title: Phenylazoindole dyes--part I: the syntheses, characterizations, crystal structures, quantum chemical calculations and antimicrobial properties.
abstract: In this study, the synthesis of four new phenylazo indole dyes (dye 1-4) were carried out by diazotization of 4-aminoacetophenone and coupling with various 2- and 1,2-disubstituted indole derivatives. The dyes were characterized by UV-vis, FT-IR, (1)H NMR, HRMS and X-ray single crystal diffraction methods. Azo-hydrazone tautomeric bahavior of the dyes in different solvents (DMSO, methanol, acetic acid and chloroform) was investigated by using (1)H NMR and UV-vis results. The experimental results were compared with the corresponding calculated values. The results of experimental data and theoretical calculations showed that the azo tautomer is more stable than hydrazone tautomer. In addition to this, the antimicrobial activity of the dyes was also evaluated.
authors.affiliation: Gazi University, Department of Chemistry, 06500 Ankara, Turkey. znseferoglu@gazi.edu.tr
authors.forename: Zeynel
authors.initials: Z
authors.lastname: Seferoğlu
authors.forename: Ergin
authors.initials: E
authors.lastname: Yalçın
authors.forename: Banu
authors.initials: B
authors.lastname: Babür
authors.forename: Nurgül
authors.initials: N
authors.lastname: Seferoğlu
authors.forename: Tuncer
authors.initials: T
authors.lastname: Hökelek
authors.forename: Ebru
authors.initials: E
authors.lastname: Yılmaz
authors.forename: Ertan
authors.initials: E
authors.lastname: Şahin
mesh_terms: D000042:Absorption; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D004396:Coloring Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D018360:Crystallography, X-Ray; D004121:Dimethyl Sulfoxide / Q000737:chemistry; D005658:Fungi / Q000187:drug effects; D006860:Hydrogen Bonding; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D008968:Molecular Conformation; D011789:Quantum Theory; D012996:Solutions; D012997:Solvents; D013237:Stereoisomerism; D013816:Thermodynamics
chemical_list: D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents; D000935:Antifungal Agents; D004396:Coloring Agents; D007211:Indoles; D012996:Solutions; D012997:Solvents; C008844:phenylazoindole; D004121:Dimethyl Sulfoxide
keywords: Antimicrobial activity; Azo–hydrazone tautomer; Crystal structure; DFT calculations; Phenylazoindole dye