Resonance Raman spectra of 2‐(2‐pyridylazo)‐5‐diethylaminophenol and its complex at various pH values

The structure of 2‐(2‐pyridylazo)‐5‐diethylaminophenol (PADAP) and its complex at various pH values was studied by resonance Raman spectroscopy. The spectral features are sensitive to the pH and the solvent, which can be explained in terms of azo–hydrazone tautomers. Two types of quinonoid structures are found under neutral conditions: a hydrazone structure in chloroform solution and a pyridone‐like structure with an NH bond in the pyridine ring in aqueous solution. The quinoid structure is found at both pH 0.1 and 2.3. The relationship between the structure and the absorption spectrum under neutral conditions is discussed on the basis of CNDO/2 calculations.