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
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/65408
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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 Técnicas2025-09-29T09:46:04Zoai: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:34982025-09-29 09:46:04.612CONICET 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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1844613439487475712 |
score |
13.070432 |