Recurrent π-π stacking motifs in three new 4,5-dihydropyrazolyl-thiazole-coumarin hybrids: X-ray characterization, Hirshfeld surface analysis and DFT calculations

Autores
Madni, Murtaza; Ahmed, Muhammad Naeem; Hafeez, Muhammad; Ashfaq, Muhammad; Tahir, Muhammad Nawaz; Gil, Diego Mauricio; Galmés, Bartomeu; Hameed, Shahid; Frontera, Antonio
Año de publicación
2020
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The synthesis and X-ray characterization of three new 4,5-dihydropyrazolylthiazole-coumarin hybrids (1-3) are reported herein, namely 3-(2-(3,5-bis(4-chlorophenyl)-4,5-dihydropyrazol-1-yl)thiazol-4-yl)-2H-chromen-2-one (1), 3-(2-(5-(4-chlorophenyl)-4,5-dihydro-3-phenylpyrazol-1-yl)thiazol-4-yl)-2H-chromen-2-one (2) and 3-(2-(3-(4-chlorophenyl)-4,5-dihydro-5-p-tolylpyrazol-1-yl)thiazol-4-yl)-2H-chromen-2-one (3). A detailed structural analysis of the noncovalent interactions and their evaluation using Hirshfeld surface analysis is also reported, evidencing the importance of C-H⋯O and π-π interactions. Finally, DFT calculations along with the molecular electrostatic potential (MEP) and NCIplot index analysis have been used to evaluate those interactions energetically and to investigate the relative importance of two different π-stacking modes that are recurrent binding motifs in the solid state architecture of the three complexes.
Fil: Madni, Murtaza. Quaiad-i-Azam University; Pakistán
Fil: Ahmed, Muhammad Naeem. University of Azad Jammu and Kashmir; Pakistán
Fil: Hafeez, Muhammad. University of Azad Jammu and Kashmir; Pakistán
Fil: Ashfaq, Muhammad. University of Sargodha; Pakistán
Fil: Tahir, Muhammad Nawaz. University of Sargodha; Pakistán
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. Instituto de Química Orgánica; Argentina
Fil: Galmés, Bartomeu. Universidad de las Islas Baleares; España
Fil: Hameed, Shahid. Quaiad-i-Azam University; Pakistán
Fil: Frontera, Antonio. Universidad de las Islas Baleares; España
Materia
COUMARIN
INTERMOLECULAR INTERACTIONS
DFT
HIRSHFELD SURFACES
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/143346
Acceder
id CONICETDig_82e928175faec07753c4100f07d32b63
oai_identifier_str oai:ri.conicet.gov.ar:11336/143346
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Recurrent π-π stacking motifs in three new 4,5-dihydropyrazolyl-thiazole-coumarin hybrids: X-ray characterization, Hirshfeld surface analysis and DFT calculationsMadni, MurtazaAhmed, Muhammad NaeemHafeez, MuhammadAshfaq, MuhammadTahir, Muhammad NawazGil, Diego MauricioGalmés, BartomeuHameed, ShahidFrontera, AntonioCOUMARININTERMOLECULAR INTERACTIONSDFTHIRSHFELD SURFACEShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The synthesis and X-ray characterization of three new 4,5-dihydropyrazolylthiazole-coumarin hybrids (1-3) are reported herein, namely 3-(2-(3,5-bis(4-chlorophenyl)-4,5-dihydropyrazol-1-yl)thiazol-4-yl)-2H-chromen-2-one (1), 3-(2-(5-(4-chlorophenyl)-4,5-dihydro-3-phenylpyrazol-1-yl)thiazol-4-yl)-2H-chromen-2-one (2) and 3-(2-(3-(4-chlorophenyl)-4,5-dihydro-5-p-tolylpyrazol-1-yl)thiazol-4-yl)-2H-chromen-2-one (3). A detailed structural analysis of the noncovalent interactions and their evaluation using Hirshfeld surface analysis is also reported, evidencing the importance of C-H⋯O and π-π interactions. Finally, DFT calculations along with the molecular electrostatic potential (MEP) and NCIplot index analysis have been used to evaluate those interactions energetically and to investigate the relative importance of two different π-stacking modes that are recurrent binding motifs in the solid state architecture of the three complexes.Fil: Madni, Murtaza. Quaiad-i-Azam University; PakistánFil: Ahmed, Muhammad Naeem. University of Azad Jammu and Kashmir; PakistánFil: Hafeez, Muhammad. University of Azad Jammu and Kashmir; PakistánFil: Ashfaq, Muhammad. University of Sargodha; PakistánFil: Tahir, Muhammad Nawaz. University of Sargodha; PakistánFil: 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. Instituto de Química Orgánica; ArgentinaFil: Galmés, Bartomeu. Universidad de las Islas Baleares; EspañaFil: Hameed, Shahid. Quaiad-i-Azam University; PakistánFil: Frontera, Antonio. Universidad de las Islas Baleares; EspañaRoyal Society of Chemistry2020-09info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/143346Madni, Murtaza; Ahmed, Muhammad Naeem; Hafeez, Muhammad; Ashfaq, Muhammad; Tahir, Muhammad Nawaz; et al.; Recurrent π-π stacking motifs in three new 4,5-dihydropyrazolyl-thiazole-coumarin hybrids: X-ray characterization, Hirshfeld surface analysis and DFT calculations; Royal Society of Chemistry; New Journal of Chemistry; 44; 34; 9-2020; 14592-146031144-05461369-9261CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://pubs.rsc.org/en/Content/ArticleLanding/2020/NJ/D0NJ02931Ainfo:eu-repo/semantics/altIdentifier/doi/10.1039/D0NJ02931Ainfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T15:14:53Zoai:ri.conicet.gov.ar:11336/143346instacron: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:34982025-10-15 15:14:53.859CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Recurrent π-π stacking motifs in three new 4,5-dihydropyrazolyl-thiazole-coumarin hybrids: X-ray characterization, Hirshfeld surface analysis and DFT calculations
title Recurrent π-π stacking motifs in three new 4,5-dihydropyrazolyl-thiazole-coumarin hybrids: X-ray characterization, Hirshfeld surface analysis and DFT calculations
spellingShingle Recurrent π-π stacking motifs in three new 4,5-dihydropyrazolyl-thiazole-coumarin hybrids: X-ray characterization, Hirshfeld surface analysis and DFT calculations
Madni, Murtaza
COUMARIN
INTERMOLECULAR INTERACTIONS
DFT
HIRSHFELD SURFACES
title_short Recurrent π-π stacking motifs in three new 4,5-dihydropyrazolyl-thiazole-coumarin hybrids: X-ray characterization, Hirshfeld surface analysis and DFT calculations
title_full Recurrent π-π stacking motifs in three new 4,5-dihydropyrazolyl-thiazole-coumarin hybrids: X-ray characterization, Hirshfeld surface analysis and DFT calculations
title_fullStr Recurrent π-π stacking motifs in three new 4,5-dihydropyrazolyl-thiazole-coumarin hybrids: X-ray characterization, Hirshfeld surface analysis and DFT calculations
title_full_unstemmed Recurrent π-π stacking motifs in three new 4,5-dihydropyrazolyl-thiazole-coumarin hybrids: X-ray characterization, Hirshfeld surface analysis and DFT calculations
title_sort Recurrent π-π stacking motifs in three new 4,5-dihydropyrazolyl-thiazole-coumarin hybrids: X-ray characterization, Hirshfeld surface analysis and DFT calculations
dc.creator.none.fl_str_mv Madni, Murtaza
Ahmed, Muhammad Naeem
Hafeez, Muhammad
Ashfaq, Muhammad
Tahir, Muhammad Nawaz
Gil, Diego Mauricio
Galmés, Bartomeu
Hameed, Shahid
Frontera, Antonio
author Madni, Murtaza
author_facet Madni, Murtaza
Ahmed, Muhammad Naeem
Hafeez, Muhammad
Ashfaq, Muhammad
Tahir, Muhammad Nawaz
Gil, Diego Mauricio
Galmés, Bartomeu
Hameed, Shahid
Frontera, Antonio
author_role author
author2 Ahmed, Muhammad Naeem
Hafeez, Muhammad
Ashfaq, Muhammad
Tahir, Muhammad Nawaz
Gil, Diego Mauricio
Galmés, Bartomeu
Hameed, Shahid
Frontera, Antonio
author2_role author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv COUMARIN
INTERMOLECULAR INTERACTIONS
DFT
HIRSHFELD SURFACES
topic COUMARIN
INTERMOLECULAR INTERACTIONS
DFT
HIRSHFELD SURFACES
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 and X-ray characterization of three new 4,5-dihydropyrazolylthiazole-coumarin hybrids (1-3) are reported herein, namely 3-(2-(3,5-bis(4-chlorophenyl)-4,5-dihydropyrazol-1-yl)thiazol-4-yl)-2H-chromen-2-one (1), 3-(2-(5-(4-chlorophenyl)-4,5-dihydro-3-phenylpyrazol-1-yl)thiazol-4-yl)-2H-chromen-2-one (2) and 3-(2-(3-(4-chlorophenyl)-4,5-dihydro-5-p-tolylpyrazol-1-yl)thiazol-4-yl)-2H-chromen-2-one (3). A detailed structural analysis of the noncovalent interactions and their evaluation using Hirshfeld surface analysis is also reported, evidencing the importance of C-H⋯O and π-π interactions. Finally, DFT calculations along with the molecular electrostatic potential (MEP) and NCIplot index analysis have been used to evaluate those interactions energetically and to investigate the relative importance of two different π-stacking modes that are recurrent binding motifs in the solid state architecture of the three complexes.
Fil: Madni, Murtaza. Quaiad-i-Azam University; Pakistán
Fil: Ahmed, Muhammad Naeem. University of Azad Jammu and Kashmir; Pakistán
Fil: Hafeez, Muhammad. University of Azad Jammu and Kashmir; Pakistán
Fil: Ashfaq, Muhammad. University of Sargodha; Pakistán
Fil: Tahir, Muhammad Nawaz. University of Sargodha; Pakistán
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. Instituto de Química Orgánica; Argentina
Fil: Galmés, Bartomeu. Universidad de las Islas Baleares; España
Fil: Hameed, Shahid. Quaiad-i-Azam University; Pakistán
Fil: Frontera, Antonio. Universidad de las Islas Baleares; España
description The synthesis and X-ray characterization of three new 4,5-dihydropyrazolylthiazole-coumarin hybrids (1-3) are reported herein, namely 3-(2-(3,5-bis(4-chlorophenyl)-4,5-dihydropyrazol-1-yl)thiazol-4-yl)-2H-chromen-2-one (1), 3-(2-(5-(4-chlorophenyl)-4,5-dihydro-3-phenylpyrazol-1-yl)thiazol-4-yl)-2H-chromen-2-one (2) and 3-(2-(3-(4-chlorophenyl)-4,5-dihydro-5-p-tolylpyrazol-1-yl)thiazol-4-yl)-2H-chromen-2-one (3). A detailed structural analysis of the noncovalent interactions and their evaluation using Hirshfeld surface analysis is also reported, evidencing the importance of C-H⋯O and π-π interactions. Finally, DFT calculations along with the molecular electrostatic potential (MEP) and NCIplot index analysis have been used to evaluate those interactions energetically and to investigate the relative importance of two different π-stacking modes that are recurrent binding motifs in the solid state architecture of the three complexes.
publishDate 2020
dc.date.none.fl_str_mv 2020-09
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/11336/143346
Madni, Murtaza; Ahmed, Muhammad Naeem; Hafeez, Muhammad; Ashfaq, Muhammad; Tahir, Muhammad Nawaz; et al.; Recurrent π-π stacking motifs in three new 4,5-dihydropyrazolyl-thiazole-coumarin hybrids: X-ray characterization, Hirshfeld surface analysis and DFT calculations; Royal Society of Chemistry; New Journal of Chemistry; 44; 34; 9-2020; 14592-14603
1144-0546
1369-9261
CONICET Digital
CONICET
url http://hdl.handle.net/11336/143346
identifier_str_mv Madni, Murtaza; Ahmed, Muhammad Naeem; Hafeez, Muhammad; Ashfaq, Muhammad; Tahir, Muhammad Nawaz; et al.; Recurrent π-π stacking motifs in three new 4,5-dihydropyrazolyl-thiazole-coumarin hybrids: X-ray characterization, Hirshfeld surface analysis and DFT calculations; Royal Society of Chemistry; New Journal of Chemistry; 44; 34; 9-2020; 14592-14603
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/url/http://pubs.rsc.org/en/Content/ArticleLanding/2020/NJ/D0NJ02931A
info:eu-repo/semantics/altIdentifier/doi/10.1039/D0NJ02931A
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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score 13.22299

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