Facile synthesis and characterization of symmetric N-[(Phenylcarbonyl) carbamothioyl]benzamide thiourea : experimental and theoretical investigations.
Autor(a) principal: | |
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Data de Publicação: | 2018 |
Outros Autores: | , , , , , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Institucional da UFOP |
Texto Completo: | http://www.repositorio.ufop.br/handle/123456789/11228 http://dx.doi.org/10.21577/0103-5053.20180129 |
Resumo: | 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. |
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Silveira, Rafael Gomes daCatão, Anderson José LopesCunha, Beatriz Nogueira daAlmeida, FernandoDiniz, Luan FarinelliClavijo, Juan Carlos TenorioEllena, Javier AlcidesKuznetsov, Aleksey EvgenyevichBatista, Alzir AzevedoAlcântara, Edésio2019-05-08T15:59:05Z2019-05-08T15:59:05Z2018SILVEIRA, 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. 2019.1678-4790http://www.repositorio.ufop.br/handle/123456789/11228http://dx.doi.org/10.21577/0103-5053.20180129A 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.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.info:eu-repo/semantics/openAccessThioureas derivativeIntramolecular hydrogen bondFacile synthesis and characterization of symmetric N-[(Phenylcarbonyl) carbamothioyl]benzamide thiourea : experimental and theoretical investigations.info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleengreponame:Repositório Institucional da UFOPinstname:Universidade Federal de Ouro Preto (UFOP)instacron:UFOPLICENSElicense.txtlicense.txttext/plain; charset=utf-8924http://www.repositorio.ufop.br/bitstream/123456789/11228/2/license.txt62604f8d955274beb56c80ce1ee5dcaeMD52ORIGINALARTIGO_FacileSynthesisCharacterization.pdfARTIGO_FacileSynthesisCharacterization.pdfapplication/pdf4033068http://www.repositorio.ufop.br/bitstream/123456789/11228/1/ARTIGO_FacileSynthesisCharacterization.pdf7a8df9695dc9548dd453e4de79775cceMD51123456789/112282019-05-08 11:59:05.526oai:localhost: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ório InstitucionalPUBhttp://www.repositorio.ufop.br/oai/requestrepositorio@ufop.edu.bropendoar:32332019-05-08T15:59:05Repositório Institucional da UFOP - Universidade Federal de Ouro Preto (UFOP)false |
dc.title.pt_BR.fl_str_mv |
Facile synthesis and characterization of symmetric N-[(Phenylcarbonyl) carbamothioyl]benzamide thiourea : experimental and theoretical investigations. |
title |
Facile synthesis and characterization of symmetric N-[(Phenylcarbonyl) carbamothioyl]benzamide thiourea : experimental and theoretical investigations. |
spellingShingle |
Facile synthesis and characterization of symmetric N-[(Phenylcarbonyl) carbamothioyl]benzamide thiourea : experimental and theoretical investigations. Silveira, Rafael Gomes da Thioureas derivative Intramolecular hydrogen bond |
title_short |
Facile synthesis and characterization of symmetric N-[(Phenylcarbonyl) carbamothioyl]benzamide thiourea : experimental and theoretical investigations. |
title_full |
Facile synthesis and characterization of symmetric N-[(Phenylcarbonyl) carbamothioyl]benzamide thiourea : experimental and theoretical investigations. |
title_fullStr |
Facile synthesis and characterization of symmetric N-[(Phenylcarbonyl) carbamothioyl]benzamide thiourea : experimental and theoretical investigations. |
title_full_unstemmed |
Facile synthesis and characterization of symmetric N-[(Phenylcarbonyl) carbamothioyl]benzamide thiourea : experimental and theoretical investigations. |
title_sort |
Facile synthesis and characterization of symmetric N-[(Phenylcarbonyl) carbamothioyl]benzamide thiourea : experimental and theoretical investigations. |
author |
Silveira, Rafael Gomes da |
author_facet |
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 |
author_role |
author |
author2 |
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 |
author2_role |
author author author author author author author author author |
dc.contributor.author.fl_str_mv |
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 |
dc.subject.por.fl_str_mv |
Thioureas derivative Intramolecular hydrogen bond |
topic |
Thioureas derivative Intramolecular hydrogen bond |
description |
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. |
publishDate |
2018 |
dc.date.issued.fl_str_mv |
2018 |
dc.date.accessioned.fl_str_mv |
2019-05-08T15:59:05Z |
dc.date.available.fl_str_mv |
2019-05-08T15:59:05Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
format |
article |
status_str |
publishedVersion |
dc.identifier.citation.fl_str_mv |
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. |
dc.identifier.uri.fl_str_mv |
http://www.repositorio.ufop.br/handle/123456789/11228 |
dc.identifier.issn.none.fl_str_mv |
1678-4790 |
dc.identifier.doi.pt_BR.fl_str_mv |
http://dx.doi.org/10.21577/0103-5053.20180129 |
identifier_str_mv |
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. 1678-4790 |
url |
http://www.repositorio.ufop.br/handle/123456789/11228 http://dx.doi.org/10.21577/0103-5053.20180129 |
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eng |
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