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
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/143341
Ver los metadatos del registro completo
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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 Técnicas2025-09-29T10:17:20Zoai: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:34982025-09-29 10:17:20.759CONICET 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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13.070432 |