Abstract
The complexes of the Schiff base of racemic gossypol with 5-hydroxy-3-oxapentylamine (GSBH) with H + and monovalent metal cations were synthesized and studied ESI mass spectrometry and the PM5 semiempirical calculation. The Schiff base studied exists in chloroform solution in the enamine–enamine tautomeric form. After protonation the tautomeric form changes into the imine–imine one. The GSBH molecule form 1:1 complexes with Li +, K + and Rb + cations in which the enamine–enamine tautomeric form is favoured. The structures of the protonated Schiff base and its complex with Li + and K + cation as well as the respective hydrogen bonds within these structures are discussed.
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