The synthesis, structural characterization and antibacterial properties of some 2-((4-amino-1,2,5-oxadiazol-3-ylimino)methyl)-4-(phenyldiazenyl)ph e nol

• Published in: Dyes and pigments Vol. 97; no. 1; pp. 215 - 221
• Main Authors: Kakanejadifard, Ali, Azarbani, Farideh, Zabardasti, Abedien, Kakanejadifard, Sahar, Ghasemian, Motaleb, Esna-ashari, Fatemeh, Omidi, Sakineh, Shirali, Somayeh, Rafieefar, Maryam
• Format: Journal Article
• Language: English
• Published: 01.04.2013
• Subjects: Absorption spectra; Bacillus; Bacteria; Mathematical analysis; Methyl alcohol; Phenol; Quantum chemistry; Solvents; Staphylococcus aureus
• ISSN: 0143-7208

The Schiff base compounds 2-((4-amino-1,2,5-oxadiazol-3-ylimino)methyl)-4-(phenyldiazenyl) phenol (2aae) were prepared from the reaction of 3,4-diamino-1,2,5-oxadiazole with 2-hydroxy-5-[(E)-(aryldiazenyl)]benzaldehyde (1aae) in methanol. The structures of all compounds were then characterized by elemental analysis, mass, IR, UV-Vis, 1H and 13C NMR spectroscopy. UV-Vis absorption spectra indicated enolaketo tautomeric and positive solvatochromism in compound 2aae which is dependent on the substitution, nature of solvent, pH and environment temperature. The Quantum chemical calculations and UV-Vis absorption spectra data show that positive solvatochromism behavior of compounds 2aae, which could be due to intramolecular hydrogen bond in enolaketo tautomeric and dipole moment changes. The antibacterial activities of compounds were evaluated against both gram-positive and gram-negative bacteria. All the compounds were found to be active against Staphylococcus aureus and Bacillus cereuss. Among them, compound 2b exhibited the most potent antibacterial activity.