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Synthesis and Characterization of Monomeric and Dimeric Structures of Calix[4]arenes Containing Amidoferrocene

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Abstract

The reaction of 1,1′-bis(chlorocarbonyl)ferrocene with bis-aminobenzylcalix[4]arene gave amidoferrocene calix[4]arene monomer 1. Compound 1 crystallized in the monoclinic system P21/c with a = 11.196(6) Å, b = 14.971(11) Å, c = 32.007(2) Å, β = 96.413(4)° and V = 5330.9(6) Å3. X-ray diffraction analyses of 1 showed that the calix[4]arene scaffold was in cone conformation in which the intramolecular hydrogen bonding were formed through OH groups at the lower rim to stabilize the structure. Moreover, the intramolecular hydrogen bond between the amide groups of the amidoferrocene unit also presented in the crystal structure. On the other hand, the condensation of 1,1′-bis(chlorocarbonyl)ferrocene with p-tert-bis-aminobenzylcalix[4]arene resulted in the monomeric 2 and [2 + 2] dimeric compounds 3. 1H-NMR studies signified that the calix[4]arene building block in compounds 2 and 3 adopted the cone conformation.

Index Abstract

Synthesis and Characterization of Monomeric and Dimeric Structures of Calix[4]arenes Containing Amidoferrocene

Chomchai Suksai*, Pannee Leeladee, Colin Jennings, Thawatchai Tuntulani*, Palangpon Kongsaeree

The condensation of 1,1′-bis(chlorocarbonyl)ferrocene with p-tert-bis-aminobenzylcalix[4]arene resulted in the monomeric and [2 + 2] dimeric compounds.

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References

  1. Vicens J, Harrowfield J (2007) Calixarenes in the nanoworld. Springer, Dordrecht

    Book  Google Scholar 

  2. Asfari Z, Böhmer V, Harrowfield J, Vicens J (2001) Calixarenes 2001. Kluwer Academic, Dordrecht

    Google Scholar 

  3. Oueslati F, Dumazet-Bonnamour I, Lamartine R (2003) New J Chem 3:644

    Article  Google Scholar 

  4. Banthia S, Samanta A (2005) Org Biomol Chem 18:1428

    Article  Google Scholar 

  5. Chen C-F, Chen Q-Y (2006) New J Chem 2:143

    Article  Google Scholar 

  6. Plenio H, Diodone R (1995) Inorg Chem 34:3964

    Article  CAS  Google Scholar 

  7. Medina JC, Goodnow TT, Bott S, Atwood JL, Kaifer AE, Gokel GW (1991) J Chem Soc Chem Commun 290

  8. Chen Z, Pilgrim AJ, Beer PD (1998) J Electroanal Chem 444:209

    Article  CAS  Google Scholar 

  9. Beer PD, Cadman J (2000) Coord Chem Rev 205:131

    Article  CAS  Google Scholar 

  10. Beer PD, Hayes EJ (2003) Coord Chem Rev 240:167

    CAS  Google Scholar 

  11. Tomapatanaget B, Tuntulani T, Chailapakul O (2003) Org Lett 5:1539

    Article  CAS  Google Scholar 

  12. Suksai C, Leeladee P, Jainuknan D, Tuntulani T, Muangsin N, Chailapakul O, Kongsaeree P, Pakavatchai C (2005) Tetrahedron Lett 46:765

    Article  Google Scholar 

  13. Doorn ARV, Bos M, Harkema S, Eerden JV, Verboom W, Reinhoudt DN (1991) J Org Chem 56:2371

    Article  Google Scholar 

  14. Carr JD, Lambert L, Hibbs DE, Hursthouse MB, Malik KMA, Tucker JHR (1997) Chem Commun 1649

  15. Enraf-Nonius COLLECT. Nonius BV, Delft, The Netherlands, 1997–2000

  16. Otwinowski Z, Minor W (1997) In: Carter CW, Sweet RM (eds) Methods in enzymology, macromolecular crystallography, part A, vol 276. Academic Press, London, pp 307–326

  17. Sheldrick GM (1997) SHELXL-97. University of Gottingen, Gottingen, Germany

    Google Scholar 

  18. Farrugia LJ (1999) J Appl Crystal 32:837

    Article  Google Scholar 

  19. Beer PD, Keefe AD (1990) J Chem Soc Dalton Trans 3675

  20. Brunink JAJ, Verboom W, Engbersen JFJ, Harkema S, Reinhoudt DN (1992) Recl Trav Chim Pays-Bas 111:511

    CAS  Google Scholar 

  21. Böhmer V (1995) Angew Chem Int Ed Engl 34:713

    Article  Google Scholar 

  22. Gutsche CD, Alam I (1988) Tetrahedron 44:4689

    Article  CAS  Google Scholar 

  23. Greenwood NN, Earnshaw A (eds) (1984) Chemistry of the elements. Pergamon, Oxford, p 369

    Google Scholar 

  24. Beer PD, Bernhardt PV (2001) J Chem Soc Dalton Trans 1428

  25. Barišić L, Rapić V, Pritzkow H, Pavlović G, Nemet I (2003) J Organomet Chem 682:131

    Article  Google Scholar 

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Acknowledgements

The financial support from The Thailand Research Fund and the Center of Innovation in Chemistry: Postgraduate Education and Research Program in Chemistry (PERCH-CIC) are gratefully acknowledged. CJ is supported by the NSF-REU Thailand program.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Burapha University, Chonburi, 20131, Thailand

    Chomchai Suksai

  2. Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok, 10330, Thailand

    Pannee Leeladee, Colin Jennings & Thawatchai Tuntulani

  3. Department of Chemistry, Faculty of Science, Mahidol University, Bangkok, 10400, Thailand

    Palangpon Kongsaeree

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  1. Chomchai Suksai
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  2. Pannee Leeladee
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  3. Colin Jennings
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  4. Thawatchai Tuntulani
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  5. Palangpon Kongsaeree
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Correspondence to Chomchai Suksai or Thawatchai Tuntulani.

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Suksai, C., Leeladee, P., Jennings, C. et al. Synthesis and Characterization of Monomeric and Dimeric Structures of Calix[4]arenes Containing Amidoferrocene. J Chem Crystallogr 38, 363–368 (2008). https://doi.org/10.1007/s10870-007-9301-y

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  • DOI: https://doi.org/10.1007/s10870-007-9301-y

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