Abstract

The reaction of 5-bromo-4-nitrofuraldehyde (4-NO2) with (eta(5)-C5H4NH2)Fe(eta(5)-C5H5) produces the Schiff base [(eta(5)-C5H4)-NCH-(Br-NO2-2-C4HO)]Fe(eta(5)-C5H5) (1a) as a condensation product and the amine complex [(eta(5)-C5H4)-NH-(CHO-NO2-2-C4HO)]Fe(eta(5)-C5H5) (1b) as a substitution product in a 1:4 ratio, whereas the reaction between 4-bromo-5-nitrofuraldehyde (5-NO2) and (eta(5)-C5H4NH2)Fe(eta(5)-C5H5) generates only the iminic derivative (2a). The structures of all the complexes were inferred from their FT-IR, H-1 NMR, C-13 NMR and mass spectra. The molecular structure of the ferrocenylamine (1b) determined by X-ray crystallography showed an unusual intramolecular H-bond (N-HO), an [(eta(5)-C5H4)-NH-(CHO-C4HO-NO2)] planar system, and an sp(2)-type hybridization on the amine nitrogen. Cyclic voltammetry study of 5-nitrofuran derivative 2a, exhibits a more anodic reduction potential (E = -0.60 V) compared with those registered for 1a (E = -1.03 V) and 1b (E = -1.14 V). All compounds were tested for their anti-parasitic activity against the tripomastigote form of the Dm28c strain of T. cruzi.(C) 2019 Elsevier B.V. All rights reserved.