Abstract

CAGLIERI, Silvana C  and  MACANO, Héctor R. Aliphatic and Aromatic Amines Acetylation: Theoretical Study. Inf. tecnol. [online]. 2016, vol.27, n.2, pp.105-110. ISSN 0718-0764.  http://dx.doi.org/10.4067/S0718-07642016000200013.

A comparative theoretical study of reactivity of methylamine, aniline, diphenylamine, p-nitroaniline and p-methylaniline acetylation, through the analysis of the corresponding reaction intermediates was carried out. The acetylation of amines is one of the most frequently used transformations in organic synthesis since it provides an efficient and inexpensive means for protecting amino group in a synthetic process. The activation energies and the reaction intermediates energies were calculated with two levels of theory: density functional theory (DFT) with the standard B3LYP and the Møller-Plesset perturbation theory (MP2) combined with the basis set 6-31G*. The calculated values were compared with literature data. The methylamine presented the higher reactivity in the acetylation reaction and the DFT method gave the lower energy values.

Keywords : acetylation; amine; density functional theory (DFT); Møller-Plesset perturbation theory (MP2).

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