Abstract
Hydrazone of gossypol with hydrazine (GH) has been synthesised and its structure has been studied by 1H NMR, 13C NMR, 13C CP-MAS, 15N CP-MAS, FT-IR and PM5 semiempirical methods. The results have shown that the simplest hydrazone of gossypol exists both in solution and in solid in the N-imine– N-imine tautomeric form, stabilized by several intramolecular hydrogen bonds among which the O 7H ···N 16 intramolecular one is the strongest. The structure of GH is visualized by the PM5 semiempirical calculations. The ESI-MS studies have shown that the GH molecule can be present in the mono- and di-protonated forms. It is demonstrated that the protonation occurs at the amino groups of GH molecule and has no influence on the intramolecular hydrogen bonds within the N-imine– N-imine tautomeric form.
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