Synthesis, structural and spectroscopic studies of 1-(2-FUROYL)-3- phenylthiourea: a theoretical and experimental approach

Autores
Estévez Hernández, Osvaldo; Salomón, Fernando Federico; Duque, Julio; Rodríguez Hernández, Joelis; Gil, Diego Mauricio
Año de publicación
2016
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The thiourea derivative 1-(2-Furoyl)-3-phenylthiourea (FPT) was synthesized and characterized by using spectroscopic (IR, Raman, UV–VIS, 1H and 13C NMR) and structural methods (powder X-ray diffraction data). The experimental measurements were complemented with quantum chemical calculations. FPT crystallizes in the monoclinic crystal system, space group P21/c, with cell parameters a = 4.7679(5) Å, b = 20.9704(2) Å, c = 12.5109(5) Å and β = 109.811(10)°, V = 1176.87(3) Å3. In the crystal structure, the thiourea group makes dihedral angle of 43.8(5)° with the furoyl group, whereas the benzene ring is inclined by 24.3(4)°. The anti-syn geometry of the thiourea unit is stabilized by intramolecular N–H…O hydrogen bond between the H atom of the syn thioamide and the carbonyl O atom. In the crystal structure, molecules of FPT are packed through N–H···S, C–H···O and C–H···C hydrogen bonds, and a π–π interaction with offset arrangement. Hirshfeld surface analysis was performed in order to evaluate and quantify intermolecular interactions. The Hirshfeld surface analysis indicated that the H···H interactions comprise the majority of interactions. Shape index and curvedness clearly indicate π–π interactions in the compound FPT.
Fil: Estévez Hernández, Osvaldo. Universidad de La Habana; Cuba. Centro de Investigación en Ciencia Aplicada y Tecnología de Avanzada; México
Fil: Salomón, Fernando Federico. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia; Argentina
Fil: Duque, Julio. Universidad de La Habana; Cuba. Centro de Investigación en Ciencia Aplicada y Tecnología de Avanzada; México
Fil: Rodríguez Hernández, Joelis. Centro de Investigación en Química Aplicada. Departamento de Materiales Avanzados; México
Fil: Gil, Diego Mauricio. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia; Argentina
Materia
CRYSTAL STRUCTURE
FUROYLTHIOUREAS
QUANTUM CHEMICAL CALCULATIONS
SIMULATED ANNEALING
X-RAY POWDER DIFFRACTION
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/131921
Acceder
id CONICETDig_8bec61f20a6d9da62444ca8dd21ef3e8
oai_identifier_str oai:ri.conicet.gov.ar:11336/131921
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis, structural and spectroscopic studies of 1-(2-FUROYL)-3- phenylthiourea: a theoretical and experimental approachEstévez Hernández, OsvaldoSalomón, Fernando FedericoDuque, JulioRodríguez Hernández, JoelisGil, Diego MauricioCRYSTAL STRUCTUREFUROYLTHIOUREASQUANTUM CHEMICAL CALCULATIONSSIMULATED ANNEALINGX-RAY POWDER DIFFRACTIONhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The thiourea derivative 1-(2-Furoyl)-3-phenylthiourea (FPT) was synthesized and characterized by using spectroscopic (IR, Raman, UV–VIS, 1H and 13C NMR) and structural methods (powder X-ray diffraction data). The experimental measurements were complemented with quantum chemical calculations. FPT crystallizes in the monoclinic crystal system, space group P21/c, with cell parameters a = 4.7679(5) Å, b = 20.9704(2) Å, c = 12.5109(5) Å and β = 109.811(10)°, V = 1176.87(3) Å3. In the crystal structure, the thiourea group makes dihedral angle of 43.8(5)° with the furoyl group, whereas the benzene ring is inclined by 24.3(4)°. The anti-syn geometry of the thiourea unit is stabilized by intramolecular N–H…O hydrogen bond between the H atom of the syn thioamide and the carbonyl O atom. In the crystal structure, molecules of FPT are packed through N–H···S, C–H···O and C–H···C hydrogen bonds, and a π–π interaction with offset arrangement. Hirshfeld surface analysis was performed in order to evaluate and quantify intermolecular interactions. The Hirshfeld surface analysis indicated that the H···H interactions comprise the majority of interactions. Shape index and curvedness clearly indicate π–π interactions in the compound FPT.Fil: Estévez Hernández, Osvaldo. Universidad de La Habana; Cuba. Centro de Investigación en Ciencia Aplicada y Tecnología de Avanzada; MéxicoFil: Salomón, Fernando Federico. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia; ArgentinaFil: Duque, Julio. Universidad de La Habana; Cuba. Centro de Investigación en Ciencia Aplicada y Tecnología de Avanzada; MéxicoFil: Rodríguez Hernández, Joelis. Centro de Investigación en Química Aplicada. Departamento de Materiales Avanzados; MéxicoFil: Gil, Diego Mauricio. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia; ArgentinaTaylor & Francis Ltd2016-09-03info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/131921Estévez Hernández, Osvaldo; Salomón, Fernando Federico; Duque, Julio; Rodríguez Hernández, Joelis; Gil, Diego Mauricio; Synthesis, structural and spectroscopic studies of 1-(2-FUROYL)-3- phenylthiourea: a theoretical and experimental approach; Taylor & Francis Ltd; Journal Of Sulfur Chemistry; 37; 5; 3-9-2016; 555-5791741-59931741-6000CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1080/17415993.2016.1209755info:eu-repo/semantics/altIdentifier/url/https://www.tandfonline.com/doi/full/10.1080/17415993.2016.1209755info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-11-26T08:53:27Zoai:ri.conicet.gov.ar:11336/131921instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-11-26 08:53:27.973CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis, structural and spectroscopic studies of 1-(2-FUROYL)-3- phenylthiourea: a theoretical and experimental approach
title Synthesis, structural and spectroscopic studies of 1-(2-FUROYL)-3- phenylthiourea: a theoretical and experimental approach
spellingShingle Synthesis, structural and spectroscopic studies of 1-(2-FUROYL)-3- phenylthiourea: a theoretical and experimental approach
Estévez Hernández, Osvaldo
CRYSTAL STRUCTURE
FUROYLTHIOUREAS
QUANTUM CHEMICAL CALCULATIONS
SIMULATED ANNEALING
X-RAY POWDER DIFFRACTION
title_short Synthesis, structural and spectroscopic studies of 1-(2-FUROYL)-3- phenylthiourea: a theoretical and experimental approach
title_full Synthesis, structural and spectroscopic studies of 1-(2-FUROYL)-3- phenylthiourea: a theoretical and experimental approach
title_fullStr Synthesis, structural and spectroscopic studies of 1-(2-FUROYL)-3- phenylthiourea: a theoretical and experimental approach
title_full_unstemmed Synthesis, structural and spectroscopic studies of 1-(2-FUROYL)-3- phenylthiourea: a theoretical and experimental approach
title_sort Synthesis, structural and spectroscopic studies of 1-(2-FUROYL)-3- phenylthiourea: a theoretical and experimental approach
dc.creator.none.fl_str_mv Estévez Hernández, Osvaldo
Salomón, Fernando Federico
Duque, Julio
Rodríguez Hernández, Joelis
Gil, Diego Mauricio
author Estévez Hernández, Osvaldo
author_facet Estévez Hernández, Osvaldo
Salomón, Fernando Federico
Duque, Julio
Rodríguez Hernández, Joelis
Gil, Diego Mauricio
author_role author
author2 Salomón, Fernando Federico
Duque, Julio
Rodríguez Hernández, Joelis
Gil, Diego Mauricio
author2_role author
author
author
author
dc.subject.none.fl_str_mv CRYSTAL STRUCTURE
FUROYLTHIOUREAS
QUANTUM CHEMICAL CALCULATIONS
SIMULATED ANNEALING
X-RAY POWDER DIFFRACTION
topic CRYSTAL STRUCTURE
FUROYLTHIOUREAS
QUANTUM CHEMICAL CALCULATIONS
SIMULATED ANNEALING
X-RAY POWDER DIFFRACTION
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The thiourea derivative 1-(2-Furoyl)-3-phenylthiourea (FPT) was synthesized and characterized by using spectroscopic (IR, Raman, UV–VIS, 1H and 13C NMR) and structural methods (powder X-ray diffraction data). The experimental measurements were complemented with quantum chemical calculations. FPT crystallizes in the monoclinic crystal system, space group P21/c, with cell parameters a = 4.7679(5) Å, b = 20.9704(2) Å, c = 12.5109(5) Å and β = 109.811(10)°, V = 1176.87(3) Å3. In the crystal structure, the thiourea group makes dihedral angle of 43.8(5)° with the furoyl group, whereas the benzene ring is inclined by 24.3(4)°. The anti-syn geometry of the thiourea unit is stabilized by intramolecular N–H…O hydrogen bond between the H atom of the syn thioamide and the carbonyl O atom. In the crystal structure, molecules of FPT are packed through N–H···S, C–H···O and C–H···C hydrogen bonds, and a π–π interaction with offset arrangement. Hirshfeld surface analysis was performed in order to evaluate and quantify intermolecular interactions. The Hirshfeld surface analysis indicated that the H···H interactions comprise the majority of interactions. Shape index and curvedness clearly indicate π–π interactions in the compound FPT.
Fil: Estévez Hernández, Osvaldo. Universidad de La Habana; Cuba. Centro de Investigación en Ciencia Aplicada y Tecnología de Avanzada; México
Fil: Salomón, Fernando Federico. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia; Argentina
Fil: Duque, Julio. Universidad de La Habana; Cuba. Centro de Investigación en Ciencia Aplicada y Tecnología de Avanzada; México
Fil: Rodríguez Hernández, Joelis. Centro de Investigación en Química Aplicada. Departamento de Materiales Avanzados; México
Fil: Gil, Diego Mauricio. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia; Argentina
description The thiourea derivative 1-(2-Furoyl)-3-phenylthiourea (FPT) was synthesized and characterized by using spectroscopic (IR, Raman, UV–VIS, 1H and 13C NMR) and structural methods (powder X-ray diffraction data). The experimental measurements were complemented with quantum chemical calculations. FPT crystallizes in the monoclinic crystal system, space group P21/c, with cell parameters a = 4.7679(5) Å, b = 20.9704(2) Å, c = 12.5109(5) Å and β = 109.811(10)°, V = 1176.87(3) Å3. In the crystal structure, the thiourea group makes dihedral angle of 43.8(5)° with the furoyl group, whereas the benzene ring is inclined by 24.3(4)°. The anti-syn geometry of the thiourea unit is stabilized by intramolecular N–H…O hydrogen bond between the H atom of the syn thioamide and the carbonyl O atom. In the crystal structure, molecules of FPT are packed through N–H···S, C–H···O and C–H···C hydrogen bonds, and a π–π interaction with offset arrangement. Hirshfeld surface analysis was performed in order to evaluate and quantify intermolecular interactions. The Hirshfeld surface analysis indicated that the H···H interactions comprise the majority of interactions. Shape index and curvedness clearly indicate π–π interactions in the compound FPT.
publishDate 2016
dc.date.none.fl_str_mv 2016-09-03
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/131921
Estévez Hernández, Osvaldo; Salomón, Fernando Federico; Duque, Julio; Rodríguez Hernández, Joelis; Gil, Diego Mauricio; Synthesis, structural and spectroscopic studies of 1-(2-FUROYL)-3- phenylthiourea: a theoretical and experimental approach; Taylor & Francis Ltd; Journal Of Sulfur Chemistry; 37; 5; 3-9-2016; 555-579
1741-5993
1741-6000
CONICET Digital
CONICET
url http://hdl.handle.net/11336/131921
identifier_str_mv Estévez Hernández, Osvaldo; Salomón, Fernando Federico; Duque, Julio; Rodríguez Hernández, Joelis; Gil, Diego Mauricio; Synthesis, structural and spectroscopic studies of 1-(2-FUROYL)-3- phenylthiourea: a theoretical and experimental approach; Taylor & Francis Ltd; Journal Of Sulfur Chemistry; 37; 5; 3-9-2016; 555-579
1741-5993
1741-6000
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1080/17415993.2016.1209755
info:eu-repo/semantics/altIdentifier/url/https://www.tandfonline.com/doi/full/10.1080/17415993.2016.1209755
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Taylor & Francis Ltd
publisher.none.fl_str_mv Taylor & Francis Ltd
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
_version_ 1849872982927736832
score 13.011256

Publicaciones similares