Spectroscopic and semiempirical studies of new Schiff base of gossypol with allylamine in solution |
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Authors: | Piotr Przybylski, Maria Ma uszyn ska,Bogumi Brzezinski |
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Affiliation: | Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60 780 Poznan, Poland |
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Abstract: | The Schiff base of racemic gossypol with allylamine (GSBAL) has been studied by FT-IR, 1H and 13C NMR spectroscopy as well as by the PM5 semiempirical method. The spectroscopic methods have shown that GSBAL Schiff base exists in chloroform solution as enamine–enamine tautomer. The structure of GSBAL and the hydrogen bonds within this structure have been calculated to show that the allyl groups are out-of-planes of naphthalene rings. The strongest intramolecular hydrogen bond within the structure of GSBAL is formed between O7H–N16 atoms and it belongs to the medium strong bonds. The other hydrogen bonds, although very weak, play a very important role in stabilising the GSBAL enamine–enamine structure. |
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Keywords: | Gossypol Schiff bases Allylamine 1H NMR 13C NMR COSY HETCOR FT-IR PM5 semiempirical calculation Hydrogen bonds |
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