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Titre du document / Document title

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

Auteur(s) / Author(s)

PRZYBYLSKI P. ; PYTA K. ; RATAJCZAK-SITARZ M. ; KATRUSIAK A. ; BRZEZINSKI B. ;

Résumé / Abstract

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) A, c = 28.119(1) A, β = 91.22(1)° and Z = 4. In the crystal GSPC exists in the enamine-enamine tautomeric form. The intramolecular N(16)―H(16)···O(2), N(16')―H(16')···O(2') hydrogen bonds assisted by the resonance of the π-electrons in the aromatic system are the strongest. The FT-IR spectral features of the crystals are in agreement with the X-ray data indicating that both parts of the molecule are similarly intramolecular hydrogen-bonded but different intermolecular hydrogen-bonded, although 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 becomes more symmetrical.

Revue / Journal Title

Polish journal of chemistry    ISSN  0137-5083 

Source / Source

2009, vol. 83, no5, pp. 747-759 [13 page(s) (article)]

Langue / Language

Anglais

Editeur / Publisher

Polish Chemical Society, Warsaw, POLOGNE  (1978) (Revue)

Mots-clés d'auteur / Author Keywords

gossypol

;

Schiff base

;

X-ray

;

FT-IR

;

1H

;

13C NMR

;

Localisation / Location

INIST-CNRS, Cote INIST : 4711, 35400018711789.0040

Nº notice refdoc (ud4) : 21648244



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