NMR Study of the dynamic equilibria among isomeric species in quinoxalin-2-one derivatives

The understanding of the prototropic lactam/lactim/enol equilibrium and the E/Z isomerism around the N-C(O) bond in amides is important for the determination of different physicochemical properties in compounds, moreover in compounds with more than one equilibrium. In this work, these equilibria wer...

Descripción completa

Guardado en:
Detalles Bibliográficos
Autores principales: Barrionuevo, Emiliano, Jasinski, Gabriel, Fabian, Lucas, Martini, M. Florencia, Moglioni, Albertina
Formato: Artículo de publicación periódica
Lenguaje:Inglés
Publicado: 2024
Materias:
QUINOXALINA
MODELADO MOLECULAR
NMR
EQUILIBRIO DINÁMICO
ESPECIES ISOMÉRICAS
Acceso en línea:https://ri.itba.edu.ar/handle/20.500.14769/4470
Aporte de:
Repositorio Institucional Instituto Tecnológico de Buenos Aires (ITBA) de Instituto Tecnológico de Buenos Aires (ITBA)
id I32-R138-20.500.14769-4470
record_format dspace
spelling I32-R138-20.500.14769-44702026-01-15T14:53:37Z NMR Study of the dynamic equilibria among isomeric species in quinoxalin-2-one derivatives Barrionuevo, Emiliano Jasinski, Gabriel Fabian, Lucas Martini, M. Florencia Moglioni, Albertina QUINOXALINA MODELADO MOLECULAR NMR EQUILIBRIO DINÁMICO ESPECIES ISOMÉRICAS The understanding of the prototropic lactam/lactim/enol equilibrium and the E/Z isomerism around the N-C(O) bond in amides is important for the determination of different physicochemical properties in compounds, moreover in compounds with more than one equilibrium. In this work, these equilibria were studied for N-acyl and N-carbamoyl-3,4-dihydroxyquinoxalin-2(1H)-ones using mono- and bi-dimensional NMR experiments, at different temperatures. For both types of derivatives, the lactam form was the only tautomer detected. The results obtained from molecular modelling experiments agree with the experimental results. For the N-acyl derivative, the E isomer is the predominant, while for the N-carbamoyl derivative both geometric isomers are present in a similar ratio. The theoretical calculations allowed the signal assignment for each isomer from the chemical shift values estimated for both geometric isomers corresponding to the studied N-acyl and N-carbamoyl derivatives. 2024-06-13T15:57:24Z 2024-06-13T15:57:24Z 2024 Artículo de publicación periódica https://ri.itba.edu.ar/handle/20.500.14769/4470 en application/pdf
institution Instituto Tecnológico de Buenos Aires (ITBA)
institution_str I-32
repository_str R-138
collection Repositorio Institucional Instituto Tecnológico de Buenos Aires (ITBA)
language Inglés
topic QUINOXALINA
MODELADO MOLECULAR
NMR
EQUILIBRIO DINÁMICO
ESPECIES ISOMÉRICAS
spellingShingle QUINOXALINA
MODELADO MOLECULAR
NMR
EQUILIBRIO DINÁMICO
ESPECIES ISOMÉRICAS
Barrionuevo, Emiliano
Jasinski, Gabriel
Fabian, Lucas
Martini, M. Florencia
Moglioni, Albertina
NMR Study of the dynamic equilibria among isomeric species in quinoxalin-2-one derivatives
topic_facet QUINOXALINA
MODELADO MOLECULAR
NMR
EQUILIBRIO DINÁMICO
ESPECIES ISOMÉRICAS
description The understanding of the prototropic lactam/lactim/enol equilibrium and the E/Z isomerism around the N-C(O) bond in amides is important for the determination of different physicochemical properties in compounds, moreover in compounds with more than one equilibrium. In this work, these equilibria were studied for N-acyl and N-carbamoyl-3,4-dihydroxyquinoxalin-2(1H)-ones using mono- and bi-dimensional NMR experiments, at different temperatures. For both types of derivatives, the lactam form was the only tautomer detected. The results obtained from molecular modelling experiments agree with the experimental results. For the N-acyl derivative, the E isomer is the predominant, while for the N-carbamoyl derivative both geometric isomers are present in a similar ratio. The theoretical calculations allowed the signal assignment for each isomer from the chemical shift values estimated for both geometric isomers corresponding to the studied N-acyl and N-carbamoyl derivatives.
format Artículo de publicación periódica
author Barrionuevo, Emiliano
Jasinski, Gabriel
Fabian, Lucas
Martini, M. Florencia
Moglioni, Albertina
author_facet Barrionuevo, Emiliano
Jasinski, Gabriel
Fabian, Lucas
Martini, M. Florencia
Moglioni, Albertina
author_sort Barrionuevo, Emiliano
title NMR Study of the dynamic equilibria among isomeric species in quinoxalin-2-one derivatives
title_short NMR Study of the dynamic equilibria among isomeric species in quinoxalin-2-one derivatives
title_full NMR Study of the dynamic equilibria among isomeric species in quinoxalin-2-one derivatives
title_fullStr NMR Study of the dynamic equilibria among isomeric species in quinoxalin-2-one derivatives
title_full_unstemmed NMR Study of the dynamic equilibria among isomeric species in quinoxalin-2-one derivatives
title_sort nmr study of the dynamic equilibria among isomeric species in quinoxalin-2-one derivatives
publishDate 2024
url https://ri.itba.edu.ar/handle/20.500.14769/4470
work_keys_str_mv AT barrionuevoemiliano nmrstudyofthedynamicequilibriaamongisomericspeciesinquinoxalin2onederivatives
AT jasinskigabriel nmrstudyofthedynamicequilibriaamongisomericspeciesinquinoxalin2onederivatives
AT fabianlucas nmrstudyofthedynamicequilibriaamongisomericspeciesinquinoxalin2onederivatives
AT martinimflorencia nmrstudyofthedynamicequilibriaamongisomericspeciesinquinoxalin2onederivatives
AT moglionialbertina nmrstudyofthedynamicequilibriaamongisomericspeciesinquinoxalin2onederivatives
_version_ 1865139421796368384

Ejemplares similares