Intermolecular interactions in antipyrine-like derivatives 2-halo-: N -(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1 H -pyrazol-4-yl)benzamides: X-ray structure, Hirshfeld surface ana...

Autores: Saeed, Aamer; Khurshid, Asma; Flöerke, Ulrich; Echeverría, Gustavo Alberto; Piro, Oscar Enrique; Gil, Diego Mauricio; Rocha, Mariana; Frontera, Antonio; El-Seedi, Hesham R.; Mumtaz, Amara; Erben, Mauricio Federico
Año de publicación: 2020
Idioma: inglés
Tipo de recurso: artículo
Estado: versión publicada
Descripción: The synthesis, X-ray structure characterization, Hirshfeld surface analysis and DFT calculations of two new antipyrine derivatives are reported herein. Particularly, 2-bromo-N-(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)benzamide (1) and 2-chloro-N-(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)benzamide (2) are synthesized in good yields and characterized spectroscopically. Both compounds are isostructural and crystallize in the monoclinic P21/c space group. The crystal packing of both compounds is mainly stabilized by a combination of N-H⋯O and C-H⋯O hydrogen bonds. In addition, C-H⋯π and lone pair⋯π contacts were observed. Their solid-state structures have been analyzed through Hirshfeld surface analysis, including the evaluation of the different energy frameworks, indicating that the molecular sheets are primarily formed by hydrogen bonds and the stabilization is dominated via the electrostatic energy contribution. These studies are complemented with DFT calculations (B3LYP-D3/def2-TZVP), and a combination of QTAIM/NCIplot analyses disclosing that the H-bonding interactions are energetically relevant (ranging from 0.9 to 6.1 kcal mol-1), however the total binding energies of the different assemblies are dominated by a combination of π-interactions (of the type C-H⋯π, π⋯π, and lone pair halogen⋯π) that are able to stabilize cooperatively the assemblies up to 12 kcal mol-1.
Fil: Saeed, Aamer. Quaid-I-Azam University. Department of Chemistry; Pakistán
Fil: Khurshid, Asma. Quaid-I-Azam University. Department of Chemistry; Pakistán
Fil: Flöerke, Ulrich. Universität Paderborn. Fakultät für Naturwissenschaften. Department Chemie; Alemania
Fil: Echeverría, Gustavo Alberto. 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: Piro, Oscar Enrique. 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: 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. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia; Argentina
Fil: Rocha, Mariana. 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. Universidad Nacional de Tucumán. Facultad de Agronomía y Zootecnia; Argentina
Fil: Frontera, Antonio. Universidad de las Islas Baleares; España
Fil: El-Seedi, Hesham R.. Al-rayan Colleges; Arabia Saudita. Jiangsu University. College of Food and Biological Engineering; China
Fil: Mumtaz, Amara. COMSATS University Islamabad. Department of Chemistry; Pakistán
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: ANTIPYRINE DERIVATES
X-RAY STRUCTURE
NON-COVALENT INTERACTIONS
HIRSHFELD SURFACES
ENERGY FRAMEWORKS
Nivel de accesibilidad: acceso abierto
Condiciones de uso: https://creativecommons.org/licenses/by-nc/2.5/ar/
Repositorio
Institución: Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador: oai:ri.conicet.gov.ar:11336/143344

Acceder

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repository_id_str	3498
network_name_str	CONICET Digital (CONICET)
spelling	Intermolecular interactions in antipyrine-like derivatives 2-halo-: N -(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1 H -pyrazol-4-yl)benzamides: X-ray structure, Hirshfeld surface analysis and DFT calculationsSaeed, AamerKhurshid, AsmaFlöerke, UlrichEcheverría, Gustavo AlbertoPiro, Oscar EnriqueGil, Diego MauricioRocha, MarianaFrontera, AntonioEl-Seedi, Hesham R.Mumtaz, AmaraErben, Mauricio FedericoANTIPYRINE DERIVATESX-RAY STRUCTURENON-COVALENT INTERACTIONSHIRSHFELD SURFACESENERGY FRAMEWORKShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The synthesis, X-ray structure characterization, Hirshfeld surface analysis and DFT calculations of two new antipyrine derivatives are reported herein. Particularly, 2-bromo-N-(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)benzamide (1) and 2-chloro-N-(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)benzamide (2) are synthesized in good yields and characterized spectroscopically. Both compounds are isostructural and crystallize in the monoclinic P21/c space group. The crystal packing of both compounds is mainly stabilized by a combination of N-H⋯O and C-H⋯O hydrogen bonds. In addition, C-H⋯π and lone pair⋯π contacts were observed. Their solid-state structures have been analyzed through Hirshfeld surface analysis, including the evaluation of the different energy frameworks, indicating that the molecular sheets are primarily formed by hydrogen bonds and the stabilization is dominated via the electrostatic energy contribution. These studies are complemented with DFT calculations (B3LYP-D3/def2-TZVP), and a combination of QTAIM/NCIplot analyses disclosing that the H-bonding interactions are energetically relevant (ranging from 0.9 to 6.1 kcal mol-1), however the total binding energies of the different assemblies are dominated by a combination of π-interactions (of the type C-H⋯π, π⋯π, and lone pair halogen⋯π) that are able to stabilize cooperatively the assemblies up to 12 kcal mol-1.Fil: Saeed, Aamer. Quaid-I-Azam University. Department of Chemistry; PakistánFil: Khurshid, Asma. Quaid-I-Azam University. Department of Chemistry; PakistánFil: Flöerke, Ulrich. Universität Paderborn. Fakultät für Naturwissenschaften. Department Chemie; AlemaniaFil: Echeverría, Gustavo Alberto. 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: Piro, Oscar Enrique. 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: 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. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia; ArgentinaFil: Rocha, Mariana. 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. Universidad Nacional de Tucumán. Facultad de Agronomía y Zootecnia; ArgentinaFil: Frontera, Antonio. Universidad de las Islas Baleares; EspañaFil: El-Seedi, Hesham R.. Al-rayan Colleges; Arabia Saudita. Jiangsu University. College of Food and Biological Engineering; ChinaFil: Mumtaz, Amara. COMSATS University Islamabad. Department of Chemistry; PakistánFil: 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"; ArgentinaRoyal Society of Chemistry2020-12info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/143344Saeed, Aamer; Khurshid, Asma; Flöerke, Ulrich; Echeverría, Gustavo Alberto; Piro, Oscar Enrique; et al.; Intermolecular interactions in antipyrine-like derivatives 2-halo-: N -(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1 H -pyrazol-4-yl)benzamides: X-ray structure, Hirshfeld surface analysis and DFT calculations; Royal Society of Chemistry; New Journal of Chemistry; 44; 45; 12-2020; 19541-195541144-05461369-9261CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1039/D0NJ03958Finfo:eu-repo/semantics/altIdentifier/url/https://pubs.rsc.org/en/content/articlelanding/2020/NJ/D0NJ03958Finfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:53:46Zoai:ri.conicet.gov.ar:11336/143344instacron: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 09:53:46.268CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv	Intermolecular interactions in antipyrine-like derivatives 2-halo-: N -(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1 H -pyrazol-4-yl)benzamides: X-ray structure, Hirshfeld surface analysis and DFT calculations
title	Intermolecular interactions in antipyrine-like derivatives 2-halo-: N -(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1 H -pyrazol-4-yl)benzamides: X-ray structure, Hirshfeld surface analysis and DFT calculations
spellingShingle	Intermolecular interactions in antipyrine-like derivatives 2-halo-: N -(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1 H -pyrazol-4-yl)benzamides: X-ray structure, Hirshfeld surface analysis and DFT calculations Saeed, Aamer ANTIPYRINE DERIVATES X-RAY STRUCTURE NON-COVALENT INTERACTIONS HIRSHFELD SURFACES ENERGY FRAMEWORKS
title_short	Intermolecular interactions in antipyrine-like derivatives 2-halo-: N -(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1 H -pyrazol-4-yl)benzamides: X-ray structure, Hirshfeld surface analysis and DFT calculations
title_full	Intermolecular interactions in antipyrine-like derivatives 2-halo-: N -(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1 H -pyrazol-4-yl)benzamides: X-ray structure, Hirshfeld surface analysis and DFT calculations
title_fullStr	Intermolecular interactions in antipyrine-like derivatives 2-halo-: N -(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1 H -pyrazol-4-yl)benzamides: X-ray structure, Hirshfeld surface analysis and DFT calculations
title_full_unstemmed	Intermolecular interactions in antipyrine-like derivatives 2-halo-: N -(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1 H -pyrazol-4-yl)benzamides: X-ray structure, Hirshfeld surface analysis and DFT calculations
title_sort	Intermolecular interactions in antipyrine-like derivatives 2-halo-: N -(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1 H -pyrazol-4-yl)benzamides: X-ray structure, Hirshfeld surface analysis and DFT calculations
dc.creator.none.fl_str_mv	Saeed, Aamer Khurshid, Asma Flöerke, Ulrich Echeverría, Gustavo Alberto Piro, Oscar Enrique Gil, Diego Mauricio Rocha, Mariana Frontera, Antonio El-Seedi, Hesham R. Mumtaz, Amara Erben, Mauricio Federico
author	Saeed, Aamer
author_facet	Saeed, Aamer Khurshid, Asma Flöerke, Ulrich Echeverría, Gustavo Alberto Piro, Oscar Enrique Gil, Diego Mauricio Rocha, Mariana Frontera, Antonio El-Seedi, Hesham R. Mumtaz, Amara Erben, Mauricio Federico
author_role	author
author2	Khurshid, Asma Flöerke, Ulrich Echeverría, Gustavo Alberto Piro, Oscar Enrique Gil, Diego Mauricio Rocha, Mariana Frontera, Antonio El-Seedi, Hesham R. Mumtaz, Amara Erben, Mauricio Federico
author2_role	author author author author author author author author author author
dc.subject.none.fl_str_mv	ANTIPYRINE DERIVATES X-RAY STRUCTURE NON-COVALENT INTERACTIONS HIRSHFELD SURFACES ENERGY FRAMEWORKS
topic	ANTIPYRINE DERIVATES X-RAY STRUCTURE NON-COVALENT INTERACTIONS HIRSHFELD SURFACES ENERGY FRAMEWORKS
purl_subject.fl_str_mv	https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv	The synthesis, X-ray structure characterization, Hirshfeld surface analysis and DFT calculations of two new antipyrine derivatives are reported herein. Particularly, 2-bromo-N-(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)benzamide (1) and 2-chloro-N-(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)benzamide (2) are synthesized in good yields and characterized spectroscopically. Both compounds are isostructural and crystallize in the monoclinic P21/c space group. The crystal packing of both compounds is mainly stabilized by a combination of N-H⋯O and C-H⋯O hydrogen bonds. In addition, C-H⋯π and lone pair⋯π contacts were observed. Their solid-state structures have been analyzed through Hirshfeld surface analysis, including the evaluation of the different energy frameworks, indicating that the molecular sheets are primarily formed by hydrogen bonds and the stabilization is dominated via the electrostatic energy contribution. These studies are complemented with DFT calculations (B3LYP-D3/def2-TZVP), and a combination of QTAIM/NCIplot analyses disclosing that the H-bonding interactions are energetically relevant (ranging from 0.9 to 6.1 kcal mol-1), however the total binding energies of the different assemblies are dominated by a combination of π-interactions (of the type C-H⋯π, π⋯π, and lone pair halogen⋯π) that are able to stabilize cooperatively the assemblies up to 12 kcal mol-1. Fil: Saeed, Aamer. Quaid-I-Azam University. Department of Chemistry; Pakistán Fil: Khurshid, Asma. Quaid-I-Azam University. Department of Chemistry; Pakistán Fil: Flöerke, Ulrich. Universität Paderborn. Fakultät für Naturwissenschaften. Department Chemie; Alemania Fil: Echeverría, Gustavo Alberto. 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: Piro, Oscar Enrique. 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: 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. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia; Argentina Fil: Rocha, Mariana. 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. Universidad Nacional de Tucumán. Facultad de Agronomía y Zootecnia; Argentina Fil: Frontera, Antonio. Universidad de las Islas Baleares; España Fil: El-Seedi, Hesham R.. Al-rayan Colleges; Arabia Saudita. Jiangsu University. College of Food and Biological Engineering; China Fil: Mumtaz, Amara. COMSATS University Islamabad. Department of Chemistry; Pakistán 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	The synthesis, X-ray structure characterization, Hirshfeld surface analysis and DFT calculations of two new antipyrine derivatives are reported herein. Particularly, 2-bromo-N-(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)benzamide (1) and 2-chloro-N-(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)benzamide (2) are synthesized in good yields and characterized spectroscopically. Both compounds are isostructural and crystallize in the monoclinic P21/c space group. The crystal packing of both compounds is mainly stabilized by a combination of N-H⋯O and C-H⋯O hydrogen bonds. In addition, C-H⋯π and lone pair⋯π contacts were observed. Their solid-state structures have been analyzed through Hirshfeld surface analysis, including the evaluation of the different energy frameworks, indicating that the molecular sheets are primarily formed by hydrogen bonds and the stabilization is dominated via the electrostatic energy contribution. These studies are complemented with DFT calculations (B3LYP-D3/def2-TZVP), and a combination of QTAIM/NCIplot analyses disclosing that the H-bonding interactions are energetically relevant (ranging from 0.9 to 6.1 kcal mol-1), however the total binding energies of the different assemblies are dominated by a combination of π-interactions (of the type C-H⋯π, π⋯π, and lone pair halogen⋯π) that are able to stabilize cooperatively the assemblies up to 12 kcal mol-1.
publishDate	2020
dc.date.none.fl_str_mv	2020-12
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/11336/143344 Saeed, Aamer; Khurshid, Asma; Flöerke, Ulrich; Echeverría, Gustavo Alberto; Piro, Oscar Enrique; et al.; Intermolecular interactions in antipyrine-like derivatives 2-halo-: N -(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1 H -pyrazol-4-yl)benzamides: X-ray structure, Hirshfeld surface analysis and DFT calculations; Royal Society of Chemistry; New Journal of Chemistry; 44; 45; 12-2020; 19541-19554 1144-0546 1369-9261 CONICET Digital CONICET
url	http://hdl.handle.net/11336/143344
identifier_str_mv	Saeed, Aamer; Khurshid, Asma; Flöerke, Ulrich; Echeverría, Gustavo Alberto; Piro, Oscar Enrique; et al.; Intermolecular interactions in antipyrine-like derivatives 2-halo-: N -(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1 H -pyrazol-4-yl)benzamides: X-ray structure, Hirshfeld surface analysis and DFT calculations; Royal Society of Chemistry; New Journal of Chemistry; 44; 45; 12-2020; 19541-19554 1144-0546 1369-9261 CONICET Digital CONICET
dc.language.none.fl_str_mv	eng
language	eng
dc.relation.none.fl_str_mv	info:eu-repo/semantics/altIdentifier/doi/10.1039/D0NJ03958F info:eu-repo/semantics/altIdentifier/url/https://pubs.rsc.org/en/content/articlelanding/2020/NJ/D0NJ03958F
dc.rights.none.fl_str_mv	info:eu-repo/semantics/openAccess https://creativecommons.org/licenses/by-nc/2.5/ar/
eu_rights_str_mv	openAccess
rights_invalid_str_mv	https://creativecommons.org/licenses/by-nc/2.5/ar/
dc.format.none.fl_str_mv	application/pdf application/pdf
dc.publisher.none.fl_str_mv	Royal Society of Chemistry
publisher.none.fl_str_mv	Royal Society of Chemistry
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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Intermolecular interactions in antipyrine-like derivatives 2-halo-: N -(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1 H -pyrazol-4-yl)benzamides: X-ray structure, Hirshfeld surface ana...

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