Synthesis, characterization and antimicrobial studies of 2-{(E)-[(2-hydroxy-5-methylphenyl)imino]methyl}-4-[(E)-phenyldiazenyl] phenol as a novel azo-azomethine dye

Abstract

A novel dye, 2-{(E)-[(2-hydroxy-5-methylphenyl)imino]methyl}-4-[(E)-phenyldiazenyl]phenol dye was synthesized by the condensation reaction of 2-hydroxy-5-[(E)-phenyldiazenyl]benzaldehyde with 2-amino-4-methylphenol in methanol. The title dye was characterized by its melting point, elemental analysis, FT-IR, H-1, C-13 NMR and mass spectroscopic studies. Molecular structure of the title dye was determined by single crystal X-ray diffraction study. X-ray data showed that the dye crystallizes in the monoclinic space group P2(1)/c with cell parameters a = 18.541(2) angstrom, b = 4.7091(5) angstrom, c = 20.586(2) angstrom, V = 1761.5(3) angstrom(3) and Z = 4. The title dye adopts azo-enamine tautomer in the solid state. The molecules crystallises as dimers assembled by two molecules of methanol via intermolecular hydrogen bonding resulting in R-6(4)(18) hydrogen bonding motif. Additionally, there is an intramolecular keto-amine hydrogen bond (NH...O) with a distance of 2.6172(17) angstrom. Optimized structures of the three possible tautomers of the compound were obtained using B3LYP method with 6-311++G(d,p), 6-31G and 3-21G basis sets in the gas phase. Thermal properties of the prepared dye were examined by thermogravimetric analysis and results indicated that the framework of the dye is stable up to 172 degrees C. Furthermore, the pathogenic activities of the synthesized dye were tested in vitro against the sensitive organisms, Bacillus cereous (ATCC 33019) and Staphylococcus aureus (ATCC 25923) as gram positive bacteria, Escherichia coli (ATCC 11229), and Klebsiella pneumoniae (ATCC 13883) as gram negative bacteria and the results are discussed. The results indicated that the prepared dye had antibacterial activities against gram-positive bacteria (S. aureus and Bacillus cereuss), but it exhibited no activity against gram-negative bacteria (E. coli and K. pneumoniae). (C) 2013 Elsevier B.V. All rights reserved.