Raise the anchor! Synthesis, X-ray and NMR characterization of 1,3,5-triazinanes with an axial tert-butyl group

Autores
Kletskov, Alexey V.; Zatykina, Anastasya D.; Grudova, Mariya V.; Sinelshchikova, Anna A.; Grigoriev, Mikhail; Zaytsev, Vladimir P.; Gil, Diego Mauricio; Novikov, Roman A.; Zubkov, Fedor Ivanovich; Frontera, Antonio
Año de publicación
2020
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
N-t-Bu-N’,N’’-disulfonamide-1,3,5-triazinanes were synthesized and characterized by X-ray single crystal structure analysis. In the course of the X-ray structure elucidation, the first solid experimental evidence of the axial position of the tert-butyl group in unconstrained hexahydro-1,3,5-triazacyclohexanes was obtained. Dynamic low-temperature NMR analysis allowed to fully investigate a rare case of crystallization-driven unanchoring of the tert-butyl group in the chair conformation of saturated sixmembered cycles. DFT calculations show that the use of explicit solvent molecules is necessary to explain the equatorial position of the t-Bu group in solution. Otherwise, the axial conformer is the thermodynamically stable isomer.
Fil: Kletskov, Alexey V.. University of Russia; Rusia
Fil: Zatykina, Anastasya D.. University of Russia; Rusia
Fil: Grudova, Mariya V.. University of Russia; Rusia
Fil: Sinelshchikova, Anna A.. Academy of Sciences; Rusia
Fil: Grigoriev, Mikhail. Academy of Sciences; Rusia
Fil: Zaytsev, Vladimir P.. 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. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica; Argentina
Fil: Novikov, Roman A.. Academy of Sciences; Rusia
Fil: Zubkov, Fedor Ivanovich. University of Russia; Rusia
Fil: Frontera, Antonio. Universidad de las Islas Baleares; España
Materia
1,3,5-TRIAZINANES
SULFONAMIDES
NMR ANALYSIS
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:11336/143341
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/143341
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Raise the anchor! Synthesis, X-ray and NMR characterization of 1,3,5-triazinanes with an axial tert-butyl groupKletskov, Alexey V.Zatykina, Anastasya D.Grudova, Mariya V.Sinelshchikova, Anna A.Grigoriev, MikhailZaytsev, Vladimir P.Gil, Diego MauricioNovikov, Roman A.Zubkov, Fedor IvanovichFrontera, Antonio1,3,5-TRIAZINANESSULFONAMIDESNMR ANALYSISDFT CALCULATIONShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1N-t-Bu-N’,N’’-disulfonamide-1,3,5-triazinanes were synthesized and characterized by X-ray single crystal structure analysis. In the course of the X-ray structure elucidation, the first solid experimental evidence of the axial position of the tert-butyl group in unconstrained hexahydro-1,3,5-triazacyclohexanes was obtained. Dynamic low-temperature NMR analysis allowed to fully investigate a rare case of crystallization-driven unanchoring of the tert-butyl group in the chair conformation of saturated sixmembered cycles. DFT calculations show that the use of explicit solvent molecules is necessary to explain the equatorial position of the t-Bu group in solution. Otherwise, the axial conformer is the thermodynamically stable isomer.Fil: Kletskov, Alexey V.. University of Russia; RusiaFil: Zatykina, Anastasya D.. University of Russia; RusiaFil: Grudova, Mariya V.. University of Russia; RusiaFil: Sinelshchikova, Anna A.. Academy of Sciences; RusiaFil: Grigoriev, Mikhail. Academy of Sciences; RusiaFil: Zaytsev, Vladimir P.. 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; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica; ArgentinaFil: Novikov, Roman A.. Academy of Sciences; RusiaFil: Zubkov, Fedor Ivanovich. University of Russia; RusiaFil: Frontera, Antonio. Universidad de las Islas Baleares; EspañaRoyal Society of Chemistry2020-11info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/143341Kletskov, Alexey V.; Zatykina, Anastasya D.; Grudova, Mariya V.; Sinelshchikova, Anna A.; Grigoriev, Mikhail; et al.; Raise the anchor! Synthesis, X-ray and NMR characterization of 1,3,5-triazinanes with an axial tert-butyl group; Royal Society of Chemistry; Organic & Biomolecular Chemistry; 18; 41; 11-2020; 8386-83941477-05201477-0539CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1039/D0OB01201Ginfo:eu-repo/semantics/altIdentifier/url/https://pubs.rsc.org/en/content/articlelanding/2020/OB/D0OB01201Ginfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-22T11:47:30Zoai:ri.conicet.gov.ar:11336/143341instacron: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 11:47:31.11CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Raise the anchor! Synthesis, X-ray and NMR characterization of 1,3,5-triazinanes with an axial tert-butyl group
title Raise the anchor! Synthesis, X-ray and NMR characterization of 1,3,5-triazinanes with an axial tert-butyl group
spellingShingle Raise the anchor! Synthesis, X-ray and NMR characterization of 1,3,5-triazinanes with an axial tert-butyl group
Kletskov, Alexey V.
1,3,5-TRIAZINANES
SULFONAMIDES
NMR ANALYSIS
DFT CALCULATIONS
title_short Raise the anchor! Synthesis, X-ray and NMR characterization of 1,3,5-triazinanes with an axial tert-butyl group
title_full Raise the anchor! Synthesis, X-ray and NMR characterization of 1,3,5-triazinanes with an axial tert-butyl group
title_fullStr Raise the anchor! Synthesis, X-ray and NMR characterization of 1,3,5-triazinanes with an axial tert-butyl group
title_full_unstemmed Raise the anchor! Synthesis, X-ray and NMR characterization of 1,3,5-triazinanes with an axial tert-butyl group
title_sort Raise the anchor! Synthesis, X-ray and NMR characterization of 1,3,5-triazinanes with an axial tert-butyl group
dc.creator.none.fl_str_mv Kletskov, Alexey V.
Zatykina, Anastasya D.
Grudova, Mariya V.
Sinelshchikova, Anna A.
Grigoriev, Mikhail
Zaytsev, Vladimir P.
Gil, Diego Mauricio
Novikov, Roman A.
Zubkov, Fedor Ivanovich
Frontera, Antonio
author Kletskov, Alexey V.
author_facet Kletskov, Alexey V.
Zatykina, Anastasya D.
Grudova, Mariya V.
Sinelshchikova, Anna A.
Grigoriev, Mikhail
Zaytsev, Vladimir P.
Gil, Diego Mauricio
Novikov, Roman A.
Zubkov, Fedor Ivanovich
Frontera, Antonio
author_role author
author2 Zatykina, Anastasya D.
Grudova, Mariya V.
Sinelshchikova, Anna A.
Grigoriev, Mikhail
Zaytsev, Vladimir P.
Gil, Diego Mauricio
Novikov, Roman A.
Zubkov, Fedor Ivanovich
Frontera, Antonio
author2_role author
author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv 1,3,5-TRIAZINANES
SULFONAMIDES
NMR ANALYSIS
DFT CALCULATIONS
topic 1,3,5-TRIAZINANES
SULFONAMIDES
NMR ANALYSIS
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 N-t-Bu-N’,N’’-disulfonamide-1,3,5-triazinanes were synthesized and characterized by X-ray single crystal structure analysis. In the course of the X-ray structure elucidation, the first solid experimental evidence of the axial position of the tert-butyl group in unconstrained hexahydro-1,3,5-triazacyclohexanes was obtained. Dynamic low-temperature NMR analysis allowed to fully investigate a rare case of crystallization-driven unanchoring of the tert-butyl group in the chair conformation of saturated sixmembered cycles. DFT calculations show that the use of explicit solvent molecules is necessary to explain the equatorial position of the t-Bu group in solution. Otherwise, the axial conformer is the thermodynamically stable isomer.
Fil: Kletskov, Alexey V.. University of Russia; Rusia
Fil: Zatykina, Anastasya D.. University of Russia; Rusia
Fil: Grudova, Mariya V.. University of Russia; Rusia
Fil: Sinelshchikova, Anna A.. Academy of Sciences; Rusia
Fil: Grigoriev, Mikhail. Academy of Sciences; Rusia
Fil: Zaytsev, Vladimir P.. 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. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica; Argentina
Fil: Novikov, Roman A.. Academy of Sciences; Rusia
Fil: Zubkov, Fedor Ivanovich. University of Russia; Rusia
Fil: Frontera, Antonio. Universidad de las Islas Baleares; España
description N-t-Bu-N’,N’’-disulfonamide-1,3,5-triazinanes were synthesized and characterized by X-ray single crystal structure analysis. In the course of the X-ray structure elucidation, the first solid experimental evidence of the axial position of the tert-butyl group in unconstrained hexahydro-1,3,5-triazacyclohexanes was obtained. Dynamic low-temperature NMR analysis allowed to fully investigate a rare case of crystallization-driven unanchoring of the tert-butyl group in the chair conformation of saturated sixmembered cycles. DFT calculations show that the use of explicit solvent molecules is necessary to explain the equatorial position of the t-Bu group in solution. Otherwise, the axial conformer is the thermodynamically stable isomer.
publishDate 2020
dc.date.none.fl_str_mv 2020-11
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/11336/143341
Kletskov, Alexey V.; Zatykina, Anastasya D.; Grudova, Mariya V.; Sinelshchikova, Anna A.; Grigoriev, Mikhail; et al.; Raise the anchor! Synthesis, X-ray and NMR characterization of 1,3,5-triazinanes with an axial tert-butyl group; Royal Society of Chemistry; Organic & Biomolecular Chemistry; 18; 41; 11-2020; 8386-8394
1477-0520
1477-0539
CONICET Digital
CONICET
url http://hdl.handle.net/11336/143341
identifier_str_mv Kletskov, Alexey V.; Zatykina, Anastasya D.; Grudova, Mariya V.; Sinelshchikova, Anna A.; Grigoriev, Mikhail; et al.; Raise the anchor! Synthesis, X-ray and NMR characterization of 1,3,5-triazinanes with an axial tert-butyl group; Royal Society of Chemistry; Organic & Biomolecular Chemistry; 18; 41; 11-2020; 8386-8394
1477-0520
1477-0539
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/D0OB01201G
info:eu-repo/semantics/altIdentifier/url/https://pubs.rsc.org/en/content/articlelanding/2020/OB/D0OB01201G
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 12.982451

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