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

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