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Química Nova

Print version ISSN 0100-4042On-line version ISSN 1678-7064


ESTEVES-SOUZA, Andressa; ECHEVARRIA, Aurea; SANT'ANNA, Carlos Mauricio R.  and  NASCIMENTO, Maria da Graça. Experimental and theoretical study of the reduction of Schiff bases derivated from 3,3-diphenylpropilamine. Quím. Nova [online]. 2004, vol.27, n.1, pp.72-75. ISSN 0100-4042.

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.

Keywords : Schiff bases; 3,3-diphenylpropylamines; semi-empirical methods.

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