Weak interactions in cocrystals of isoniazid with glycolic and mandelic acids

Autores
Álvarez-Vidaurre, Raquel; Castiñeiras, Alfonso; Frontera, Antonio; García Santos, Isabel; Gil, Diego Mauricio; González Pérez, Josefa M.; Niclós Gutiérrez, Juan; Torres Iglesias, Rocío
Año de publicación
2021
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
This work deals with the preparation of pyridine-3-carbohydrazide (isoniazid, inh) cocrystals with two α-hydroxycarboxylic acids. The interaction of glycolic acid (H2ga) or d,l-mandelic acid (H2ma) resulted in the formation of cocrystals or salts of composition (inh) (H2ga) (1) and [Hinh]+[Hma]-. (H2ma) (2) when reacted with isoniazid. An N0-(propan-2-ylidene)isonicotinic hydrazide hemihydrate, (pinh).1/2(H2O) (3), was also prepared by condensation of isoniazid with acetone in the presence of glycolic acid. These prepared compounds were well characterized by elemental analysis, and spectroscopic methods, and their three-dimensional molecular structure was determined by single crystal X-ray crystallography. Hydrogen bonds involving the carboxylic acid occur consistently with the pyridine ring N atom of the isoniazid and its derivatives. The remaining hydrogen-bonding sites on the isoniazid backbone vary based on the steric influences of the derivative group. These are contrasted in each of the molecular systems. Finally, Hirshfeld surface analysis and Density-functional theory (DFT) calculations (including NCIplot and QTAIM analyses) have been performed to further characterize and rationalize the non-covalent interactions.
Fil: Álvarez-Vidaurre, Raquel. Universidad de Santiago de Compostela; España
Fil: Castiñeiras, Alfonso. Universidad de Santiago de Compostela; España
Fil: Frontera, Antonio. Universidad de las Islas Baleares; España
Fil: García Santos, Isabel. 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: González Pérez, Josefa M.. Universidad de Granada; España
Fil: Niclós Gutiérrez, Juan. Universidad de Granada; España
Fil: Torres Iglesias, Rocío. Universidad de Santiago de Compostela; España
Materia
COCRYSTALS
DFT CALCULATIONS
DL-MANDELIC ACID
GLYCOLIC ACID
HIRSHFELD SURFACE ANALYSIS
ISONIAZID
X-RAY STRUCTURE
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/153836
Acceder
id CONICETDig_31b5200ec8c975781e3b0a4c6ce8b134
oai_identifier_str oai:ri.conicet.gov.ar:11336/153836
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Weak interactions in cocrystals of isoniazid with glycolic and mandelic acidsÁlvarez-Vidaurre, RaquelCastiñeiras, AlfonsoFrontera, AntonioGarcía Santos, IsabelGil, Diego MauricioGonzález Pérez, Josefa M.Niclós Gutiérrez, JuanTorres Iglesias, RocíoCOCRYSTALSDFT CALCULATIONSDL-MANDELIC ACIDGLYCOLIC ACIDHIRSHFELD SURFACE ANALYSISISONIAZIDX-RAY STRUCTUREhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1This work deals with the preparation of pyridine-3-carbohydrazide (isoniazid, inh) cocrystals with two α-hydroxycarboxylic acids. The interaction of glycolic acid (H2ga) or d,l-mandelic acid (H2ma) resulted in the formation of cocrystals or salts of composition (inh) (H2ga) (1) and [Hinh]+[Hma]-. (H2ma) (2) when reacted with isoniazid. An N0-(propan-2-ylidene)isonicotinic hydrazide hemihydrate, (pinh).1/2(H2O) (3), was also prepared by condensation of isoniazid with acetone in the presence of glycolic acid. These prepared compounds were well characterized by elemental analysis, and spectroscopic methods, and their three-dimensional molecular structure was determined by single crystal X-ray crystallography. Hydrogen bonds involving the carboxylic acid occur consistently with the pyridine ring N atom of the isoniazid and its derivatives. The remaining hydrogen-bonding sites on the isoniazid backbone vary based on the steric influences of the derivative group. These are contrasted in each of the molecular systems. Finally, Hirshfeld surface analysis and Density-functional theory (DFT) calculations (including NCIplot and QTAIM analyses) have been performed to further characterize and rationalize the non-covalent interactions.Fil: Álvarez-Vidaurre, Raquel. Universidad de Santiago de Compostela; EspañaFil: Castiñeiras, Alfonso. Universidad de Santiago de Compostela; EspañaFil: Frontera, Antonio. Universidad de las Islas Baleares; EspañaFil: García Santos, Isabel. 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: González Pérez, Josefa M.. Universidad de Granada; EspañaFil: Niclós Gutiérrez, Juan. Universidad de Granada; EspañaFil: Torres Iglesias, Rocío. Universidad de Santiago de Compostela; EspañaMDPI AG2021-03info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/153836Álvarez-Vidaurre, Raquel; Castiñeiras, Alfonso; Frontera, Antonio; García Santos, Isabel; Gil, Diego Mauricio; et al.; Weak interactions in cocrystals of isoniazid with glycolic and mandelic acids; MDPI AG; Crystals; 11; 4; 3-2021; 1-222073-43522073-4352CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.3390/cryst11040328info:eu-repo/semantics/altIdentifier/url/https://www.mdpi.com/2073-4352/11/4/328info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:33:49Zoai:ri.conicet.gov.ar:11336/153836instacron: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 10:33:49.662CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Weak interactions in cocrystals of isoniazid with glycolic and mandelic acids
title Weak interactions in cocrystals of isoniazid with glycolic and mandelic acids
spellingShingle Weak interactions in cocrystals of isoniazid with glycolic and mandelic acids
Álvarez-Vidaurre, Raquel
COCRYSTALS
DFT CALCULATIONS
DL-MANDELIC ACID
GLYCOLIC ACID
HIRSHFELD SURFACE ANALYSIS
ISONIAZID
X-RAY STRUCTURE
title_short Weak interactions in cocrystals of isoniazid with glycolic and mandelic acids
title_full Weak interactions in cocrystals of isoniazid with glycolic and mandelic acids
title_fullStr Weak interactions in cocrystals of isoniazid with glycolic and mandelic acids
title_full_unstemmed Weak interactions in cocrystals of isoniazid with glycolic and mandelic acids
title_sort Weak interactions in cocrystals of isoniazid with glycolic and mandelic acids
dc.creator.none.fl_str_mv Álvarez-Vidaurre, Raquel
Castiñeiras, Alfonso
Frontera, Antonio
García Santos, Isabel
Gil, Diego Mauricio
González Pérez, Josefa M.
Niclós Gutiérrez, Juan
Torres Iglesias, Rocío
author Álvarez-Vidaurre, Raquel
author_facet Álvarez-Vidaurre, Raquel
Castiñeiras, Alfonso
Frontera, Antonio
García Santos, Isabel
Gil, Diego Mauricio
González Pérez, Josefa M.
Niclós Gutiérrez, Juan
Torres Iglesias, Rocío
author_role author
author2 Castiñeiras, Alfonso
Frontera, Antonio
García Santos, Isabel
Gil, Diego Mauricio
González Pérez, Josefa M.
Niclós Gutiérrez, Juan
Torres Iglesias, Rocío
author2_role author
author
author
author
author
author
author
dc.subject.none.fl_str_mv COCRYSTALS
DFT CALCULATIONS
DL-MANDELIC ACID
GLYCOLIC ACID
HIRSHFELD SURFACE ANALYSIS
ISONIAZID
X-RAY STRUCTURE
topic COCRYSTALS
DFT CALCULATIONS
DL-MANDELIC ACID
GLYCOLIC ACID
HIRSHFELD SURFACE ANALYSIS
ISONIAZID
X-RAY STRUCTURE
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv This work deals with the preparation of pyridine-3-carbohydrazide (isoniazid, inh) cocrystals with two α-hydroxycarboxylic acids. The interaction of glycolic acid (H2ga) or d,l-mandelic acid (H2ma) resulted in the formation of cocrystals or salts of composition (inh) (H2ga) (1) and [Hinh]+[Hma]-. (H2ma) (2) when reacted with isoniazid. An N0-(propan-2-ylidene)isonicotinic hydrazide hemihydrate, (pinh).1/2(H2O) (3), was also prepared by condensation of isoniazid with acetone in the presence of glycolic acid. These prepared compounds were well characterized by elemental analysis, and spectroscopic methods, and their three-dimensional molecular structure was determined by single crystal X-ray crystallography. Hydrogen bonds involving the carboxylic acid occur consistently with the pyridine ring N atom of the isoniazid and its derivatives. The remaining hydrogen-bonding sites on the isoniazid backbone vary based on the steric influences of the derivative group. These are contrasted in each of the molecular systems. Finally, Hirshfeld surface analysis and Density-functional theory (DFT) calculations (including NCIplot and QTAIM analyses) have been performed to further characterize and rationalize the non-covalent interactions.
Fil: Álvarez-Vidaurre, Raquel. Universidad de Santiago de Compostela; España
Fil: Castiñeiras, Alfonso. Universidad de Santiago de Compostela; España
Fil: Frontera, Antonio. Universidad de las Islas Baleares; España
Fil: García Santos, Isabel. 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: González Pérez, Josefa M.. Universidad de Granada; España
Fil: Niclós Gutiérrez, Juan. Universidad de Granada; España
Fil: Torres Iglesias, Rocío. Universidad de Santiago de Compostela; España
description This work deals with the preparation of pyridine-3-carbohydrazide (isoniazid, inh) cocrystals with two α-hydroxycarboxylic acids. The interaction of glycolic acid (H2ga) or d,l-mandelic acid (H2ma) resulted in the formation of cocrystals or salts of composition (inh) (H2ga) (1) and [Hinh]+[Hma]-. (H2ma) (2) when reacted with isoniazid. An N0-(propan-2-ylidene)isonicotinic hydrazide hemihydrate, (pinh).1/2(H2O) (3), was also prepared by condensation of isoniazid with acetone in the presence of glycolic acid. These prepared compounds were well characterized by elemental analysis, and spectroscopic methods, and their three-dimensional molecular structure was determined by single crystal X-ray crystallography. Hydrogen bonds involving the carboxylic acid occur consistently with the pyridine ring N atom of the isoniazid and its derivatives. The remaining hydrogen-bonding sites on the isoniazid backbone vary based on the steric influences of the derivative group. These are contrasted in each of the molecular systems. Finally, Hirshfeld surface analysis and Density-functional theory (DFT) calculations (including NCIplot and QTAIM analyses) have been performed to further characterize and rationalize the non-covalent interactions.
publishDate 2021
dc.date.none.fl_str_mv 2021-03
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/11336/153836
Álvarez-Vidaurre, Raquel; Castiñeiras, Alfonso; Frontera, Antonio; García Santos, Isabel; Gil, Diego Mauricio; et al.; Weak interactions in cocrystals of isoniazid with glycolic and mandelic acids; MDPI AG; Crystals; 11; 4; 3-2021; 1-22
2073-4352
2073-4352
CONICET Digital
CONICET
url http://hdl.handle.net/11336/153836
identifier_str_mv Álvarez-Vidaurre, Raquel; Castiñeiras, Alfonso; Frontera, Antonio; García Santos, Isabel; Gil, Diego Mauricio; et al.; Weak interactions in cocrystals of isoniazid with glycolic and mandelic acids; MDPI AG; Crystals; 11; 4; 3-2021; 1-22
2073-4352
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.3390/cryst11040328
info:eu-repo/semantics/altIdentifier/url/https://www.mdpi.com/2073-4352/11/4/328
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv MDPI AG
publisher.none.fl_str_mv MDPI AG
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 13.070432

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