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.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
J.-M. Lehn Angew. Chem. 1988, 100, 91.
(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.
C.J. van Staveren, D.N. Reinhoudt, J. van Eerden, S. Harkema J. Chem. Soc, Chem. Commun. 1987, 974.
C.J. van Staveren, D.N. Reinhoudt, J. van Eerden, S. Harkema J. Chem. Soc, Chem. Commun. 1987, 974.
P. Guerriero, P.A. Vigato, D.E. Fenton, P.C. Hellier Acta Chem. Scand. 1992, 46, 1025.
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.
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.
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.
G. Wilkinson, Ed. “Comprehensive Coordination Chemistry” Pergamon Press, Oxford, 1987.
F.C.J.M. van Veggel, S. Harkema, M. Bos, W. Verboom, G. Klein Woolthuis, D. N. Reinhoudt J. Org. Chem. 1989, 54, 2351.
F.C.J.M. van Veggel, M. Bos, W. Verboom, D. N. Reinhoudt Recl. Trav. Chun. Pays-Bas 1990, 109, 515.
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.
A.R. van Doom, R. Schaafstra, M. Bos, S. Harkema, J. van Eerden, W. Verboom, D. N. Reinhoudt J. Org. Chem. 1991, 56, 6083.
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.
M.J.S. Dewar, E.G. Zoebisch, E.F. Healy, J. J. Stewart J. Am. Chem. Soc. 1985, 107, 3902.
L. Lebioda Acta Crystallogr., Sect B. 1980, B36, 271.
C. Scheringer, D. Mullen, E. Hellner, H.L. Hase, K.-W. Schulte, A. Schweig Acta Crystallogr., Sect B. 1978, B34, 2241.
S. Swaminathan, B.M. Craven, M.A. Spackman, R.F. Stewart Acta Crystallogr., Sect B. 1984, B40, 271.
Similar results were obtained in the range between planar and perpendicular coordination, results are not shown.
A.R. van Doorn, W. Verboom, S. Harkema, D. N. Reinhoudt Synthesis 1992, 119.
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.
A.M. Reichwein, W. Verboom, D. N. Reinhoudt Recl. Trav. Chim. Pays-Bas 1993, 112, 358.
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.
C.J. van Staveren, D.E. Fenton, D.N. Reinhoudt, J. van Eerden, S. Harkema J. Am. Chem. Soc. 1987, 109, 3456.
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.
Emin = -1.00 kcalmol-1 and Rmin = 1.50 Å. Sèe also Y. Marcus, Ion Solvation, Wiley, Chichester, 1985.
G.R. Choppin, L.F. Rao Radiochim. Acta 1984, 37, 143.
Gmelin Handbuch der Anorganischen Chemie, 8th Ed., Uranium supplement Volume E1 and E2, Springer Verlag, Berlin, 1979.
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.
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.
L.C. Groenen and D. N. Reinhoudt in “Supramolecular Chemistry” V. Balzani and L. De Cola (Eds), KLuwer Academic Publishers, Dordrecht, The Netherlands, 1992.
A.M. Reichwein, W. Verboom, S. Harkema, A.L. Spek, D.N. Reinhoudt, manuscript in preparation.
A.R. van Doom, M. Bos, S. Harkema, J. van Eerden, W. Verboom, D. N. Reinhoudt J. Org. Chem. 1991, 56, 2371.
A.R. van Doom, D.J. Rushton, M. Bos, W. Verboom, D. N. Reinhoudt Recl. Trav. Chim. Pays-Bas 1992, 111, 415.
J. Rebek Jr. Angew. Chem. Int. Ed. Engl. 1990, 29, 2445.
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.
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights 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