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
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/153874
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CONICET Digital (CONICET) |
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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 Técnicas2025-09-29T09:37:09Zoai: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:34982025-09-29 09:37:09.508CONICET 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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1844613169157242881 |
score |
13.070432 |