Synthesis, X-ray characterization and theoretical study of 3 a ,6:7,9 a-diepoxybenzo [de] isoquinoline derivatives: on the importance of F⋯O interactions

Autores
Grudova, Mariya V.; Gil, Diego Mauricio; Khrustalev, Victor N.; Nikitina, Eugeniya V.; Sinelshchikova, Anna A.; Grigoriev, Mikhail S.; Kletskov, Alexey V.; Frontera, Antonio; Zubkov, Fedor I.
Año de publicación
2020
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The synthesis, X-ray characterization and Hirshfeld surface analysis of a series of tetrahydrodiepoxybenzo[de]isoquinoline derivatives obtained by the tandem [4+2] cycloaddition between perfluorobut-2-yne dienophile (F3C–C≡C–CF3) and a row of N,N-bis(furan-2-ylmethyl)-4-Rbenzenesulfonamides (bis-dienes, R = Me, F, Cl, Br, I) are reported in this manuscript. The implementation of kinetic/thermodynamic control allowed to obtain both “pincer”- and “domino”-types adducts in good/moderate yields. In the solid state, most of the pincer adducts form self-assembled dimers (R = Me, Cl, Br, I) and, contrariwise, the domino adducts form 1D supramolecular chains, which are described in detail herein. Remarkably, in the self-assembled dimers, bifurcated halogen bonds involving one fluorine atom of the CF3 group and both O-atoms of sulfonamide are formed, which have been analyzed using DFT calculations, QTAIM and NCIplot computational tools.
Fil: Grudova, Mariya V.. Peoples’ Friendship University; Rusia
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: Khrustalev, Victor N.. Peoples’ Friendship University; Rusia. Institute of Organic Chemistry ND. Zelinsky; Rusia
Fil: Nikitina, Eugeniya V.. Peoples’ Friendship University; Rusia
Fil: Sinelshchikova, Anna A.. Academy of Sciences. Frumkin Institute of Physical Chemistry and Electrochemistry; Rusia
Fil: Grigoriev, Mikhail S.. Academy of Sciences. Frumkin Institute of Physical Chemistry and Electrochemistry; Rusia
Fil: Kletskov, Alexey V.. Peoples’ Friendship University; Rusia
Fil: Frontera, Antonio. Universidad de las Islas Baleares; España
Fil: Zubkov, Fedor I.. Peoples’ Friendship University; Rusia
Materia
F···O INTERACTIONS
X-RAY STRUCTURE
HIRSHFELD SURFACES
DFT CALCULATIONS
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:11336/143349
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/143349
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis, X-ray characterization and theoretical study of 3 a ,6:7,9 a-diepoxybenzo [de] isoquinoline derivatives: on the importance of F⋯O interactionsGrudova, Mariya V.Gil, Diego MauricioKhrustalev, Victor N.Nikitina, Eugeniya V.Sinelshchikova, Anna A.Grigoriev, Mikhail S.Kletskov, Alexey V.Frontera, AntonioZubkov, Fedor I.F···O INTERACTIONSX-RAY STRUCTUREHIRSHFELD SURFACESDFT CALCULATIONShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The synthesis, X-ray characterization and Hirshfeld surface analysis of a series of tetrahydrodiepoxybenzo[de]isoquinoline derivatives obtained by the tandem [4+2] cycloaddition between perfluorobut-2-yne dienophile (F3C–C≡C–CF3) and a row of N,N-bis(furan-2-ylmethyl)-4-Rbenzenesulfonamides (bis-dienes, R = Me, F, Cl, Br, I) are reported in this manuscript. The implementation of kinetic/thermodynamic control allowed to obtain both “pincer”- and “domino”-types adducts in good/moderate yields. In the solid state, most of the pincer adducts form self-assembled dimers (R = Me, Cl, Br, I) and, contrariwise, the domino adducts form 1D supramolecular chains, which are described in detail herein. Remarkably, in the self-assembled dimers, bifurcated halogen bonds involving one fluorine atom of the CF3 group and both O-atoms of sulfonamide are formed, which have been analyzed using DFT calculations, QTAIM and NCIplot computational tools.Fil: Grudova, Mariya V.. Peoples’ Friendship University; RusiaFil: 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: Khrustalev, Victor N.. Peoples’ Friendship University; Rusia. Institute of Organic Chemistry ND. Zelinsky; RusiaFil: Nikitina, Eugeniya V.. Peoples’ Friendship University; RusiaFil: Sinelshchikova, Anna A.. Academy of Sciences. Frumkin Institute of Physical Chemistry and Electrochemistry; RusiaFil: Grigoriev, Mikhail S.. Academy of Sciences. Frumkin Institute of Physical Chemistry and Electrochemistry; RusiaFil: Kletskov, Alexey V.. Peoples’ Friendship University; RusiaFil: Frontera, Antonio. Universidad de las Islas Baleares; EspañaFil: Zubkov, Fedor I.. Peoples’ Friendship University; RusiaRoyal Society of Chemistry2020-12-27info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/143349Grudova, Mariya V.; Gil, Diego Mauricio; Khrustalev, Victor N.; Nikitina, Eugeniya V.; Sinelshchikova, Anna A.; et al.; Synthesis, X-ray characterization and theoretical study of 3 a ,6:7,9 a-diepoxybenzo [de] isoquinoline derivatives: on the importance of F⋯O interactions; Royal Society of Chemistry; New Journal of Chemistry; 44; 46; 27-12-2020; 20167-201801144-05461369-9261CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1039/D0NJ04328Ainfo:eu-repo/semantics/altIdentifier/url/https://pubs.rsc.org/en/content/articlelanding/2020/nj/d0nj04328ainfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:39:17Zoai:ri.conicet.gov.ar:11336/143349instacron: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 10:39:17.706CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis, X-ray characterization and theoretical study of 3 a ,6:7,9 a-diepoxybenzo [de] isoquinoline derivatives: on the importance of F⋯O interactions
title Synthesis, X-ray characterization and theoretical study of 3 a ,6:7,9 a-diepoxybenzo [de] isoquinoline derivatives: on the importance of F⋯O interactions
spellingShingle Synthesis, X-ray characterization and theoretical study of 3 a ,6:7,9 a-diepoxybenzo [de] isoquinoline derivatives: on the importance of F⋯O interactions
Grudova, Mariya V.
F···O INTERACTIONS
X-RAY STRUCTURE
HIRSHFELD SURFACES
DFT CALCULATIONS
title_short Synthesis, X-ray characterization and theoretical study of 3 a ,6:7,9 a-diepoxybenzo [de] isoquinoline derivatives: on the importance of F⋯O interactions
title_full Synthesis, X-ray characterization and theoretical study of 3 a ,6:7,9 a-diepoxybenzo [de] isoquinoline derivatives: on the importance of F⋯O interactions
title_fullStr Synthesis, X-ray characterization and theoretical study of 3 a ,6:7,9 a-diepoxybenzo [de] isoquinoline derivatives: on the importance of F⋯O interactions
title_full_unstemmed Synthesis, X-ray characterization and theoretical study of 3 a ,6:7,9 a-diepoxybenzo [de] isoquinoline derivatives: on the importance of F⋯O interactions
title_sort Synthesis, X-ray characterization and theoretical study of 3 a ,6:7,9 a-diepoxybenzo [de] isoquinoline derivatives: on the importance of F⋯O interactions
dc.creator.none.fl_str_mv Grudova, Mariya V.
Gil, Diego Mauricio
Khrustalev, Victor N.
Nikitina, Eugeniya V.
Sinelshchikova, Anna A.
Grigoriev, Mikhail S.
Kletskov, Alexey V.
Frontera, Antonio
Zubkov, Fedor I.
author Grudova, Mariya V.
author_facet Grudova, Mariya V.
Gil, Diego Mauricio
Khrustalev, Victor N.
Nikitina, Eugeniya V.
Sinelshchikova, Anna A.
Grigoriev, Mikhail S.
Kletskov, Alexey V.
Frontera, Antonio
Zubkov, Fedor I.
author_role author
author2 Gil, Diego Mauricio
Khrustalev, Victor N.
Nikitina, Eugeniya V.
Sinelshchikova, Anna A.
Grigoriev, Mikhail S.
Kletskov, Alexey V.
Frontera, Antonio
Zubkov, Fedor I.
author2_role author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv F···O INTERACTIONS
X-RAY STRUCTURE
HIRSHFELD SURFACES
DFT CALCULATIONS
topic F···O INTERACTIONS
X-RAY STRUCTURE
HIRSHFELD SURFACES
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, X-ray characterization and Hirshfeld surface analysis of a series of tetrahydrodiepoxybenzo[de]isoquinoline derivatives obtained by the tandem [4+2] cycloaddition between perfluorobut-2-yne dienophile (F3C–C≡C–CF3) and a row of N,N-bis(furan-2-ylmethyl)-4-Rbenzenesulfonamides (bis-dienes, R = Me, F, Cl, Br, I) are reported in this manuscript. The implementation of kinetic/thermodynamic control allowed to obtain both “pincer”- and “domino”-types adducts in good/moderate yields. In the solid state, most of the pincer adducts form self-assembled dimers (R = Me, Cl, Br, I) and, contrariwise, the domino adducts form 1D supramolecular chains, which are described in detail herein. Remarkably, in the self-assembled dimers, bifurcated halogen bonds involving one fluorine atom of the CF3 group and both O-atoms of sulfonamide are formed, which have been analyzed using DFT calculations, QTAIM and NCIplot computational tools.
Fil: Grudova, Mariya V.. Peoples’ Friendship University; Rusia
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: Khrustalev, Victor N.. Peoples’ Friendship University; Rusia. Institute of Organic Chemistry ND. Zelinsky; Rusia
Fil: Nikitina, Eugeniya V.. Peoples’ Friendship University; Rusia
Fil: Sinelshchikova, Anna A.. Academy of Sciences. Frumkin Institute of Physical Chemistry and Electrochemistry; Rusia
Fil: Grigoriev, Mikhail S.. Academy of Sciences. Frumkin Institute of Physical Chemistry and Electrochemistry; Rusia
Fil: Kletskov, Alexey V.. Peoples’ Friendship University; Rusia
Fil: Frontera, Antonio. Universidad de las Islas Baleares; España
Fil: Zubkov, Fedor I.. Peoples’ Friendship University; Rusia
description The synthesis, X-ray characterization and Hirshfeld surface analysis of a series of tetrahydrodiepoxybenzo[de]isoquinoline derivatives obtained by the tandem [4+2] cycloaddition between perfluorobut-2-yne dienophile (F3C–C≡C–CF3) and a row of N,N-bis(furan-2-ylmethyl)-4-Rbenzenesulfonamides (bis-dienes, R = Me, F, Cl, Br, I) are reported in this manuscript. The implementation of kinetic/thermodynamic control allowed to obtain both “pincer”- and “domino”-types adducts in good/moderate yields. In the solid state, most of the pincer adducts form self-assembled dimers (R = Me, Cl, Br, I) and, contrariwise, the domino adducts form 1D supramolecular chains, which are described in detail herein. Remarkably, in the self-assembled dimers, bifurcated halogen bonds involving one fluorine atom of the CF3 group and both O-atoms of sulfonamide are formed, which have been analyzed using DFT calculations, QTAIM and NCIplot computational tools.
publishDate 2020
dc.date.none.fl_str_mv 2020-12-27
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/11336/143349
Grudova, Mariya V.; Gil, Diego Mauricio; Khrustalev, Victor N.; Nikitina, Eugeniya V.; Sinelshchikova, Anna A.; et al.; Synthesis, X-ray characterization and theoretical study of 3 a ,6:7,9 a-diepoxybenzo [de] isoquinoline derivatives: on the importance of F⋯O interactions; Royal Society of Chemistry; New Journal of Chemistry; 44; 46; 27-12-2020; 20167-20180
1144-0546
1369-9261
CONICET Digital
CONICET
url http://hdl.handle.net/11336/143349
identifier_str_mv Grudova, Mariya V.; Gil, Diego Mauricio; Khrustalev, Victor N.; Nikitina, Eugeniya V.; Sinelshchikova, Anna A.; et al.; Synthesis, X-ray characterization and theoretical study of 3 a ,6:7,9 a-diepoxybenzo [de] isoquinoline derivatives: on the importance of F⋯O interactions; Royal Society of Chemistry; New Journal of Chemistry; 44; 46; 27-12-2020; 20167-20180
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/D0NJ04328A
info:eu-repo/semantics/altIdentifier/url/https://pubs.rsc.org/en/content/articlelanding/2020/nj/d0nj04328a
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 13.070432

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