aFaculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznan, Poland
bInstitute of Medical Physics and Biophysics, Universitätsklinikum Charité, Humboldt University, ZiegelStr. 5-9, D-10098 Berlin, Germany
Abstract:
A new hydrazone of gossypol with 3,6-dioxaheptylhydrazine (GHDO) has been synthesised and its structure has been studied by FT-IR, 1H NMR, 13C NMR as well as PM5 semiempirical methods. All the studies have provided clear evidence of the existence of GHDO in the solution in the N-imine–N-imine tautomeric form. The structure and the spectroscopic behaviour of this tautomer are discussed in details. It is shown the structure of GHDO is strongly stabilised by different types of intramolecular hydrogen bonds. In two of them the oxygen atoms of the oxaalkyl chains are also engaged. The strongest intramolecular hydrogen bond is formed between the O7H proton and N16 atom from the hydrazone group.