Skip to main content
SpringerLink
Log in

X-ray, FT-IR, ESI MS and PM5 studies of Schiff base of gossypol with allylamine and its complexes with alkali metal cations and perchlorate anion

  • Original Research
  • Published:
Structural Chemistry Aims and scope Submit manuscript

Abstract

Crystals of the Schiff base derivative of gossypol with allylamine (GSBAL) were grown and subsequently examined by X-ray diffraction and FT-IR methods. The crystal space group is C2/c with a = 16.057(1) Å, b = 14.112(1) Å, c = 27.185(2) Å, β = 99.371(5)˚ and Z  = 8. In the crystal, GSBAL exists in the enamine–enamine tautomeric form. 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. On the basis of the electrospray ionization mass spectrometry (ESI MS) experiments, it has been shown for the first time that Schiff base of gossypol forms complexes with the perchlorate anion and metal cations simultaneously. The ESI MS spectra of the 1:1:1 mixtures of GSBAL:GOS:M+, in the positive and negative ion detection mode, have indicated the preferential formation of the 1:1 complexes of GSBAL with M+ (Li, Na or K) and ClO4 − over the respective complexes forming between GOS and the metal cation or the anion. The PM5 semiempirical calculations have allowed visualization of the most energetically favourable structures of these two types of GSBAL complexes.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Scheme 2
Fig. 7
Fig. 8
Scheme 3
Scheme 4

Similar content being viewed by others

References

  1. Benedict CR, Liu J, Stipanovic RD (2006) Phytochemistry 67:356. doi:10.1016/j.phytochem.2005.11.015

    Article  CAS  Google Scholar 

  2. Stipanovic RD, Puckhaber LS, Bell AA (2006) J Agric Food Chem 54:1633. doi:10.1021/jf052319e

    Article  CAS  Google Scholar 

  3. Goldsmith KC, Hogarty MD (2005) Cancer Lett 228:133. doi:10.1016/j.canlet.2005.01.048

    Article  CAS  Google Scholar 

  4. Xu L, Yang D, Wang S, Tang W, Liu M, Davis M, Chen J, Rae JM, Lawrence T, Lippman ME (2005) Mol Cancer Ther 4:197

    Article  CAS  Google Scholar 

  5. Kovaci P (2003) Curr Med Chem 10:2711. doi:10.2174/0929867033456369

    Article  Google Scholar 

  6. Olivier CL, Bauer JA, Woher KG (2005) Clin Cancer Res 11:5659

    Google Scholar 

  7. Dodou K (2005) Expert Opin Investig Drugs 14:1419. doi:10.1517/13543784.14.11.1419

    Article  CAS  Google Scholar 

  8. Kenar JA (2006) J Am Oil Chem Soc 83:269. doi:10.1007/s11746-006-1203-1

    Article  CAS  Google Scholar 

  9. Beketov KM, Talipov SA, Ibragimov BT, Praliev KD, Aripov TF (2003) KristallografiyaRuss 48:691

    Google Scholar 

  10. Przybylski P, Ratajczak-Sitarz M, Katrusiak A, Wojciechowski G, Schilf W, Brzezinski B (2003) J Mol Struct 655:293. doi:10.1016/S0022-2860(03)00319-3

    Article  CAS  Google Scholar 

  11. Gdaniec M (1994) J Incl Phenom Macrocycl Chem 17:365. doi:10.1007/BF00707132

    Article  CAS  Google Scholar 

  12. Talipov SA, Ibragimov BT, Izotova LYu, Tilyakov ZG, Dalimov DN (2004) Khim Prir Soedin (Russ.) 40:422

    Google Scholar 

  13. Przybylski P, Bejcar G, Huczyński A, Schroeder G, Brzezinski B, Bartl F (2006) Biopolymers 82:521. doi:10.1002/bip.20505

    Article  CAS  Google Scholar 

  14. Dao V-T, Gaspard C, Mayer M, Werner GH, Nguyen SN, Michelot RJ (2000) Eur J Med Chem 35:805. doi:10.1016/S0223-5234(00)00165-3

    Article  CAS  Google Scholar 

  15. Ziyaev KL, Kamaev FG, Baram NI, Biktimirov L, Ismailov AI (1997) Chem Nat Compd 33:545. doi:10.1007/BF02254801

    Article  CAS  Google Scholar 

  16. Matlin SA, Roshdy S, Cass GB, Freitas CG, Longo RL, Malvestiti I (1990) J Braz Chem Soc 1:128

    CAS  Google Scholar 

  17. Dodou K, Anderson RJ, Lough WJ, Small DAP, Shelley MD, Groundwater PW (2005) Bioorg Med Chem 13:4228. doi:10.1016/j.bmc.2005.04.026

    Article  CAS  Google Scholar 

  18. Przybylski P, Małuszyńska M, Brzezinski B (2005) J Mol Struct 750:152. doi:10.1016/j.molstruc.2005.04.027

    Article  CAS  Google Scholar 

  19. Huczyński A, Stefańska J, Przybylski P, Brzezinski B, Bartl F (2008) Bioorg Med Chem Lett 18:2585. doi:10.1016/j.bmcl.2008.03.038

    Article  CAS  Google Scholar 

  20. Przybylski P, Schilf W, Lewandowska W, Brzezinski B (2006) Biopolymers 83:213. doi:10.1002/bip.20548

    Article  CAS  Google Scholar 

  21. Przybylski P, Brzezinski B, Bartl F (2004) Biopolymers 74:273. doi:10.1002/bip.20075

    Article  CAS  Google Scholar 

  22. Przybylski P, Schroeder G, Brzezinski B (2004) J Mol Struct 699:65. doi:10.1016/j.molstruc.2004.03.056

    Article  CAS  Google Scholar 

  23. Adams R, Morris RC, Geissman TA, Butterbaugh DJ, Kirkpatrick KC (1938) J Am Chem Soc 60:2193. doi:10.1021/ja01276a049

    Article  CAS  Google Scholar 

  24. Sheldrick G (1986) SHELXS-86. Program for crystal structure solution, University of Göttingen

  25. Sheldrick G (1997) SHELXL-97. Program for crystal structure refinement, University of Göttingen

  26. Stewart JJP (2007) Cache Work System Pro Version 7.5.085 UserGuide, Fujitsu, Beaverton, Oregon, USA

  27. Zubatyuk RI, Volovenko YM, Shishkin OV, Gorb L, Leszczynski J (2007) J Org Chem 72:725. doi:10.1021/jo0616411

    Article  CAS  Google Scholar 

  28. Brzezinski B, Olejnik J, Paszc S, Aripov TF (1990) J Mol Struct 220:261. doi:10.1016/0022-2860(90)80116-2

    Article  CAS  Google Scholar 

  29. Przybylski P, Brzezinski B (2002) Biopolymers (Biospectroscopy) 67:61. doi:10.1002/bip.10043

    Article  CAS  Google Scholar 

  30. Sobczyk L, Grabowski SJ, Krygowski TM (2005) Chem Rev 105:3513. doi:10.1021/cr030083c

    Article  CAS  Google Scholar 

  31. Przybylski P, Jasiński K, Brzezinski B, Bartl F (2002) J Mol Struct 611:193. doi:10.1016/S0022-2860(02)00075-3

    Article  CAS  Google Scholar 

Download references

Acknowledgement

Financial assistance of the Polish Ministry of Science and Higher Education–Grant No. N204 056 32/1432 is gratefully acknowledged by P. Przybylski.

Author information

Authors and Affiliations

  1. Faculty of Chemistry, A. Mickiewicz University, Grunwaldzka 6, 60-780, Poznan, Poland

    Piotr Przybylski, Krystian Pyta, Małgorzata Ratajczak-Sitarz, Andrzej Katrusiak & Bogumił Brzezinski

Authors
  1. Piotr Przybylski
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Krystian Pyta
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Małgorzata Ratajczak-Sitarz
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Andrzej Katrusiak
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Bogumił Brzezinski
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Piotr Przybylski.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Przybylski, P., Pyta, K., Ratajczak-Sitarz, M. et al. X-ray, FT-IR, ESI MS and PM5 studies of Schiff base of gossypol with allylamine and its complexes with alkali metal cations and perchlorate anion. Struct Chem 19, 983–995 (2008). https://doi.org/10.1007/s11224-008-9385-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11224-008-9385-9

Keywords

Search

Navigation