Abstract
The interaction of hexa-2,4-dienylideneisopropylamine and 3-phenylprop-2-enylideneisopropylamine with phenol derivatives (pKa = 10.30−0.4) was investigated in solution by Fourier transform IR spectrometry. The influence of hydrogen bond formation on the frequency and intensity of the CN stretching vibration is discussed. The thermodynamic parameters for the normal hydrogen bonds and for the proton transfer complexes were determined; 50% proton transfer is achieved for ΔpKa values of about 2 for both imine systems. The lowest OH stretching frequencies corresponding to a delocalized proton are observed at about the same ΔpKa values.
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