Abstract
A new Schiff base of gossypol with 5-hydroxy-3-oxapentylamine (GSBH) has been found to complex bivalent metal cations, in particular Ca 2+, Ba 2+ and Pb 2+. This process of complex formation has been studied by ESI mass spectrometry, 1H, 13C NMR and FT-IR spectroscopy as well as by PM5 semiempirical method. It has been established that GSBH forms stable 1:1 complexes with all these cations. In all complexes the Schiff base of gossypol exists as the enamine–enamine tautomer. The Ca 2+, Ba 2+ cations are coordinated through oxygen atoms from the four hydroxyl groups, and Pb 2+ cation additionally also by two oxygen atoms from oxaalkyl chains. The structures of these complexes have been calculated by PM5 semiempirical method and discussed.
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