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
.jpg) 
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/143349
Ver los metadatos del registro completo
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| 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 Técnicas2025-10-22T12:11:33Zoai: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:34982025-10-22 12:11:33.53CONICET 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 | 
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| dc.publisher.none.fl_str_mv | Royal Society of Chemistry | 
| publisher.none.fl_str_mv | Royal Society of Chemistry | 
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