Synthesis and X-ray characterization of two new 1,4-benzoxazine derivatives: Structural analysis and DFT calculations

Autores
Bashir, Muhammad Adnan; Ahmed, Muhammad Naeem; Gil, Diego Mauricio; Frontera, Antonio; Sun, Jianguo; Almutairi, Tahani Mazyad; Tahir, Muhammad N.; Ibrahim, Mahmoud A. A.
Año de publicación
2024
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The synthesis and XRD characterization of two new 1,4-benzoxazine derivatives (3a-5a) namely ethyl‐6‐nitro‐3a‐(p‐tolylamino)‐1,2,3,3a‐tetrahydrobenzo[b]cyclopenta[e][1,4]oxa-zine‐9a(9H)‐carboxylate (3a) and methyl-6,10b-dimethyl-5a,6,10b,11-tetrahydrobenzo[5,6][1,4]oxazino[2,3-b]indole-2-carboxylate (5a) are reported herein. In both compounds it is observed the formation of π···π and CH···π interactions and strong NH···O H-bonds, which were studied energetically at the PBE0-D3/def2-TZVP level of theory. The Hisrhfeld surface and QTAIM analyses and NCI plots were used to study the nature and the extent of different intermolecular interactions observed in both structures, revealing the existence of additional and synthons. In addition, using the potential energy density as energy predictor, the QTAIM method is useful to investigate the relative contribution of each interaction to the formation of the assemblies.
Fil: Bashir, Muhammad Adnan. Peking University; China
Fil: Ahmed, Muhammad Naeem. University Of Azad Jammu And Kashmir; 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
Fil: Frontera, Antonio. Universidad de las Islas Baleares; España
Fil: Sun, Jianguo. Peking University; China
Fil: Almutairi, Tahani Mazyad. King Saud University; Arabia Saudita
Fil: Tahir, Muhammad N.. University Of Sargodha; Pakistán
Fil: Ibrahim, Mahmoud A. A.. Minia University; Egipto
Materia
1,4-BENZOXAZINE
[4+2] CYCLOADDITION
BIOMIMETIC OXIDATION
DFT CALCULATIONS
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:11336/262527
Acceder
id CONICETDig_002621ae1e0021fd344ce48a5dc90e84
oai_identifier_str oai:ri.conicet.gov.ar:11336/262527
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis and X-ray characterization of two new 1,4-benzoxazine derivatives: Structural analysis and DFT calculationsBashir, Muhammad AdnanAhmed, Muhammad NaeemGil, Diego MauricioFrontera, AntonioSun, JianguoAlmutairi, Tahani MazyadTahir, Muhammad N.Ibrahim, Mahmoud A. A.1,4-BENZOXAZINE[4+2] CYCLOADDITIONBIOMIMETIC OXIDATIONDFT CALCULATIONShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The synthesis and XRD characterization of two new 1,4-benzoxazine derivatives (3a-5a) namely ethyl‐6‐nitro‐3a‐(p‐tolylamino)‐1,2,3,3a‐tetrahydrobenzo[b]cyclopenta[e][1,4]oxa-zine‐9a(9H)‐carboxylate (3a) and methyl-6,10b-dimethyl-5a,6,10b,11-tetrahydrobenzo[5,6][1,4]oxazino[2,3-b]indole-2-carboxylate (5a) are reported herein. In both compounds it is observed the formation of π···π and CH···π interactions and strong NH···O H-bonds, which were studied energetically at the PBE0-D3/def2-TZVP level of theory. The Hisrhfeld surface and QTAIM analyses and NCI plots were used to study the nature and the extent of different intermolecular interactions observed in both structures, revealing the existence of additional and synthons. In addition, using the potential energy density as energy predictor, the QTAIM method is useful to investigate the relative contribution of each interaction to the formation of the assemblies.Fil: Bashir, Muhammad Adnan. Peking University; ChinaFil: Ahmed, Muhammad Naeem. University Of Azad Jammu And Kashmir; 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; ArgentinaFil: Frontera, Antonio. Universidad de las Islas Baleares; EspañaFil: Sun, Jianguo. Peking University; ChinaFil: Almutairi, Tahani Mazyad. King Saud University; Arabia SauditaFil: Tahir, Muhammad N.. University Of Sargodha; PakistánFil: Ibrahim, Mahmoud A. A.. Minia University; EgiptoElsevier Science2024-11info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/262527Bashir, Muhammad Adnan; Ahmed, Muhammad Naeem; Gil, Diego Mauricio; Frontera, Antonio; Sun, Jianguo; et al.; Synthesis and X-ray characterization of two new 1,4-benzoxazine derivatives: Structural analysis and DFT calculations; Elsevier Science; Journal of Molecular Structure; 1315; 11-2024; 1-120022-2860CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.molstruc.2024.138802info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-12-23T13:13:19Zoai:ri.conicet.gov.ar:11336/262527instacron: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:34982025-12-23 13:13:19.96CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis and X-ray characterization of two new 1,4-benzoxazine derivatives: Structural analysis and DFT calculations
title Synthesis and X-ray characterization of two new 1,4-benzoxazine derivatives: Structural analysis and DFT calculations
spellingShingle Synthesis and X-ray characterization of two new 1,4-benzoxazine derivatives: Structural analysis and DFT calculations
Bashir, Muhammad Adnan
1,4-BENZOXAZINE
[4+2] CYCLOADDITION
BIOMIMETIC OXIDATION
DFT CALCULATIONS
title_short Synthesis and X-ray characterization of two new 1,4-benzoxazine derivatives: Structural analysis and DFT calculations
title_full Synthesis and X-ray characterization of two new 1,4-benzoxazine derivatives: Structural analysis and DFT calculations
title_fullStr Synthesis and X-ray characterization of two new 1,4-benzoxazine derivatives: Structural analysis and DFT calculations
title_full_unstemmed Synthesis and X-ray characterization of two new 1,4-benzoxazine derivatives: Structural analysis and DFT calculations
title_sort Synthesis and X-ray characterization of two new 1,4-benzoxazine derivatives: Structural analysis and DFT calculations
dc.creator.none.fl_str_mv Bashir, Muhammad Adnan
Ahmed, Muhammad Naeem
Gil, Diego Mauricio
Frontera, Antonio
Sun, Jianguo
Almutairi, Tahani Mazyad
Tahir, Muhammad N.
Ibrahim, Mahmoud A. A.
author Bashir, Muhammad Adnan
author_facet Bashir, Muhammad Adnan
Ahmed, Muhammad Naeem
Gil, Diego Mauricio
Frontera, Antonio
Sun, Jianguo
Almutairi, Tahani Mazyad
Tahir, Muhammad N.
Ibrahim, Mahmoud A. A.
author_role author
author2 Ahmed, Muhammad Naeem
Gil, Diego Mauricio
Frontera, Antonio
Sun, Jianguo
Almutairi, Tahani Mazyad
Tahir, Muhammad N.
Ibrahim, Mahmoud A. A.
author2_role author
author
author
author
author
author
author
dc.subject.none.fl_str_mv 1,4-BENZOXAZINE
[4+2] CYCLOADDITION
BIOMIMETIC OXIDATION
DFT CALCULATIONS
topic 1,4-BENZOXAZINE
[4+2] CYCLOADDITION
BIOMIMETIC OXIDATION
DFT CALCULATIONS
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 XRD characterization of two new 1,4-benzoxazine derivatives (3a-5a) namely ethyl‐6‐nitro‐3a‐(p‐tolylamino)‐1,2,3,3a‐tetrahydrobenzo[b]cyclopenta[e][1,4]oxa-zine‐9a(9H)‐carboxylate (3a) and methyl-6,10b-dimethyl-5a,6,10b,11-tetrahydrobenzo[5,6][1,4]oxazino[2,3-b]indole-2-carboxylate (5a) are reported herein. In both compounds it is observed the formation of π···π and CH···π interactions and strong NH···O H-bonds, which were studied energetically at the PBE0-D3/def2-TZVP level of theory. The Hisrhfeld surface and QTAIM analyses and NCI plots were used to study the nature and the extent of different intermolecular interactions observed in both structures, revealing the existence of additional and synthons. In addition, using the potential energy density as energy predictor, the QTAIM method is useful to investigate the relative contribution of each interaction to the formation of the assemblies.
Fil: Bashir, Muhammad Adnan. Peking University; China
Fil: Ahmed, Muhammad Naeem. University Of Azad Jammu And Kashmir; 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
Fil: Frontera, Antonio. Universidad de las Islas Baleares; España
Fil: Sun, Jianguo. Peking University; China
Fil: Almutairi, Tahani Mazyad. King Saud University; Arabia Saudita
Fil: Tahir, Muhammad N.. University Of Sargodha; Pakistán
Fil: Ibrahim, Mahmoud A. A.. Minia University; Egipto
description The synthesis and XRD characterization of two new 1,4-benzoxazine derivatives (3a-5a) namely ethyl‐6‐nitro‐3a‐(p‐tolylamino)‐1,2,3,3a‐tetrahydrobenzo[b]cyclopenta[e][1,4]oxa-zine‐9a(9H)‐carboxylate (3a) and methyl-6,10b-dimethyl-5a,6,10b,11-tetrahydrobenzo[5,6][1,4]oxazino[2,3-b]indole-2-carboxylate (5a) are reported herein. In both compounds it is observed the formation of π···π and CH···π interactions and strong NH···O H-bonds, which were studied energetically at the PBE0-D3/def2-TZVP level of theory. The Hisrhfeld surface and QTAIM analyses and NCI plots were used to study the nature and the extent of different intermolecular interactions observed in both structures, revealing the existence of additional and synthons. In addition, using the potential energy density as energy predictor, the QTAIM method is useful to investigate the relative contribution of each interaction to the formation of the assemblies.
publishDate 2024
dc.date.none.fl_str_mv 2024-11
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/11336/262527
Bashir, Muhammad Adnan; Ahmed, Muhammad Naeem; Gil, Diego Mauricio; Frontera, Antonio; Sun, Jianguo; et al.; Synthesis and X-ray characterization of two new 1,4-benzoxazine derivatives: Structural analysis and DFT calculations; Elsevier Science; Journal of Molecular Structure; 1315; 11-2024; 1-12
0022-2860
CONICET Digital
CONICET
url http://hdl.handle.net/11336/262527
identifier_str_mv Bashir, Muhammad Adnan; Ahmed, Muhammad Naeem; Gil, Diego Mauricio; Frontera, Antonio; Sun, Jianguo; et al.; Synthesis and X-ray characterization of two new 1,4-benzoxazine derivatives: Structural analysis and DFT calculations; Elsevier Science; Journal of Molecular Structure; 1315; 11-2024; 1-12
0022-2860
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.2024.138802
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
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 12.441415

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