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

• Autorzy: Przybylski P. , Pyta K. , Ratajczak-Sitarz M. , Katrusiak A. , Brzezinski B.
• Języki publikacji: EN

Abstrakty

EN

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.

Słowa kluczowe

EN

gossypol; Schiff base; X-ray; FTIR; 1H; 13C NMR

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2009
• Tom: Vol. 83, nr 5
• Strony: 747--759
• Opis fizyczny: Bibliogr. 43 poz., rys.

Twórcy

autor

Przybylski P.

autor

Pyta K.

autor

Ratajczak-Sitarz M.

autor

Katrusiak A.

autor

Brzezinski B.

• Faculty of Chemistry, A. Mickiewicz Uni ver sity, Grunwaldzka 6, 60-780 Poznan, Poland Tel: [phone], Fax: [phone],

Bibliografia

• 1. Filarowski A., Koll A, Hansen P.E. and Kluba M, J. Phys. Chem. A, 112, 3478 (2008).
• 2. Koll A, Karpfen A. and Wolschann P., J. Mol. Struct., 268, 844 (2007).
• 3. Koll A., Karpfen A. and Wolschann P., J. Mol. Struct, 55, 790 (2006).
• 4. Mukhopadhyay M, Banerjee D, Koll A, Filarowski A. and Mukherjee S, Spectrochim. Acta - Part A, 62, 126 (2005).
• 5. Filarowski A, Kochel A, Cieślik K. and Koll A, J. Phys. Org. Chem., 18, 986 (2005).
• 6. Filarowski A, Koll A., Rospenk M., Krol-Starzomska I. and Hansen P.E, J. Phys. Chem. A, 109,4464 (2005).
• 7. Jański J. and Koll A, Struct. Chem., 15, 353 (2004).
• 8. Krol-Starzomska I, Filarowski A, Rospenk M, Koll A. and Melikova S, J. Phys. Chem. A, 108,2131 (2004).
• 9. Filarowski A, Koll A., Karpfen A. and Wolschann P, Chem. Phys., 297, 323 (2004).
• 10. Koll A, Int. J. Mol. Set, 4,434 (2003).
• 11. Sobczyk L., Grabowski S.J. and Krygowski T.M., Chem. Rev., 105, 3513 (2005).
• 12. Moon D.-O, Kim M.-O, Choi Y.H, Lee H.G, KimN.D. and Kim G.-Y., FEBSLett., 582,3367 (2008).
• 13. Kenar J.A, J. Am. Oil Chem. Soc, 83, 269 (2006).
• 14. Dodou K, Exp. Opin. Invest. New Drug, 14, 1419 (2005).
• 15. Yildirim-Aksoy M, Lim C, Dowd M.K, Wan P.J, Klesius P.H. and Shoemaker C, J. Appl. Microbiol., 97, 87 (2004).
• 16. Kovaci P., Curr. Med Chem., 10, 2711 (2003).
• 17. Brycki B, Brzeziński B, Marciniak B. and Paszyc S, Spectrosc. Lett, 24, 509 (1991).
• 18. Brzeziński B, Marciniak B, Paszyc S. and Zundel G., J. Mol. Struct, 268, 61 (1992).
• 19. Brzeziński B., Olejnik J. and Paszyc S, J. Mol. Struct, 239, 23 (1990).
• 20. Brzeziński B, Rozwadowski Z, Marciniak B. and Paszyc S, J. Mol. Struct, 435, 275 (1997).
• 21. Przybylski P, Wojciechowski G, Brzeziński B, Kozubek H, Marciniak B. and Paszyc S., J. Mol. Struct, 569, 147(2001).
• 22. Ibragimov B.T. and Talipov S.A., J. Incl. Phenomen. Mol. Recogn. Chem., 17, 365 (1994).
• 23. Gdaniec M. and Czajka H, J. Incl. Phenomen. Mol. Recogn. Chem., 22, 187 (1995).
• 24. Dowd M.K. and Stevens E.D., J. Incl. Phenom., 51, 65 (2005).
• 25. Quang T.T., Nguyen K.P.P. and Hansen P.E, Magn. Res. Chem., 43, 302 (2005).
• 26. Dodou K, Anderson R.J, Lough W.J, Small D.A.P, Shelley M.D. and Groundwater P.W, Bioorg. Med. Chem., 13, 4228 (2005).
• 27. Przybylski P, Kira J, Schroeder G., Brzeziński B. and Bartl R, J. Phys. Chem. A, 112, 8061 (2008).
• 28. Przybylski P. and Brzeziński B, Biopolymers (Biospectroscopy), 67, 61 (2002).
• 29. Przybylski P, Schroeder G. and Brzeziński B., Phys. Chem. Chem. Phys., 4, 6137 (2002).
• 30. Przybylski P., Bartl R and Brzeziński B, Biopolymers, 65, 111 (2002).
• 31. Przybylski P., Bejcar G., Huczyński A, Schroeder G, Brzeziński B. and Bartl R, Biopolymers, 82, 521 (2006).
• 32. Przybylski P., Schilf W, Kamieński B, Brzeziński B. and Bartl F.,Magn. Res. Chem.,46,534 (2008).
• 33. Przybylski P, Pyta K, Wicher B, Gdaniec M. and Brzeziński B, J. Mol. Struct., 889, 332 (2008).
• 34. Przybylski P. and Brzeziński B, J. Mol. Struct., 654,167 (2003).
• 35. Przybylski P., Schilf W., Lewandowska W. and Brzeziński B, Biopolymers, 83, 213 (2006).
• 36. Brzeziński B. and Zundel G, Chem. Phys. Lett., 75, 500 (1980).
• 37. Brzeziński B. and Zundel G, J. Chem. Phys., 86, 5135 (1982).
• 38. Zundel G, Mueller A, Ratajczak H., Junge W. and Diemann E, Eds, Electron and Proton Transfer in Chemistry and Biology; Elsevier: Amsterdam, p. 313 (1992).
• 39. Brzeziński B, Paszyc S. and Zundel G, J. Phys. Chem., 167, 7 (1990).
• 40. Adams R, Morris R.C, Geissman T.A., Butterbaugh D.J. and Kirkpatrick K.C., J. Am. Chem. Soc, 60,2193(1938).
• 41. Sheldrick G.M, SHELXS-97. Program for Crystal Structure Solution, University of Goettingen, (1997).
• 42. Sheldrick G.M., SHELXL-97. Program for Crystal Structure Refinement, University of Goettingen, (1997).
• 43. Katrusiak A., J. Mol. Graph. Modelling, 19, 363 (2001).