Skip to main content

Part of the book series: NATO ASI Series ((ASIC,volume 426))

  • 199 Accesses

Abstract

In this review the concept of immobilizing electrophilic centers in synthetic cyclic and acyclic (clefts) receptors will be described. Our first attempts using first-row transition metals did not lead to the desired receptors but resulted in hetero-di- and hetero-trinuclear complexes. The properties will be discussed. The use of the uranyl cation (UO2 2+) gave metallocycles and -clefts which are able to complex both neutral polar molecules as anions. The synthesis, X-ray analysis, and complexation behavior will be discussed. Molecular mechanics calculations have been performed in order to rationalize the results.

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

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 259.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 329.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 329.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. J.-M. Lehn Angew. Chem. 1988, 100, 91.

    Article  CAS  Google Scholar 

  2. (a)V.M.L.J. Aarts, C.J. van Staveren, P.D.J. Grootenhuis, J. van Eerden, L. Kruise, S. Harkema, D.N. Reinhoudt J. Am. Chem. Soc. 1986, 108, 5035; (b) V.M.L.J. Aarts, P.D.J. Grootenhuis, D.N. Reinhoudt, A. Czech, B.P. Czech, R.A. Bartsch Recl.Trav. Chim. Pays-Bas 1988, 107, 94; (c) C.J. van Staveren, V.M.L.J. Aarts, P.D.J. Grootenhuis, J. van Eerden, S. Harkema, D.N. Reinhoudt J. Am. Chem. Soc. 1988, 110, 8134; (d) J. van Eerden, M. Skowronska-Ptasinska, P.D.J. Grootenhuis, S. Harkema, D.N. Reinhoudt J. Am. Chem. Soc. 1989, 111, 700.

    Article  CAS  Google Scholar 

  3. C.J. van Staveren, D.N. Reinhoudt, J. van Eerden, S. Harkema J. Chem. Soc, Chem. Commun. 1987, 974.

    Google Scholar 

  4. C.J. van Staveren, D.N. Reinhoudt, J. van Eerden, S. Harkema J. Chem. Soc, Chem. Commun. 1987, 974.

    Google Scholar 

  5. P. Guerriero, P.A. Vigato, D.E. Fenton, P.C. Hellier Acta Chem. Scand. 1992, 46, 1025.

    Article  CAS  Google Scholar 

  6. F.C.J.M. van Veggel and D. N. Reinhoudt in “Frontiers in Supramolecular Organic Chemistry and Photochemistry”, H.-J. Schneider and H. Dürr (Eds), VCH Verlagsgesellschaft, Weinheim, 1991.

    Google Scholar 

  7. C.J. van Staveren, J. van Eerden, F.C.J.M. van Veggel, S. Harkema, D. N. Reinhoudt J. Am. Chem. Soc. 1988, 110, 4994.

    Article  Google Scholar 

  8. F.C.J.M. van Veggel, S. Harkema, M. Bos, W. Verboom, C.J. van Staveren, G.J. Gerritsma, D. N. Reinhoudt Inorg. Chem. 1989, 28, 1133.

    Article  Google Scholar 

  9. G. Wilkinson, Ed. “Comprehensive Coordination Chemistry” Pergamon Press, Oxford, 1987.

    Google Scholar 

  10. F.C.J.M. van Veggel, S. Harkema, M. Bos, W. Verboom, G. Klein Woolthuis, D. N. Reinhoudt J. Org. Chem. 1989, 54, 2351.

    Google Scholar 

  11. F.C.J.M. van Veggel, M. Bos, W. Verboom, D. N. Reinhoudt Recl. Trav. Chun. Pays-Bas 1990, 109, 515.

    Article  Google Scholar 

  12. F.C.J.M. van Veggel, M. Bos, S. Harkema, H. van de Bovenkamp, W. Verboom, J. Reedijk, D.N. Reinhoudt J. Org. Chem. 1991, 56, 225.

    Article  Google Scholar 

  13. A.R. van Doom, R. Schaafstra, M. Bos, S. Harkema, J. van Eerden, W. Verboom, D. N. Reinhoudt J. Org. Chem. 1991, 56, 6083.

    Article  Google Scholar 

  14. M. Dupuis, D. Spangler, J.J. Wendoloski, NRCC Software Catalog, Vol 1, Program N. QG01 (GAMESS), 1980. M.F. Guest, J. Kendrick, GAMESS Users Manual, Daresbury Laboratory, 1985.

    Google Scholar 

  15. M.J.S. Dewar, E.G. Zoebisch, E.F. Healy, J. J. Stewart J. Am. Chem. Soc. 1985, 107, 3902.

    Article  CAS  Google Scholar 

  16. L. Lebioda Acta Crystallogr., Sect B. 1980, B36, 271.

    Article  Google Scholar 

  17. C. Scheringer, D. Mullen, E. Hellner, H.L. Hase, K.-W. Schulte, A. Schweig Acta Crystallogr., Sect B. 1978, B34, 2241.

    Google Scholar 

  18. S. Swaminathan, B.M. Craven, M.A. Spackman, R.F. Stewart Acta Crystallogr., Sect B. 1984, B40, 271.

    Article  Google Scholar 

  19. Similar results were obtained in the range between planar and perpendicular coordination, results are not shown.

    Google Scholar 

  20. A.R. van Doorn, W. Verboom, S. Harkema, D. N. Reinhoudt Synthesis 1992, 119.

    Google Scholar 

  21. A.R. van Doom, D.J. Rushton, W.F. van Straaten-Nijhuis, W. Verboom, D. N. Reinhoudt Recl. Trav. Chim. Pays-Bas 1992, 111, 421.

    Google Scholar 

  22. A.M. Reichwein, W. Verboom, D. N. Reinhoudt Recl. Trav. Chim. Pays-Bas 1993, 112, 358.

    Article  CAS  Google Scholar 

  23. Quanta/CHARMm package version 2.1A, Molecular Simulations, Waltham, 1989. CHARMM: B.R. Brooks, R.E. Bruccoleri, B.D. Olafson, D.J. States, S. Swaminathan, M. Karplus, J. Comput. Chem. 1983, 4, 187.

    Google Scholar 

  24. C.J. van Staveren, D.E. Fenton, D.N. Reinhoudt, J. van Eerden, S. Harkema J. Am. Chem. Soc. 1987, 109, 3456.

    Article  Google Scholar 

  25. Charges used on the uranyl salophen unit: The charges on U, =O, and O- were fixed at +2.0, 0.0, and -0.9 respectively. The other charges were calculated with the Quanta charge template method.

    Google Scholar 

  26. Emin = -1.00 kcalmol-1 and Rmin = 1.50 Å. Sèe also Y. Marcus, Ion Solvation, Wiley, Chichester, 1985.

    Google Scholar 

  27. G.R. Choppin, L.F. Rao Radiochim. Acta 1984, 37, 143.

    CAS  Google Scholar 

  28. Gmelin Handbuch der Anorganischen Chemie, 8th Ed., Uranium supplement Volume E1 and E2, Springer Verlag, Berlin, 1979.

    Google Scholar 

  29. W.F. Nijhuis, A.R. van Doom, W. Verboom, A.M. Reichwein, F. de Jong, D. N. Reinhoudt J. Am. Chem. Soc. 1991, 113, 3607.

    Article  Google Scholar 

  30. W.F. Nijhuis, A.R. van Doom, W. Verboom, A.M. Reichwein, F. de Jong, D. N. Reinhoudt J. Am. Chem. Soc. 1991, 113, 3607.

    Article  Google Scholar 

  31. L.C. Groenen and D. N. Reinhoudt in “Supramolecular Chemistry” V. Balzani and L. De Cola (Eds), KLuwer Academic Publishers, Dordrecht, The Netherlands, 1992.

    Google Scholar 

  32. A.M. Reichwein, W. Verboom, S. Harkema, A.L. Spek, D.N. Reinhoudt, manuscript in preparation.

    Google Scholar 

  33. A.R. van Doom, M. Bos, S. Harkema, J. van Eerden, W. Verboom, D. N. Reinhoudt J. Org. Chem. 1991, 56, 2371.

    Google Scholar 

  34. A.R. van Doom, D.J. Rushton, M. Bos, W. Verboom, D. N. Reinhoudt Recl. Trav. Chim. Pays-Bas 1992, 111, 415.

    Google Scholar 

  35. J. Rebek Jr. Angew. Chem. Int. Ed. Engl. 1990, 29, 2445.

    Article  Google Scholar 

  36. D.M. Rudkevich, W.P.R.V. Stauthamer, W. Verboom, J.F.J. Engbersen, S. Harkema, D. N. Reinhoudt J. Am. Chem. Soc. 1992, 114, 9671.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 1994 Springer Science+Business Media Dordrecht

About this chapter

Cite this chapter

van Veggel, F.C.J.M., van Hoorn, W.P., Reinhoudt, D.N. (1994). Metallocycles and -Clefts. In: Wipff, G. (eds) Computational Approaches in Supramolecular Chemistry. NATO ASI Series, vol 426. Springer, Dordrecht. https://doi.org/10.1007/978-94-011-1058-7_17

Download citation

  • DOI: https://doi.org/10.1007/978-94-011-1058-7_17

  • Publisher Name: Springer, Dordrecht

  • Print ISBN: 978-94-010-4460-8

  • Online ISBN: 978-94-011-1058-7

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics