Synthesis and Structures of Two Triorganotin(IV) Polymers R3Sn{O2CC6H4[N=C(H)}{C(CH3)CH(CH3)-3-OH]-p} n (R = Me and Ph) Containing a 4-[(2Z)-(3-Hydroxy-1-methyl-2-butenylidene)amino] benzoic Acid Framework

  • Tushar S. Basu Baul
  • Cheerfulman Masharing
  • Giuseppe Ruisi
  • Claudio Pettinari
  • Anthony Linden


Two new polymeric triorganotin(IV) complexes R3Sn{O2CC6H4[N=C(H)}{C(CH3)CH(CH3)-3-OH]-p} n ([Me3Sn(LH)] n : 1) and ([Ph3Sn(LH)] n : 2) containing a 4-[(2Z)-(3-hydroxy-1-methyl-2-butenylidene)amino]benzoate (LH) framework were prepared. Both compounds have been characterized by 1H, 13C, 119Sn NMR, IR and 119Sn Mössbauer spectroscopic techniques in combination with elemental analyses. The crystal structures of complexes 1 and 2 reveal that they exist as polymeric zig-zag chains in which the LH-bridged Sn-atoms adopt a trans-R3SnO2 trigonal bipyramidal configuration with R groups in the equatorial positions and the axial sites occupied by an oxygen atom from the carboxylate ligand and the alcoholic oxygen atom of the next carboxylate ligand in the chain. The carboxylate ligands coordinate in the zwitterionic form with the alcoholic proton moved to the nearby nitrogen atom.


Organometallic polymers Triorganotin carboxylates 4-[(2Z)-(3-Hydroxy-1-methyl-2-butenylidene)amino]benzoate NMR Mössbauer Crystal structure 



The financial support of the Department of Science & Technology, New Delhi, India (Grant No. SR/S1/IC-03/2005, TSBB) and the University Grants Commission, New Delhi, India through SAP-DSA, Phase-III are gratefully acknowledged. GR is indebted to the Università di Palermo, Italy for financial support. Dr. David Wolstenholme, Dalhousie University, Canada is thanked for assistance with the crystal structure determination of compound 1.


  1. 1.
    A.J. Crowe, P.J. Smith, C.J. Cardin, H.E. Parge, F.E. Smith, Cancer Lett. 24, 45 (1984)CrossRefGoogle Scholar
  2. 2.
    F. Huber, G. Roge, L. Carl, G. Atassi, F. Spreafico, S. Filippeschi, R. Barbieri, A. Silvestri, E. Rivarola, G. Ruisi, F. Di Bianca, G. Alonzo, J. Chem. Soc. Dalton Trans. 523 (1985)Google Scholar
  3. 3.
    M. Gielen, Coord. Chem. Rev. 151, 41 (1996)Google Scholar
  4. 4.
    M. Gielen, E.R.T. Tiekink, in Metallotherapeutic Drug and Metal-based Diagnostic Agents: 50 Sn Tin Compounds and Their Therapeutic Potential, ed. by M. Gielen, E.R.T. Tiekink (Wiley, 2005), pp. 421–439Google Scholar
  5. 5.
    S.R. Collinson, D.E. Fenton, Coord. Chem. Rev. 148, 19 (1996)CrossRefGoogle Scholar
  6. 6.
    S.G. Teoh, G.Y. Yeap, C.C. Loh, L.W. Foong, S.B. Teo, H.K. Fun, Polyhedron 16, 2213 (1997)CrossRefGoogle Scholar
  7. 7.
    C. Pettinari, F. Marchetti, R. Pettinari, D. Martini, A. Drozdov, S. Troyanov, Inorg. Chim. Acta 325, 103 (2001)CrossRefGoogle Scholar
  8. 8.
    T.S. Basu Baul, S. Dutta, E. Rivarola, M. Scopelliti, S. Choudhuri, Appl. Organomet. Chem. 15, 947 (2001)CrossRefGoogle Scholar
  9. 9.
    P. Cardiano, O. Giuffre, L. Pellerito, A. Pettignano, S. Sammartano, M. Scopelliti, Appl. Organomet. Chem. 20, 425 (2006)CrossRefGoogle Scholar
  10. 10.
    D. Dakternieks, T.S. Basu Baul, S. Dutta, E.R.T. Tiekink, Organometallics 17, 3058 (1998)CrossRefGoogle Scholar
  11. 11.
    T.S. Basu Baul, E.R.T. Tiekink, Z. Kristallogr, NCS 214, 361 (1999)Google Scholar
  12. 12.
    T.S. Basu Baul, S. Dutta, E. Rivarola, R. Butcher, F.E. Smith, J. Organomet. Chem. 654, 100 (2002)CrossRefGoogle Scholar
  13. 13.
    T.S. Basu Baul, S. Dutta, C. Masharing, E. Rivarola, U. Englert, Heteroat. Chem. 14, 149 (2003)CrossRefGoogle Scholar
  14. 14.
    T.S. Basu Baul, C. Masharing, R. Willem, M. Biesemans, M. Holčapek, R. Jirásko, A. Linden, J. Organomet. Chem. 690, 3080 (2005)CrossRefGoogle Scholar
  15. 15.
    A. Linden, T.S. Basu Baul, C. Masharing, Acta Crystallogr. E 61, m557 (2005)CrossRefGoogle Scholar
  16. 16.
    T.S. Basu Baul, C. Masharing, S. Basu, E. Rivarola, M. Holčapek, R. Jirásko, A. Lyčka, D. de Vos, A. Linden, J. Organomet. Chem. 691, 952 (2006)CrossRefGoogle Scholar
  17. 17.
    T.S. Basu Baul, C. Masharing, G. Ruisi, R. Jirásko, M. Holčapek, D. de Vos, D. Wolstenholme, A. Linden, J. Organomet. Chem. 692, 4849 (2007)CrossRefGoogle Scholar
  18. 18.
    T.S. Basu Baul, C. Masharing, E. Rivarola, F.E. Smith, R. Butcher, Struct. Chem. 18, 231 (2007)CrossRefGoogle Scholar
  19. 19.
    T.S. Basu Baul, C. Masharing, S. Basu, C. Pettinari, E. Rivarola, S. Chantrapromma, H.K. Fun, Appl. Organomet. Chem. 22, 114 (2008)CrossRefGoogle Scholar
  20. 20.
    R. Hooft, KappaCCD Collect Software (Nonius BV, Delft, 1999)Google Scholar
  21. 21.
    Z. Otwinowski, W. Minor, in Methods in Enzymology, vol. 276, Macromolecular Crystallography, Part A, ed. by C.W. Carter Jr., R.M. Sweet (Academic Press, New York, 1997), pp. 307–326Google Scholar
  22. 22.
    R.H. Blessing, Acta Crystallogr. A 51, 33 (1995)CrossRefGoogle Scholar
  23. 23.
    A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, M.C. Burla, G. Polidori, M. Camalli, sir92 J. Appl. Crystallogr. 27, 435 (1994)Google Scholar
  24. 24.
    P.T. Beurskens, G. Admiraal, G. Beurskens, W.P. Bosman, S. Garcia-Granda, R.O. Gould, J.M.M. Smits, C. Smykalla, PATTY: The DIRDIF Program System, Technical Report of the Crystallography Laboratory (University of Nijmegen, Nijmegen, 1992)Google Scholar
  25. 25.
    P.T. Beurskens, G. Admiraal, G. Beurskens, W.P. Bosman, R. de Gelder, R. Israel, J.M.M. Smits, DIRDIF94: The DIRDIF Program System, Technical Report of the Crystallography Laboratory (University of Nijmegen, Nijmegen, 1994)Google Scholar
  26. 26.
    G.M. Sheldrick, SHELXL97, Program for the Refinement of Crystal Structures (University of Göttingen, Göttingen, 1997)Google Scholar
  27. 27.
    T.S. Basu Baul, S. Basu, D. De Vos, A. Linden, Invest. New Drugs (2009). doi: 10.1007/s10637-008-9189-1 (in press)
  28. 28.
    J. Bernstein, R.E. Davis, L. Shimoni, N.-L. Chang, Angew. Chem. Int. Ed. Engl. 34, 1555 (1995)CrossRefGoogle Scholar
  29. 29.
    R. Barbieri, F. Huber, L. Pellerito, G. Ruisi, A. Silvestri, in Chemistry of Tin: 119 Sn Mössbauer Studies on Tin Compounds, ed. by P.J. Smith (Blackie, London, 1998), pp. 496–540Google Scholar
  30. 30.
    G.M. Bancroft, R.H. Platt, Adv. Inorg. Chem. Radiochem. 15, 59 (1972)Google Scholar
  31. 31.
    J. Holeček, M. Nádvorník, K. Handliř, A. Lyčka, J. Organomet. Chem. 241, 177 (1983)CrossRefGoogle Scholar
  32. 32.
    R. Willem, I. Verbruggen, M. Gielen, M. Biesemans, B. Mahieu, T.S. Basu Baul, E.R.T. Tiekink, Organometallics 17, 5758 (1998)CrossRefGoogle Scholar
  33. 33.
    F. Marchetti, C. Pettinari, A. Cingolani, G. Gioia Lobbia, A. Cassetta, L. Barba, J. Organomet. Chem. 517, 141 (1996)CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC 2009

Authors and Affiliations

  • Tushar S. Basu Baul
    • 1
  • Cheerfulman Masharing
    • 1
  • Giuseppe Ruisi
    • 2
  • Claudio Pettinari
    • 3
  • Anthony Linden
    • 4
  1. 1.Department of ChemistryNorth-Eastern Hill UniversityShillongIndia
  2. 2.Dipartimento di Chimica Inorganica e Analitica “Stanislao Cannizzaro”Università di PalermoPalermoItaly
  3. 3.Dipartimento di Scienze ChimicheUniversità di CamerinoCamerinoItaly
  4. 4.Institute of Organic ChemistryUniversity of ZurichZurichSwitzerland

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