Zeitschrift fur Naturforschung, B: Chemical Sciences p. 159 - 164 (2012)
Update date:2022-08-02
Topics: Synthesis Elemental analysis Characterization Melting point Crystallization Yield Distillation Isolation Mass spectrometry Selectivity Molecular docking Steric hindrance Chromatography Recrystallization Drying agent Boiling point Hydrolysis Solubility Elution Filtration Capillary column Intramolecular hydrogen bonding Regression analysis Correlation coefficient TLC (thin-layer chromatography) HPLC (high-performance liquid chromatography) NMR (nuclear magnetic resonance) Proton transfer Resolution X-ray crystallography Thermochromism Tautomerism Chelation Density functional theory (DFT) Detector Purification Isomerization Conjugation Workup Condensation Reaction Mobile Phase Reaction Mechanism UV-Vis Spectroscopy Reaction Kinetics Documentation Dehydration Reaction Calibration Catalysis Sensitivity Reaction Monitoring
Hamidian, Kourosh
Irandoust, Mohsen
Rafiee, Ezzat
Joshaghani, Mohammad
The primary azo compound 1-(3-formyl-4-hydroxyphenylazo)-4-nitrobenzene reacts with some aliphatic and aromatic diamines and yields the corresponding azo-azomethine compounds. These compounds were characterized by elemental analysis, IR, UV/Vis, and NMR spectroscopy. The primary azo compound exists entirely in the azo form in solution as well as in the solid phase. The tautomeric structure of azo-azomethine compounds heavily depends on the solvent and the substituents. Aliphatic diamine-based compounds favor the enol-imine tautomer while aromatic diamine-based compounds have structures that lie between the two enol-imine and keto-amine tautomers due to a relatively strong intramolecular hydrogen bond. The compounds exhibit positive solvatochromism (bathochromic shift) so that their absorption bands move toward longer wavelengths as the polarity of the solvents increases. In addition, UV/Vis spectrophotometry has shown that the studied compounds have molar extinction coefficients larger than 40000.
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(2012)