Intramolecular sp2-sp3 disequalization of chemically identical sulfonamide nitrogen atoms: single crystal X-Ray diffraction characterization, hirshfeld surface analysis and DFT cal...

Autores
Kletskov, Alexey V.; Gil, Diego Mauricio; Frontera, Antonio; Zaytsev, Vladimir P.; Merkulova, Natalia L.; Beltsova, Ksenia R.; Sinelshchikova, Anna A.; Grigoriev, Mikhail S.; Grudova, Mariya V.; Zubkov, Fedor I.
Año de publicación
2020
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
In this manuscript, the synthesis and single crystal X-ray diffraction characterization of four N-substituted 1,3,5-triazinanes are reported along with a detailed analysis of the noncovalent interactions observed in the solid state architecture to these compounds, focusing on C–H···π and C–H···O H-bonding interactions. These noncovalent contacts have been characterized energetically by using DFT calculations and also by Hirshfeld surface analysis. In addition, the supramolecular assemblies have been characterized using the quantum theory of “atoms-in-molecules” (QTAIM) and molecular electrostatic potential (MEP) calculations. The XRD analysis revealed a never before observed feature of the crystalline structure of some molecules: symmetrically substituted 1,3,5-triazacyclohexanes possess two chemically identical sulfonamide nitrogen atoms in different sp2 and sp3-hybridizations.
Fil: Kletskov, Alexey V.. University of Russia; 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
Fil: Frontera, Antonio. Universidad de las Islas Baleares; España
Fil: Zaytsev, Vladimir P.. University of Russia; Rusia
Fil: Merkulova, Natalia L.. University of Russia; Rusia
Fil: Beltsova, Ksenia R.. University of Russia; Rusia
Fil: Sinelshchikova, Anna A.. University of Russia; Rusia
Fil: Grigoriev, Mikhail S.. University of Russia; Rusia
Fil: Grudova, Mariya V.. University of Russia; Rusia
Fil: Zubkov, Fedor I.. University of Russia; Rusia
Materia
TRIAZINANE
1,3,5-TRIAZACYCLOHEXANE
HIRSHFELD SURFACE ANALYSIS
DFT STUDY
H-BONDING
SULFONAMIDES
HYBRIDIZATION OF A NITROGEN ATOM IN SULFONAMIDES
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:11336/143345
Acceder
id CONICETDig_402982013c3d15cbab82aca14b82d673
oai_identifier_str oai:ri.conicet.gov.ar:11336/143345
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Intramolecular sp2-sp3 disequalization of chemically identical sulfonamide nitrogen atoms: single crystal X-Ray diffraction characterization, hirshfeld surface analysis and DFT calculations of N-substituted hexahydro-1,3,5-triazinesKletskov, Alexey V.Gil, Diego MauricioFrontera, AntonioZaytsev, Vladimir P.Merkulova, Natalia L.Beltsova, Ksenia R.Sinelshchikova, Anna A.Grigoriev, Mikhail S.Grudova, Mariya V.Zubkov, Fedor I.TRIAZINANE1,3,5-TRIAZACYCLOHEXANEHIRSHFELD SURFACE ANALYSISDFT STUDYH-BONDINGSULFONAMIDESHYBRIDIZATION OF A NITROGEN ATOM IN SULFONAMIDEShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1In this manuscript, the synthesis and single crystal X-ray diffraction characterization of four N-substituted 1,3,5-triazinanes are reported along with a detailed analysis of the noncovalent interactions observed in the solid state architecture to these compounds, focusing on C–H···π and C–H···O H-bonding interactions. These noncovalent contacts have been characterized energetically by using DFT calculations and also by Hirshfeld surface analysis. In addition, the supramolecular assemblies have been characterized using the quantum theory of “atoms-in-molecules” (QTAIM) and molecular electrostatic potential (MEP) calculations. The XRD analysis revealed a never before observed feature of the crystalline structure of some molecules: symmetrically substituted 1,3,5-triazacyclohexanes possess two chemically identical sulfonamide nitrogen atoms in different sp2 and sp3-hybridizations.Fil: Kletskov, Alexey V.. University of Russia; 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; ArgentinaFil: Frontera, Antonio. Universidad de las Islas Baleares; EspañaFil: Zaytsev, Vladimir P.. University of Russia; RusiaFil: Merkulova, Natalia L.. University of Russia; RusiaFil: Beltsova, Ksenia R.. University of Russia; RusiaFil: Sinelshchikova, Anna A.. University of Russia; RusiaFil: Grigoriev, Mikhail S.. University of Russia; RusiaFil: Grudova, Mariya V.. University of Russia; RusiaFil: Zubkov, Fedor I.. University of Russia; RusiaMDPI2020-05info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/143345Kletskov, Alexey V.; Gil, Diego Mauricio; Frontera, Antonio; Zaytsev, Vladimir P.; Merkulova, Natalia L.; et al.; Intramolecular sp2-sp3 disequalization of chemically identical sulfonamide nitrogen atoms: single crystal X-Ray diffraction characterization, hirshfeld surface analysis and DFT calculations of N-substituted hexahydro-1,3,5-triazines; MDPI; Crystals; 10; 5; 5-2020; 1-14; 3692073-43522073-4352CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.3390/cryst10050369info:eu-repo/semantics/altIdentifier/url/https://www.mdpi.com/2073-4352/10/5/369info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:00:04Zoai:ri.conicet.gov.ar:11336/143345instacron: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 10:00:04.38CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Intramolecular sp2-sp3 disequalization of chemically identical sulfonamide nitrogen atoms: single crystal X-Ray diffraction characterization, hirshfeld surface analysis and DFT calculations of N-substituted hexahydro-1,3,5-triazines
title Intramolecular sp2-sp3 disequalization of chemically identical sulfonamide nitrogen atoms: single crystal X-Ray diffraction characterization, hirshfeld surface analysis and DFT calculations of N-substituted hexahydro-1,3,5-triazines
spellingShingle Intramolecular sp2-sp3 disequalization of chemically identical sulfonamide nitrogen atoms: single crystal X-Ray diffraction characterization, hirshfeld surface analysis and DFT calculations of N-substituted hexahydro-1,3,5-triazines
Kletskov, Alexey V.
TRIAZINANE
1,3,5-TRIAZACYCLOHEXANE
HIRSHFELD SURFACE ANALYSIS
DFT STUDY
H-BONDING
SULFONAMIDES
HYBRIDIZATION OF A NITROGEN ATOM IN SULFONAMIDES
title_short Intramolecular sp2-sp3 disequalization of chemically identical sulfonamide nitrogen atoms: single crystal X-Ray diffraction characterization, hirshfeld surface analysis and DFT calculations of N-substituted hexahydro-1,3,5-triazines
title_full Intramolecular sp2-sp3 disequalization of chemically identical sulfonamide nitrogen atoms: single crystal X-Ray diffraction characterization, hirshfeld surface analysis and DFT calculations of N-substituted hexahydro-1,3,5-triazines
title_fullStr Intramolecular sp2-sp3 disequalization of chemically identical sulfonamide nitrogen atoms: single crystal X-Ray diffraction characterization, hirshfeld surface analysis and DFT calculations of N-substituted hexahydro-1,3,5-triazines
title_full_unstemmed Intramolecular sp2-sp3 disequalization of chemically identical sulfonamide nitrogen atoms: single crystal X-Ray diffraction characterization, hirshfeld surface analysis and DFT calculations of N-substituted hexahydro-1,3,5-triazines
title_sort Intramolecular sp2-sp3 disequalization of chemically identical sulfonamide nitrogen atoms: single crystal X-Ray diffraction characterization, hirshfeld surface analysis and DFT calculations of N-substituted hexahydro-1,3,5-triazines
dc.creator.none.fl_str_mv Kletskov, Alexey V.
Gil, Diego Mauricio
Frontera, Antonio
Zaytsev, Vladimir P.
Merkulova, Natalia L.
Beltsova, Ksenia R.
Sinelshchikova, Anna A.
Grigoriev, Mikhail S.
Grudova, Mariya V.
Zubkov, Fedor I.
author Kletskov, Alexey V.
author_facet Kletskov, Alexey V.
Gil, Diego Mauricio
Frontera, Antonio
Zaytsev, Vladimir P.
Merkulova, Natalia L.
Beltsova, Ksenia R.
Sinelshchikova, Anna A.
Grigoriev, Mikhail S.
Grudova, Mariya V.
Zubkov, Fedor I.
author_role author
author2 Gil, Diego Mauricio
Frontera, Antonio
Zaytsev, Vladimir P.
Merkulova, Natalia L.
Beltsova, Ksenia R.
Sinelshchikova, Anna A.
Grigoriev, Mikhail S.
Grudova, Mariya V.
Zubkov, Fedor I.
author2_role author
author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv TRIAZINANE
1,3,5-TRIAZACYCLOHEXANE
HIRSHFELD SURFACE ANALYSIS
DFT STUDY
H-BONDING
SULFONAMIDES
HYBRIDIZATION OF A NITROGEN ATOM IN SULFONAMIDES
topic TRIAZINANE
1,3,5-TRIAZACYCLOHEXANE
HIRSHFELD SURFACE ANALYSIS
DFT STUDY
H-BONDING
SULFONAMIDES
HYBRIDIZATION OF A NITROGEN ATOM IN SULFONAMIDES
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv In this manuscript, the synthesis and single crystal X-ray diffraction characterization of four N-substituted 1,3,5-triazinanes are reported along with a detailed analysis of the noncovalent interactions observed in the solid state architecture to these compounds, focusing on C–H···π and C–H···O H-bonding interactions. These noncovalent contacts have been characterized energetically by using DFT calculations and also by Hirshfeld surface analysis. In addition, the supramolecular assemblies have been characterized using the quantum theory of “atoms-in-molecules” (QTAIM) and molecular electrostatic potential (MEP) calculations. The XRD analysis revealed a never before observed feature of the crystalline structure of some molecules: symmetrically substituted 1,3,5-triazacyclohexanes possess two chemically identical sulfonamide nitrogen atoms in different sp2 and sp3-hybridizations.
Fil: Kletskov, Alexey V.. University of Russia; 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
Fil: Frontera, Antonio. Universidad de las Islas Baleares; España
Fil: Zaytsev, Vladimir P.. University of Russia; Rusia
Fil: Merkulova, Natalia L.. University of Russia; Rusia
Fil: Beltsova, Ksenia R.. University of Russia; Rusia
Fil: Sinelshchikova, Anna A.. University of Russia; Rusia
Fil: Grigoriev, Mikhail S.. University of Russia; Rusia
Fil: Grudova, Mariya V.. University of Russia; Rusia
Fil: Zubkov, Fedor I.. University of Russia; Rusia
description In this manuscript, the synthesis and single crystal X-ray diffraction characterization of four N-substituted 1,3,5-triazinanes are reported along with a detailed analysis of the noncovalent interactions observed in the solid state architecture to these compounds, focusing on C–H···π and C–H···O H-bonding interactions. These noncovalent contacts have been characterized energetically by using DFT calculations and also by Hirshfeld surface analysis. In addition, the supramolecular assemblies have been characterized using the quantum theory of “atoms-in-molecules” (QTAIM) and molecular electrostatic potential (MEP) calculations. The XRD analysis revealed a never before observed feature of the crystalline structure of some molecules: symmetrically substituted 1,3,5-triazacyclohexanes possess two chemically identical sulfonamide nitrogen atoms in different sp2 and sp3-hybridizations.
publishDate 2020
dc.date.none.fl_str_mv 2020-05
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/11336/143345
Kletskov, Alexey V.; Gil, Diego Mauricio; Frontera, Antonio; Zaytsev, Vladimir P.; Merkulova, Natalia L.; et al.; Intramolecular sp2-sp3 disequalization of chemically identical sulfonamide nitrogen atoms: single crystal X-Ray diffraction characterization, hirshfeld surface analysis and DFT calculations of N-substituted hexahydro-1,3,5-triazines; MDPI; Crystals; 10; 5; 5-2020; 1-14; 369
2073-4352
2073-4352
CONICET Digital
CONICET
url http://hdl.handle.net/11336/143345
identifier_str_mv Kletskov, Alexey V.; Gil, Diego Mauricio; Frontera, Antonio; Zaytsev, Vladimir P.; Merkulova, Natalia L.; et al.; Intramolecular sp2-sp3 disequalization of chemically identical sulfonamide nitrogen atoms: single crystal X-Ray diffraction characterization, hirshfeld surface analysis and DFT calculations of N-substituted hexahydro-1,3,5-triazines; MDPI; Crystals; 10; 5; 5-2020; 1-14; 369
2073-4352
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.3390/cryst10050369
info:eu-repo/semantics/altIdentifier/url/https://www.mdpi.com/2073-4352/10/5/369
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
dc.publisher.none.fl_str_mv MDPI
publisher.none.fl_str_mv MDPI
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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