Artículo
Raise the anchor! Synthesis, X-ray and NMR characterization of 1,3,5-triazinanes with an axial tert-butyl group
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
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Fecha de publicación:
11/2020
Editorial:
Royal Society of Chemistry
Revista:
Organic & Biomolecular Chemistry
ISSN:
1477-0520
e-ISSN:
1477-0539
Idioma:
Inglés
Tipo de recurso:
Artículo publicado
Clasificación temática:
Resumen
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.
Palabras clave:
1,3,5-TRIAZINANES
,
SULFONAMIDES
,
NMR ANALYSIS
,
DFT CALCULATIONS
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Colecciones
Articulos(INBIOFAL)
Articulos de INSTITUTO DE BIOTECNOLOGÍA FARMACEUTICA Y ALIMENTARIA
Articulos de INSTITUTO DE BIOTECNOLOGÍA FARMACEUTICA Y ALIMENTARIA
Citación
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
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