The reaction of 2-hydroxy-5-(pyridine-4-yldiazenyl)benzaldehyde with n-alkyl bromides generated five novel azo pyridinium salts in good to excellent yields. The 1 H and 13 C NMR and UV-Vis absorption spectra indicated several tautomers for the new compounds. The NMR, UV-Vis absorption spectra and quantum chemical calculations show that the azo pyridinium salts have a new resonant structure compared to the corresponding azo precursor. Antibacterial activity was studied by disc diffusion and MIC methods. Diphenylpicrylhydrazyl (DPPH) assay was used to determine the antioxidant properties. The effects of carbon chain length on antimicrobial activity were also investigated. The results showed that existence of alkyl groups is crucial for the antibacterial properties. The new compound with decyl group displayed the best antibacterial activity. prepared and purified according to the method reported in the literature. 19 Melting points were measured on an Electrothermal 9200 apparatus. Mass spectra were recorded on an Agilent MS Model 5973. FT-IR spectra were recorded on a Shimadzu 8400S spectrometer using KBr disc. The electronic absorption spectra were recorded with a Shimadzu 1650 spectrophotometer. 1 H and 13 C NMR spectra were recorded in DMSO-d 6 as the solvent on the Bruker DRX-300 MHz and 400 MHz Advance spectrometers.
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