Understanding the conformational changes and molecular structure of furoyl thioureas upon substitution

Autores
Ramos Cairo, Raúl; Plutín Stevens, Ana María; Donizeth de Oliveira, Tamires; Batista, Alzir A.; Castellano, Eduardo E.; Duque, Julio; Soria, Delia Beatriz; Fantoni, Adolfo Carlos; Corrêa, Rodrigo S.; Erben, Mauricio Federico
Año de publicación
2017
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
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[sbnd]H ⋯ O[dbnd]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[sbnd]H ⋯ S[dbnd]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.
Fil: Ramos Cairo, Raúl. Universidad de La Habana; Cuba
Fil: Plutín Stevens, Ana María. Universidad de La Habana; Cuba
Fil: Donizeth de Oliveira, Tamires. Universidade Federal do São Carlos; Brasil
Fil: Batista, Alzir A.. Universidade Federal do São Carlos; Brasil
Fil: Castellano, Eduardo E.. Universidad de La Habana; Cuba
Fil: Duque, Julio. Universidad de La Habana; Cuba
Fil: Soria, Delia Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina
Fil: Fantoni, Adolfo Carlos. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Física La Plata. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Física La Plata; Argentina
Fil: Corrêa, Rodrigo S.. Universidade Federal de Ouro Preto; Brasil
Fil: Erben, Mauricio Federico. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina
Materia
Hirshfeld Surface Analysis
Molecular Conformation
Single Crystal Structure Determination
Thiourea Derivatives
Topological Study
Vibrational Spectroscopy
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:11336/65408
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/65408
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Understanding the conformational changes and molecular structure of furoyl thioureas upon substitutionRamos Cairo, RaúlPlutín Stevens, Ana MaríaDonizeth de Oliveira, TamiresBatista, Alzir A.Castellano, Eduardo E.Duque, JulioSoria, Delia BeatrizFantoni, Adolfo CarlosCorrêa, Rodrigo S.Erben, Mauricio FedericoHirshfeld Surface AnalysisMolecular ConformationSingle Crystal Structure DeterminationThiourea DerivativesTopological StudyVibrational Spectroscopyhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/11-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[sbnd]H ⋯ O[dbnd]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[sbnd]H ⋯ S[dbnd]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.Fil: Ramos Cairo, Raúl. Universidad de La Habana; CubaFil: Plutín Stevens, Ana María. Universidad de La Habana; CubaFil: Donizeth de Oliveira, Tamires. Universidade Federal do São Carlos; BrasilFil: Batista, Alzir A.. Universidade Federal do São Carlos; BrasilFil: Castellano, Eduardo E.. Universidad de La Habana; CubaFil: Duque, Julio. Universidad de La Habana; CubaFil: Soria, Delia Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; ArgentinaFil: Fantoni, Adolfo Carlos. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Física La Plata. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Física La Plata; ArgentinaFil: Corrêa, Rodrigo S.. Universidade Federal de Ouro Preto; BrasilFil: Erben, Mauricio Federico. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; ArgentinaPergamon-Elsevier Science Ltd2017-04info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/65408Ramos Cairo, Raúl; Plutín Stevens, Ana María; Donizeth de Oliveira, Tamires; Batista, Alzir A.; Castellano, Eduardo E.; et al.; Understanding the conformational changes and molecular structure of furoyl thioureas upon substitution; Pergamon-Elsevier Science Ltd; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; 176; 4-2017; 8-171386-1425CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.saa.2016.12.038info:eu-repo/semantics/altIdentifier/url/https://linkinghub.elsevier.com/retrieve/pii/S1386142516307715info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T14:39:36Zoai:ri.conicet.gov.ar:11336/65408instacron: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:34982025-10-15 14:39:37.072CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Understanding the conformational changes and molecular structure of furoyl thioureas upon substitution
title Understanding the conformational changes and molecular structure of furoyl thioureas upon substitution
spellingShingle Understanding the conformational changes and molecular structure of furoyl thioureas upon substitution
Ramos Cairo, Raúl
Hirshfeld Surface Analysis
Molecular Conformation
Single Crystal Structure Determination
Thiourea Derivatives
Topological Study
Vibrational Spectroscopy
title_short Understanding the conformational changes and molecular structure of furoyl thioureas upon substitution
title_full Understanding the conformational changes and molecular structure of furoyl thioureas upon substitution
title_fullStr Understanding the conformational changes and molecular structure of furoyl thioureas upon substitution
title_full_unstemmed Understanding the conformational changes and molecular structure of furoyl thioureas upon substitution
title_sort Understanding the conformational changes and molecular structure of furoyl thioureas upon substitution
dc.creator.none.fl_str_mv Ramos Cairo, Raúl
Plutín Stevens, Ana María
Donizeth de Oliveira, Tamires
Batista, Alzir A.
Castellano, Eduardo E.
Duque, Julio
Soria, Delia Beatriz
Fantoni, Adolfo Carlos
Corrêa, Rodrigo S.
Erben, Mauricio Federico
author Ramos Cairo, Raúl
author_facet Ramos Cairo, Raúl
Plutín Stevens, Ana María
Donizeth de Oliveira, Tamires
Batista, Alzir A.
Castellano, Eduardo E.
Duque, Julio
Soria, Delia Beatriz
Fantoni, Adolfo Carlos
Corrêa, Rodrigo S.
Erben, Mauricio Federico
author_role author
author2 Plutín Stevens, Ana María
Donizeth de Oliveira, Tamires
Batista, Alzir A.
Castellano, Eduardo E.
Duque, Julio
Soria, Delia Beatriz
Fantoni, Adolfo Carlos
Corrêa, Rodrigo S.
Erben, Mauricio Federico
author2_role author
author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv Hirshfeld Surface Analysis
Molecular Conformation
Single Crystal Structure Determination
Thiourea Derivatives
Topological Study
Vibrational Spectroscopy
topic Hirshfeld Surface Analysis
Molecular Conformation
Single Crystal Structure Determination
Thiourea Derivatives
Topological Study
Vibrational Spectroscopy
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv 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[sbnd]H ⋯ O[dbnd]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[sbnd]H ⋯ S[dbnd]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.
Fil: Ramos Cairo, Raúl. Universidad de La Habana; Cuba
Fil: Plutín Stevens, Ana María. Universidad de La Habana; Cuba
Fil: Donizeth de Oliveira, Tamires. Universidade Federal do São Carlos; Brasil
Fil: Batista, Alzir A.. Universidade Federal do São Carlos; Brasil
Fil: Castellano, Eduardo E.. Universidad de La Habana; Cuba
Fil: Duque, Julio. Universidad de La Habana; Cuba
Fil: Soria, Delia Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina
Fil: Fantoni, Adolfo Carlos. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Física La Plata. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Física La Plata; Argentina
Fil: Corrêa, Rodrigo S.. Universidade Federal de Ouro Preto; Brasil
Fil: Erben, Mauricio Federico. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina
description 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[sbnd]H ⋯ O[dbnd]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[sbnd]H ⋯ S[dbnd]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.
publishDate 2017
dc.date.none.fl_str_mv 2017-04
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/11336/65408
Ramos Cairo, Raúl; Plutín Stevens, Ana María; Donizeth de Oliveira, Tamires; Batista, Alzir A.; Castellano, Eduardo E.; et al.; Understanding the conformational changes and molecular structure of furoyl thioureas upon substitution; Pergamon-Elsevier Science Ltd; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; 176; 4-2017; 8-17
1386-1425
CONICET Digital
CONICET
url http://hdl.handle.net/11336/65408
identifier_str_mv Ramos Cairo, Raúl; Plutín Stevens, Ana María; Donizeth de Oliveira, Tamires; Batista, Alzir A.; Castellano, Eduardo E.; et al.; Understanding the conformational changes and molecular structure of furoyl thioureas upon substitution; Pergamon-Elsevier Science Ltd; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; 176; 4-2017; 8-17
1386-1425
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1016/j.saa.2016.12.038
info:eu-repo/semantics/altIdentifier/url/https://linkinghub.elsevier.com/retrieve/pii/S1386142516307715
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
application/pdf
dc.publisher.none.fl_str_mv Pergamon-Elsevier Science Ltd
publisher.none.fl_str_mv Pergamon-Elsevier Science 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
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score 13.22299

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