Estudo experimental e teórico da redução de bases de Schiff derivadas da 3,3-difenilpropilamina

AUTOR(ES)

Esteves-Souza, Andressa, Echevarria, Aurea, Sant'Anna, Carlos Mauricio R., Nascimento, Maria da Graça

FONTE

Química Nova

DATA DE PUBLICAÇÃO

2004-02

RESUMO

A series of seven Schiff bases have been synthesized from 3,3-diphenylpropilamine and substituted benzaldehydes. These imines were treated with NaBH4 in ethanol affording the corresponding amines in 98-55% yields. A molecular modeling study was performed with the Schiff bases in order to compare the theoretical parameters with the experimental results. The theoretical parameters were obtained by AM1 and PM3 semi-empirical methods. The analysis of charge, electron densities and LUMO coefficients suggested that the most favorable interactions should occur with Schiff bases containing electron-donating groups, in accordance with experimental yields, showing that the higher reactivity is due to higher electrophilic character of imine carbons.

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