Reactividad de aminas en la acetilación catalizada por ácidos de Lewis e influencia de solventes: estudio teórico
Date
2018
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Abstract
Se llevó a cabo un estudio teórico comparativo de reactividad de etilamina y anilina, frente a la reacción de acetilación catalizada
por iones metálicos: Zn2+; Co2+, Mn2+; Cu2+ y Ni2+, a través del análisis de los intermediarios de reacción correspondientes. Las
energías de activación y las energías de los intermediarios de reacción, se calcularon con el método Universal Force Field (UFF). Los
valores obtenidos se compararon con datos de literatura. La etilamina presentó la mayor reactividad frente a la acetilación en todos
los casos y el Zn2+ resultó ser el ion metálico más reactivo, reportando los valores más bajos de energía. Se completó el estudio comparando la reactividad de etilamina y anilina frente a la reacción de acetilación, en presencia de diferentes solventes polares, a través
del análisis de los intermediarios de reacción correspondientes. Las energías de los mismos y las energías de activación se calcularon
con el nivel de teoría funcional de densidad (DFT) con el estándar B3LYP combinado con los conjuntos de base 3-21G* y 6-31G*.
Para estudiar la influencia de los diferentes solventes se utilizó el modelo IEFPCM. Los valores obtenidos se compararon con datos de
literatura. La etilamina presentó la mayor reactividad en todos los casos y el acetonitrilo resultó ser el solvente más óptimo para la
reacción de acetilación de ambas aminas.
A comparative theoretical study of reactivity of ethylamine and aniline in the acetylation reaction catalized by metallic ions: Zn2+; Co2+, Mn2+; Cu2+ y Ni2+, through the analysis of the corresponding reaction intermediates was carried out. The activation and the reaction intermediates energies were calculated with the Universal Force Field (UFF) method. The calculated values were compared with literature data. The ethylamine presented the higher reactivity in the acetylation reaction and lower energy values were obtained in the catalysis by Zn2+. Further theoretical studies comparing the reactivity of ethylamine and aniline in the acetylation reaction as a function of the solvent polarity were performed through the analysis of the corresponding reaction intermediates. The activation and the reaction intermediates energies were calculated with the level density functional theory (DFT) with the standard B3LYP combined with basis set 3-21G* and 6-31G*. The IEFPCM model used to study the influence of different solvents. The values obtained were compared with literature data. The ethylamine presented the higher reactivity in the acetylation reaction and the acetonitrile turned out to be the best solvent for the reaction of acetylation of both amines.
A comparative theoretical study of reactivity of ethylamine and aniline in the acetylation reaction catalized by metallic ions: Zn2+; Co2+, Mn2+; Cu2+ y Ni2+, through the analysis of the corresponding reaction intermediates was carried out. The activation and the reaction intermediates energies were calculated with the Universal Force Field (UFF) method. The calculated values were compared with literature data. The ethylamine presented the higher reactivity in the acetylation reaction and lower energy values were obtained in the catalysis by Zn2+. Further theoretical studies comparing the reactivity of ethylamine and aniline in the acetylation reaction as a function of the solvent polarity were performed through the analysis of the corresponding reaction intermediates. The activation and the reaction intermediates energies were calculated with the level density functional theory (DFT) with the standard B3LYP combined with basis set 3-21G* and 6-31G*. The IEFPCM model used to study the influence of different solvents. The values obtained were compared with literature data. The ethylamine presented the higher reactivity in the acetylation reaction and the acetonitrile turned out to be the best solvent for the reaction of acetylation of both amines.
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Keywords
Acetilación, Amina, Amida, UFF, Ácido Lewis, DFT, IEFPCM
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Ingenierìa Investigación y Tecnología
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