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: | Journal of the Brazilian Chemical Society (Online) |
Texto Completo: | http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532018001202502 |
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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Facile Synthesis and Characterization of Symmetric N-[(Phenylcarbonyl) carbamothioyl]benzamide Thiourea: Experimental and Theoretical Investigationsthioureas derivativesynthesisintramolecular hydrogen bondA 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.Sociedade Brasileira de Química2018-12-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532018001202502Journal of the Brazilian Chemical Society v.29 n.12 2018reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.21577/0103-5053.20180129info:eu-repo/semantics/openAccessSilveira,Rafael G.Catão,Anderson J. L.Cunha,Beatriz N.Almeida,FernandoCorrea,Rodrigo S.Diniz,Luan F.Tenório,Juan C.Ellena,JavierKuznetsov,Aleksey E.Batista,Alzir A.Alcântara,Edésioeng2018-11-26T00:00:00Zoai:scielo:S0103-50532018001202502Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2018-11-26T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false |
dc.title.none.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 G. thioureas derivative synthesis 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 G. |
author_facet |
Silveira,Rafael G. Catão,Anderson J. L. Cunha,Beatriz N. Almeida,Fernando Correa,Rodrigo S. Diniz,Luan F. Tenório,Juan C. Ellena,Javier Kuznetsov,Aleksey E. Batista,Alzir A. Alcântara,Edésio |
author_role |
author |
author2 |
Catão,Anderson J. L. Cunha,Beatriz N. Almeida,Fernando Correa,Rodrigo S. Diniz,Luan F. Tenório,Juan C. Ellena,Javier Kuznetsov,Aleksey E. Batista,Alzir A. Alcântara,Edésio |
author2_role |
author author author author author author author author author author |
dc.contributor.author.fl_str_mv |
Silveira,Rafael G. Catão,Anderson J. L. Cunha,Beatriz N. Almeida,Fernando Correa,Rodrigo S. Diniz,Luan F. Tenório,Juan C. Ellena,Javier Kuznetsov,Aleksey E. Batista,Alzir A. Alcântara,Edésio |
dc.subject.por.fl_str_mv |
thioureas derivative synthesis intramolecular hydrogen bond |
topic |
thioureas derivative synthesis 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.none.fl_str_mv |
2018-12-01 |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532018001202502 |
url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532018001202502 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
10.21577/0103-5053.20180129 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
text/html |
dc.publisher.none.fl_str_mv |
Sociedade Brasileira de Química |
publisher.none.fl_str_mv |
Sociedade Brasileira de Química |
dc.source.none.fl_str_mv |
Journal of the Brazilian Chemical Society v.29 n.12 2018 reponame:Journal of the Brazilian Chemical Society (Online) instname:Sociedade Brasileira de Química (SBQ) instacron:SBQ |
instname_str |
Sociedade Brasileira de Química (SBQ) |
instacron_str |
SBQ |
institution |
SBQ |
reponame_str |
Journal of the Brazilian Chemical Society (Online) |
collection |
Journal of the Brazilian Chemical Society (Online) |
repository.name.fl_str_mv |
Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ) |
repository.mail.fl_str_mv |
||office@jbcs.sbq.org.br |
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1750318181277237248 |