Abstract

The Schiff base of racemic gossypol with l-phenylalanine methyl ester and its complexes with H + and monovalent metal cations was synthesized and studied by FT-IR, 1H NMR spectroscopy and Electrospray Ionization mass spectrometry as well as by the PM5 semi-empirical method. The studied Schiff base exists in acetonitrile solution in the enamine–enamine tautomeric form. After the protonation, the tautomeric form changes into the imine–imine one. For this form of the Schiff base the existence of diastereoisomers was very well visible in the 1H NMR spectra. The structures of the protonated Schiff base and its 1:1 complex with K + cation as well as the respective hydrogen bonds within these structures are discussed.

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