Abstract

CAGLIERI, Silvana Claudia  and  MACANO, Héctor Rubén. Reactivity of amines in acetylation catalyzed by Lewis acids and influence of solvents: theoretical study. Ing. invest. y tecnol. [online]. 2018, vol.19, n.2, pp.239-244. ISSN 2594-0732.  https://doi.org/10.22201/fi.25940732e.2018.19n2.020.

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.

Keywords : Acetylation, amine, amide; UFF, Lewis acid, DFT, IEFPCM.

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