ABSTRACT:A relationship between the chemical structure and antibacterial activity of nitrofurans is not still completely elucidated; however, from a therapeutics point of view it has been observed that the position of the nitro group is a relevant feature for them to show antibacterial activity. In this work, we performed an ab initio study of some selected nitrofurans at the Hartree-Fock, second-order Møller-Plesset, and Density Functional levels of theory with the purpose of obtaining several electronic structural and physicochemical properties of nitrofurans. The relative acidity of the azomethine group of nitrofurans was analyzed through the deprotonation energy. The results reveal that the less acidic molecules possess antibacterial activity. The bond order analysis suggests that the activity of the nitrofurans could be affected by the electroattracting properties of the substituent. An atomic charge and electrostatic potential analysis showed that the azomethine group, the nitro group, and the furenic ring are influenced by the substituent electronegativity. Finally, a structural analysis showed that the nitro group is coplanar with respect to the furenic ring. The present study reveals that the analyzed physicochemical and structural properties may be related to the antibacterial activity of these nitrofuran-type compounds.