater than the solvent stabilization energy. In addition to this hydrogen bond effect, the relative position of phenyl groups has a certain influence on the chemical behavior of this thiourea and probably for other phenylthioureas.
URI: http://www.repositorio.ufop.br/handle/123456789/11228
metadata.dc.identifier.doi: http://dx.doi.org/10.21577/0103-5053.20180129
ISSN: 1678-4790
metadata.dc.rights.license: Todo o conteúdo do periódico Journal of the Brazilian Chemical Society, exceto onde identificado, está sob uma licença Creative Commons 4.0 que permite copiar, distribuir e transmitir o trabalho em qualquer suporte ou formato desde que sejam citados o autor e o licenciante. Fonte: Journal of the Brazilian Chemical Society <http://www.scielo.br/scielo.php?script=sci_serial&pid=0103-5053&lng=en&nrm=iso>. Acesso em: 02 jan. 2017.
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