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

Autores
Ramos Cairo, Raúl; Plutín Stevens, Ana María; Oliveira, Tamires D.; 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 Nsingle bondH ⋯ Odouble bondC 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 — H ⋯ O = C hydrogen bond forming R22(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.
Instituto de Física La Plata
Centro de Química Inorgánica
Materia
Química
Thiourea derivatives
Molecular conformation
Single crystal structure determination
Vibrational spectroscopy
Hirshfeld surface analysis
Topological study
Nivel de accesibilidad
acceso abierto
Condiciones de uso
http://creativecommons.org/licenses/by-nc-sa/4.0/
Repositorio
SEDICI (UNLP)
Institución
Universidad Nacional de La Plata
OAI Identificador
oai:sedici.unlp.edu.ar:10915/104881

id SEDICI_4f79c304810fd7a6022c378ad98487c7
oai_identifier_str oai:sedici.unlp.edu.ar:10915/104881
network_acronym_str SEDICI
repository_id_str 1329
network_name_str SEDICI (UNLP)
spelling Understanding the conformational changes and molecular structure of furoyl thioureas upon substitutionRamos Cairo, RaúlPlutín Stevens, Ana MaríaOliveira, Tamires D.Batista, Alzir A.Castellano, Eduardo E.Duque, JulioSoria, Delia BeatrizFantoni, Adolfo CarlosCorrêa, Rodrigo S.Erben, Mauricio FedericoQuímicaThiourea derivativesMolecular conformationSingle crystal structure determinationVibrational spectroscopyHirshfeld surface analysisTopological study1-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 Nsingle bondH ⋯ Odouble bondC 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 — H ⋯ O = C hydrogen bond forming R22(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.Instituto de Física La PlataCentro de Química Inorgánica2017-04info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionArticulohttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdf8-17http://sedici.unlp.edu.ar/handle/10915/104881enginfo:eu-repo/semantics/altIdentifier/issn/1386-1425info:eu-repo/semantics/altIdentifier/doi/10.1016/j.saa.2016.12.038info:eu-repo/semantics/openAccesshttp://creativecommons.org/licenses/by-nc-sa/4.0/Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International (CC BY-NC-SA 4.0)reponame:SEDICI (UNLP)instname:Universidad Nacional de La Platainstacron:UNLP2025-09-29T11:22:57Zoai:sedici.unlp.edu.ar:10915/104881Institucionalhttp://sedici.unlp.edu.ar/Universidad públicaNo correspondehttp://sedici.unlp.edu.ar/oai/snrdalira@sedici.unlp.edu.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:13292025-09-29 11:22:58.183SEDICI (UNLP) - Universidad Nacional de La Platafalse
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
Química
Thiourea derivatives
Molecular conformation
Single crystal structure determination
Vibrational spectroscopy
Hirshfeld surface analysis
Topological study
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
Oliveira, Tamires D.
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
Oliveira, Tamires D.
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
Oliveira, Tamires D.
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 Química
Thiourea derivatives
Molecular conformation
Single crystal structure determination
Vibrational spectroscopy
Hirshfeld surface analysis
Topological study
topic Química
Thiourea derivatives
Molecular conformation
Single crystal structure determination
Vibrational spectroscopy
Hirshfeld surface analysis
Topological study
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 Nsingle bondH ⋯ Odouble bondC 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 — H ⋯ O = C hydrogen bond forming R22(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.
Instituto de Física La Plata
Centro de Química Inorgánica
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 Nsingle bondH ⋯ Odouble bondC 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 — H ⋯ O = C hydrogen bond forming R22(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
Articulo
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://sedici.unlp.edu.ar/handle/10915/104881
url http://sedici.unlp.edu.ar/handle/10915/104881
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/issn/1386-1425
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.saa.2016.12.038
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by-nc-sa/4.0/
Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International (CC BY-NC-SA 4.0)
eu_rights_str_mv openAccess
rights_invalid_str_mv http://creativecommons.org/licenses/by-nc-sa/4.0/
Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International (CC BY-NC-SA 4.0)
dc.format.none.fl_str_mv application/pdf
8-17
dc.source.none.fl_str_mv reponame:SEDICI (UNLP)
instname:Universidad Nacional de La Plata
instacron:UNLP
reponame_str SEDICI (UNLP)
collection SEDICI (UNLP)
instname_str Universidad Nacional de La Plata
instacron_str UNLP
institution UNLP
repository.name.fl_str_mv SEDICI (UNLP) - Universidad Nacional de La Plata
repository.mail.fl_str_mv alira@sedici.unlp.edu.ar
_version_ 1844616105709010944
score 13.070432