Supramolecular, spectroscopic and computational analysis of weak interactions in some thiosemicarbazones derived from 5-acetylbarbituric acid

Autores
Castiñeiras, Alfonso; Fernández Hermida, Nuria; García Santos, Isabel; Gómez Rodríguez, Lourdes; Gil, Diego Mauricio; Frontera, Antonio
Año de publicación
2021
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A new series of 5-acetylbarbituric based thiosemicarbazones (TSC) named 5-acetylbarbituric hydrazine-1-carbothioamide (1), N-methyl-(5-acetylbarbituric)hydrazine-1-carbothioamide (2), N-ethyl-(5-acetylbarbituric)hydrazine-1-carbothioamide (3), N,N-dimethyl-(5-acetylbarbituric)hydrazine-1-carbothioamide (4), N'-piperidine-(5-acetylbarbituric)-1-carbothiohydrazide (5) and N'-hexamethyleneimine-(5-acetylbarbituric)-1-carbothiohydrazide (6), has been synthesized from 5-acetylbarbituric acid and N-unsubstituted/substituted thiosemicarbazides. The synthesized compounds were well characterized by elemental analyses, FT-IR, 1H, 13C NMR and mass spectroscopic methods. Three-dimensional molecular structures of three compounds (1⋅DMSO, 2 and 6⋅H2O) were determined by single crystal X-ray crystallography, and an analysis of their supramolecular structure was carried out. The supramolecular features of the X-ray structure were also studied using Hirshfeld surface analysis. Finally, H-bonding networks observed in the solid state X-ray structures of 1⋅DMSO, 2, and 6⋅H2O and unconventional π-stacking dimers in 6⋅H2O were further analyzed by DFT calculations in combination with molecular electrostatic potential surfaces and combined QTAIM/NCIplot computational tools.
Fil: Castiñeiras, Alfonso. Universidad de Santiago de Compostela; España
Fil: Fernández Hermida, Nuria. Universidad de Santiago de Compostela; España
Fil: García Santos, Isabel. Universidad de Santiago de Compostela; España
Fil: Gómez Rodríguez, Lourdes. Universidad de Santiago de Compostela; España
Fil: Gil, Diego Mauricio. Universidad Nacional de Tucumán. Instituto de Biotecnología Farmacéutica y Alimentaria. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Biotecnología Farmacéutica y Alimentaria; Argentina
Fil: Frontera, Antonio. Universidad de las Islas Baleares; España
Materia
5-ACETYLBARBITURIC ACID
CRYSTAL STRUCTURE
DFT CALCULATIONS
HETEROCYCLES
HIRSHFELD SURFACE
THIOSEMICARBAZONES
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/153874
Acceder
id CONICETDig_245eda4ebe55950032baf07fdc249160
oai_identifier_str oai:ri.conicet.gov.ar:11336/153874
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Supramolecular, spectroscopic and computational analysis of weak interactions in some thiosemicarbazones derived from 5-acetylbarbituric acidCastiñeiras, AlfonsoFernández Hermida, NuriaGarcía Santos, IsabelGómez Rodríguez, LourdesGil, Diego MauricioFrontera, Antonio5-ACETYLBARBITURIC ACIDCRYSTAL STRUCTUREDFT CALCULATIONSHETEROCYCLESHIRSHFELD SURFACETHIOSEMICARBAZONEShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A new series of 5-acetylbarbituric based thiosemicarbazones (TSC) named 5-acetylbarbituric hydrazine-1-carbothioamide (1), N-methyl-(5-acetylbarbituric)hydrazine-1-carbothioamide (2), N-ethyl-(5-acetylbarbituric)hydrazine-1-carbothioamide (3), N,N-dimethyl-(5-acetylbarbituric)hydrazine-1-carbothioamide (4), N'-piperidine-(5-acetylbarbituric)-1-carbothiohydrazide (5) and N'-hexamethyleneimine-(5-acetylbarbituric)-1-carbothiohydrazide (6), has been synthesized from 5-acetylbarbituric acid and N-unsubstituted/substituted thiosemicarbazides. The synthesized compounds were well characterized by elemental analyses, FT-IR, 1H, 13C NMR and mass spectroscopic methods. Three-dimensional molecular structures of three compounds (1⋅DMSO, 2 and 6⋅H2O) were determined by single crystal X-ray crystallography, and an analysis of their supramolecular structure was carried out. The supramolecular features of the X-ray structure were also studied using Hirshfeld surface analysis. Finally, H-bonding networks observed in the solid state X-ray structures of 1⋅DMSO, 2, and 6⋅H2O and unconventional π-stacking dimers in 6⋅H2O were further analyzed by DFT calculations in combination with molecular electrostatic potential surfaces and combined QTAIM/NCIplot computational tools.Fil: Castiñeiras, Alfonso. Universidad de Santiago de Compostela; EspañaFil: Fernández Hermida, Nuria. Universidad de Santiago de Compostela; EspañaFil: García Santos, Isabel. Universidad de Santiago de Compostela; EspañaFil: Gómez Rodríguez, Lourdes. Universidad de Santiago de Compostela; EspañaFil: Gil, Diego Mauricio. Universidad Nacional de Tucumán. Instituto de Biotecnología Farmacéutica y Alimentaria. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Biotecnología Farmacéutica y Alimentaria; ArgentinaFil: Frontera, Antonio. Universidad de las Islas Baleares; EspañaElsevier Science2021-12info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/153874Castiñeiras, Alfonso; Fernández Hermida, Nuria; García Santos, Isabel; Gómez Rodríguez, Lourdes; Gil, Diego Mauricio; et al.; Supramolecular, spectroscopic and computational analysis of weak interactions in some thiosemicarbazones derived from 5-acetylbarbituric acid; Elsevier Science; Journal of Molecular Structure; 1245; 12-2021; 1-140022-28601872-8014CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.molstruc.2021.131031info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0022286021011637info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-22T11:05:17Zoai:ri.conicet.gov.ar:11336/153874instacron: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:34982025-10-22 11:05:18.006CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Supramolecular, spectroscopic and computational analysis of weak interactions in some thiosemicarbazones derived from 5-acetylbarbituric acid
title Supramolecular, spectroscopic and computational analysis of weak interactions in some thiosemicarbazones derived from 5-acetylbarbituric acid
spellingShingle Supramolecular, spectroscopic and computational analysis of weak interactions in some thiosemicarbazones derived from 5-acetylbarbituric acid
Castiñeiras, Alfonso
5-ACETYLBARBITURIC ACID
CRYSTAL STRUCTURE
DFT CALCULATIONS
HETEROCYCLES
HIRSHFELD SURFACE
THIOSEMICARBAZONES
title_short Supramolecular, spectroscopic and computational analysis of weak interactions in some thiosemicarbazones derived from 5-acetylbarbituric acid
title_full Supramolecular, spectroscopic and computational analysis of weak interactions in some thiosemicarbazones derived from 5-acetylbarbituric acid
title_fullStr Supramolecular, spectroscopic and computational analysis of weak interactions in some thiosemicarbazones derived from 5-acetylbarbituric acid
title_full_unstemmed Supramolecular, spectroscopic and computational analysis of weak interactions in some thiosemicarbazones derived from 5-acetylbarbituric acid
title_sort Supramolecular, spectroscopic and computational analysis of weak interactions in some thiosemicarbazones derived from 5-acetylbarbituric acid
dc.creator.none.fl_str_mv Castiñeiras, Alfonso
Fernández Hermida, Nuria
García Santos, Isabel
Gómez Rodríguez, Lourdes
Gil, Diego Mauricio
Frontera, Antonio
author Castiñeiras, Alfonso
author_facet Castiñeiras, Alfonso
Fernández Hermida, Nuria
García Santos, Isabel
Gómez Rodríguez, Lourdes
Gil, Diego Mauricio
Frontera, Antonio
author_role author
author2 Fernández Hermida, Nuria
García Santos, Isabel
Gómez Rodríguez, Lourdes
Gil, Diego Mauricio
Frontera, Antonio
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv 5-ACETYLBARBITURIC ACID
CRYSTAL STRUCTURE
DFT CALCULATIONS
HETEROCYCLES
HIRSHFELD SURFACE
THIOSEMICARBAZONES
topic 5-ACETYLBARBITURIC ACID
CRYSTAL STRUCTURE
DFT CALCULATIONS
HETEROCYCLES
HIRSHFELD SURFACE
THIOSEMICARBAZONES
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv A new series of 5-acetylbarbituric based thiosemicarbazones (TSC) named 5-acetylbarbituric hydrazine-1-carbothioamide (1), N-methyl-(5-acetylbarbituric)hydrazine-1-carbothioamide (2), N-ethyl-(5-acetylbarbituric)hydrazine-1-carbothioamide (3), N,N-dimethyl-(5-acetylbarbituric)hydrazine-1-carbothioamide (4), N'-piperidine-(5-acetylbarbituric)-1-carbothiohydrazide (5) and N'-hexamethyleneimine-(5-acetylbarbituric)-1-carbothiohydrazide (6), has been synthesized from 5-acetylbarbituric acid and N-unsubstituted/substituted thiosemicarbazides. The synthesized compounds were well characterized by elemental analyses, FT-IR, 1H, 13C NMR and mass spectroscopic methods. Three-dimensional molecular structures of three compounds (1⋅DMSO, 2 and 6⋅H2O) were determined by single crystal X-ray crystallography, and an analysis of their supramolecular structure was carried out. The supramolecular features of the X-ray structure were also studied using Hirshfeld surface analysis. Finally, H-bonding networks observed in the solid state X-ray structures of 1⋅DMSO, 2, and 6⋅H2O and unconventional π-stacking dimers in 6⋅H2O were further analyzed by DFT calculations in combination with molecular electrostatic potential surfaces and combined QTAIM/NCIplot computational tools.
Fil: Castiñeiras, Alfonso. Universidad de Santiago de Compostela; España
Fil: Fernández Hermida, Nuria. Universidad de Santiago de Compostela; España
Fil: García Santos, Isabel. Universidad de Santiago de Compostela; España
Fil: Gómez Rodríguez, Lourdes. Universidad de Santiago de Compostela; España
Fil: Gil, Diego Mauricio. Universidad Nacional de Tucumán. Instituto de Biotecnología Farmacéutica y Alimentaria. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Biotecnología Farmacéutica y Alimentaria; Argentina
Fil: Frontera, Antonio. Universidad de las Islas Baleares; España
description A new series of 5-acetylbarbituric based thiosemicarbazones (TSC) named 5-acetylbarbituric hydrazine-1-carbothioamide (1), N-methyl-(5-acetylbarbituric)hydrazine-1-carbothioamide (2), N-ethyl-(5-acetylbarbituric)hydrazine-1-carbothioamide (3), N,N-dimethyl-(5-acetylbarbituric)hydrazine-1-carbothioamide (4), N'-piperidine-(5-acetylbarbituric)-1-carbothiohydrazide (5) and N'-hexamethyleneimine-(5-acetylbarbituric)-1-carbothiohydrazide (6), has been synthesized from 5-acetylbarbituric acid and N-unsubstituted/substituted thiosemicarbazides. The synthesized compounds were well characterized by elemental analyses, FT-IR, 1H, 13C NMR and mass spectroscopic methods. Three-dimensional molecular structures of three compounds (1⋅DMSO, 2 and 6⋅H2O) were determined by single crystal X-ray crystallography, and an analysis of their supramolecular structure was carried out. The supramolecular features of the X-ray structure were also studied using Hirshfeld surface analysis. Finally, H-bonding networks observed in the solid state X-ray structures of 1⋅DMSO, 2, and 6⋅H2O and unconventional π-stacking dimers in 6⋅H2O were further analyzed by DFT calculations in combination with molecular electrostatic potential surfaces and combined QTAIM/NCIplot computational tools.
publishDate 2021
dc.date.none.fl_str_mv 2021-12
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/11336/153874
Castiñeiras, Alfonso; Fernández Hermida, Nuria; García Santos, Isabel; Gómez Rodríguez, Lourdes; Gil, Diego Mauricio; et al.; Supramolecular, spectroscopic and computational analysis of weak interactions in some thiosemicarbazones derived from 5-acetylbarbituric acid; Elsevier Science; Journal of Molecular Structure; 1245; 12-2021; 1-14
0022-2860
1872-8014
CONICET Digital
CONICET
url http://hdl.handle.net/11336/153874
identifier_str_mv Castiñeiras, Alfonso; Fernández Hermida, Nuria; García Santos, Isabel; Gómez Rodríguez, Lourdes; Gil, Diego Mauricio; et al.; Supramolecular, spectroscopic and computational analysis of weak interactions in some thiosemicarbazones derived from 5-acetylbarbituric acid; Elsevier Science; Journal of Molecular Structure; 1245; 12-2021; 1-14
0022-2860
1872-8014
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.molstruc.2021.131031
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0022286021011637
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier Science
publisher.none.fl_str_mv Elsevier Science
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 12.982451

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