Synthesis, structural characterization, antimicrobial activities and theoretical investigations of some 4-(4-aminophenylsulfonyl) phenylimino) methyl)-4-(aryldiazenyl) phenol.
The azo-azomethine dyes with a different substitution have been designed from the reaction of 4,4'-diaminodiphenyl sulfone with 2-hydroxy-5-(aryldiazenyl)benzaldehyde. The compounds have been characterized by elemental analysis, Mass, IR, UV-Vis, TGA-DTA and NMR spectroscopy. The solvatochromism behaviors, effects of substitution and pH on the electronic absorption spectra of dyes were evaluated. The in vitro antimicrobial activities were also screened for their potential for antibiotic activities by broth micro dilution method. Also, the optimum molecular geometries, molecular electrostatic potential (MEP), nucleus-independent chemical shift (NICS) and frontier molecular orbitals (FMO), vibrational spectra (IR ) and electronic absorption (UV-Vis) spectra of the title compounds have been investigated with the help of DFT and TDDFT methods with 6-311++G(d,p) basis sets and PCM calculations. The results of the calculations show excellent agreement with the experimental value.
Department of Chemistry, Faculty of Science, Lorestan University, Khorramabad, Iran; Department of Organic Chemistry, Borujerd Branch, Islamic Azad University, Borujerd, Iran. Electronic address: Mo.ghasemian@yahoo.com.
Motaleb
M
Ghasemian
Department of Chemistry, Faculty of Science, Lorestan University, Khorramabad, Iran.
Ali
A
Kakanejadifard
Department of Organic Chemistry, Borujerd Branch, Islamic Azad University, Borujerd, Iran.
Tahereh
T
Karami
D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D001391:Azo Compounds / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects; D001424:Bacterial Infections / Q000188:drug therapy; D002176:Candida albicans / Q000187:drug effects; D002177:Candidiasis / Q000188:drug therapy; D006801:Humans; D008745:Methylation; D008958:Models, Molecular; D010636:Phenols / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D013882:Thiosemicarbazones / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*
D000890:Anti-Infective Agents; D001391:Azo Compounds; D010636:Phenols; D013882:Thiosemicarbazones; C512188:azomethine
Antimicrobial activity; Azo-azomethines dye; Density functional theory; PCM; Solvatochromism; TDDFT; Tautomerism