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1 2009

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Structure of a New Schiff Base of Gossypol with Ethyl 4-Amino-1-piperidine Carboxylate in the Solid and in the Solution

Przybylski P., Pyta K., Ratajczak-Sitarz M., Katrusiak A., Brzezinski B.

Polish Journal of Chemistry

2009

Vol. 83, nr 5

747-759

Crystals of the Schiff base derivative of gossypol with ethyl 4-amino-1-piperidine carboxylate (GSPC) have been grown and subsequently examined by X-ray diffraction, FT-IR and NMR methods. The crystal space group is P21/n with a = 11.869(1) A, b = 13.540(1) capital A, ring c = 28.119(1) capital A, ring, beta = 91.22(1)° and Z = 4. In the crystal GSPC exists in the enamine-enamine tautomeric form. The intramolecular N(16)–H(16)źźźO(2), N(16’)–H(16’)źźźO(2’) hydrogen bonds assisted by the resonance of the pi-electrons in the aromatic system are the strongest. The FT-IR spectral features of the crystals are in agree - ment with the X-ray data indicating that both parts of the molecule are similarly intramolecular hydrogen-bonded but different intermolecular hydrogen-bonded, al - though the molecule is symmetrically substituted. The FT-IR as well as 1H and 13C NMR spectra have shown that in chloroform solution the enamine-enamine tautomeric form is preserved and the whole structure of GSPC be comes more symmetrical.