Complexes of Schiff base of gossypol with n-butylamine and some monovalent or bivalent cations studied by ESI MS, NMR, FT-IR as well as PM5 semiempirical methods |
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Authors: | Piotr Przybylski Rados?aw Pankiewicz Franz Bartl |
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Institution: | a Faculty of Chemistry, A. Mickiewicz University, Grunwaldzka 6, 60-780 Poznan, Poland b Institute of Medical Physics and Biophysics, Universitätsklinikum Charité, Humboldt University, ZiegelStr. 5-9, D-10098 Berlin, Germany |
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Abstract: | A Schiff base of gossypol with n-butylamine GSBN] was shown to be capable of complexation of 2H+, Li+, Ca2+ and Ba2+ cations. This process of complex formation was studied by ESI mass spectrometry, 1H and 13C NMR and FT-IR spectroscopy as well as by PM5 semiempirical method. It was found that gossypol Schiff base can form a 1:2 complex with H+ and 1:1 complexes with Li+, Ca2+ and Ba2+ cations. In all complexes the Schiff base of gossypol with metal cations exists in enamine-enamine tautomer, whereas in the 1:2 complex with H+ the imine-imine tautomer was found. The metal cations are coordinated through oxygen atoms of the O1H(O1,H) hydroxyl groups and a lone pair of an N-atom. The structures of these complexes were calculated by PM5 semiempirical method and discussed. |
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Keywords: | Gossypol Gossypol Schiff base n-butylamine Gossypol Schiff base complexes Monovalent cations Bivalent cations FT IR 1H NMR COSY 13C NMR ESI MS PM5 calculation |
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