Synthesis and metal complexes of aza-macrocycles with pendant arms having additional ligating groups

  • Thomas A. Kaden
Conference paper
Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 121)


In view of new strategies in coordination chemistry macrocycles with functionalized pendant arms represent an interesting class of ligands, which combine both the properties of a macrocyclic structural unit with those of a flexible side-chain to which the functional group is bound. With such systems it is possible to study the effect of axial coordination even for weak ligating groups, since they are brought close to the metal ion, the changes in the properties of the metal ion when the pendant arm becomes coordinated and finally the influence of the metal ion on the reactivity of the functional group.

Since the sterical and geometrical aspects can be kept constant by the macrocycle small effects are expected to be detected. In addition even with a kinetically labile metal ion it is possible to obtain insight into the relation between reactivity and structure.


Metal Complex Nitrile Group Chloroacetic Acid Dimethylamino Group Ligate Group 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

7 References

  1. 1.
    Pedersen, C. J.: J. Am. Chem. Soc. 87, 7017 (1967). For a review see Pedersen, C. J. in “Synthetic Multidentate Macrocyclic Compounds” (Ed. Izatt, R. H., Christensen, J. J.), Academic Press, New York 1978, p. 1CrossRefGoogle Scholar
  2. 2.
    Curtis, N. F.: J. Chem. Soc. 4409 (1960)Google Scholar
  3. 2a.
    Curtis, N. F., House, D. A.: Chem. Ind. 1708 (1961)Google Scholar
  4. 3.
    Busch, D. H.: Helv. Chim. Acta Fasc. Extraordinarius Alfred Werner, 174 (1967)Google Scholar
  5. 3a.
    Curtis, N. F.: Coord. Chem. Rev. 3, 3 (1968)CrossRefGoogle Scholar
  6. 3b.
    Lindoy, L. F., Busch, D. H.: Prep. Inorg. Reactions 6, 1 (1971)Google Scholar
  7. 3c.
    Christensen, J., Eatough, D., Izatt, R.: Chem. Rev. 74, 351 (1974)CrossRefGoogle Scholar
  8. 3d.
    Lindoy, L. F.: Chem. Soc. Rev. 5, 421 (1975)Google Scholar
  9. 3e.
    Newkome, G. R., Sauer, J. D., Roger, J. M., Hager, D. C.: Chem. Rev. 77, 513 (1977)CrossRefGoogle Scholar
  10. 3f.
    Melson, G.: Coordination Chemistry of Macrocyclic Compounds (Ed. Melson, G.), Plenum Press, New York 1979, p. 17Google Scholar
  11. 4.
    Lehn, J. M.: Structure and Bonding 16, 1 (1973)Google Scholar
  12. 5.
    Stetter, H., Frank, W.: Angew. Chem. 88, 760 (1976)Google Scholar
  13. 6.
    Stetter, H., Frank, W., Mertens, R.: Tetrahedron 37, 767 (1981)CrossRefGoogle Scholar
  14. 7.
    Delgado, R., Frausto Dasilva, J. J.: Talanta 29, 815 (1982)CrossRefGoogle Scholar
  15. 8.
    Weitl, F., Raymond, K.: J. Am. Chem. Soc. 101, 2728 (1979)CrossRefGoogle Scholar
  16. 9.
    Muller, F. R., Handel, H.: Tetrahedron Lett. 23, 2769 (1982)CrossRefGoogle Scholar
  17. 10.
    Collman, J. P., Halpert, Th. R., Suslick, K. S.: Metal Ion Activation of Dioxygen (Ed. Spiro, Th. G.), Wiley, New York 1980, p. 1Google Scholar
  18. 11.
    Chang, C. K., Traylor, T. G.: Proc. Nat. Acad. Sc. USA 70, 2647 (1973) and J. Am. Chem. Soc. 95, 5810, 8475, 8477 (1973)Google Scholar
  19. 12.
    Takahashi, M., Takamoto, S.: Bull. Chem. Soc. Japan 50, 3413 (1977)Google Scholar
  20. 13.
    Häfliger, H., Kaden, Th. A.: Hev. Chim. Acta 62, 683 (1979)CrossRefGoogle Scholar
  21. 14.
    Buøen, S., Dale, J., Groth, P., Krane, J.: J. Chem. Soc., Chem. Commun. 1172 (1977)Google Scholar
  22. 15.
    Wainwright, K. P.: J. Chem. Soc. Dalton 2117 (1980)Google Scholar
  23. 16.
    Brown, J. K., Wainwright, K. P.: Abstrac Tu P47, XII ICCC, Budapest 1982 and Abstract P26, Colloque Int. du CNRS: Composé macrocyclique, Strassbourg 1982Google Scholar
  24. 17.
    Siegfried-Hertli, L., Kaden, Th. A.: unpublished resultsGoogle Scholar
  25. 18.
    Schibler, W.: Ph. D. Thesis, Basel 1980Google Scholar
  26. 19.
    Schibler, W., Kaden, Th. A.: J. Chem. Soc., Chem. Commun. 603 (1981)Google Scholar
  27. 20.
    Vitali, P.: Thèse, Strassbourg 1980Google Scholar
  28. 21.
    Louvet, V., Apprion, P., Handel, H.: Tetrahedron Lett. 23, 2245 (1982)CrossRefGoogle Scholar
  29. 22.
    Wagner, F., Barefield, E. K.: Inorg. Chem. 15, 408 (1976)CrossRefGoogle Scholar
  30. 23.
    Stetter, H.: Chem. Ber. 87, 566 (1954)Google Scholar
  31. 23a.
    Dietrich, B., Lehn, J. M., Sauvage, J. P., Blanzat, J.: Tetrahedron 29, 1629 (1973)CrossRefGoogle Scholar
  32. 24.
    Richman, J. E., Atkins, Th. J.: J. Am. Chem. Soc. 96, 2268 (1974)CrossRefGoogle Scholar
  33. 25.
    Lotz, T. J., Kaden, Th. A.: Helv. Chim. Acta 61, 1376 (1978)CrossRefGoogle Scholar
  34. 26.
    Pierpoint, C., Moore, P.: Communication at the Macrocycles Mini-symp., Polytechnic of North London, 1982Google Scholar
  35. 27.
    Furter, P.: Ph. D. Thesis, Basel 1979Google Scholar
  36. 28.
    Hediger, M., Kaden, Th. A.: J. Chem. Soc., Chem. Commun. 14 (1978) and Helv. Chim. Acta 66, 861 (1983)Google Scholar
  37. 29.
    Stöcklin, F.: Ph. D. Thesis, Basel 1981Google Scholar
  38. 30.
    Horner, L., Neumann, H.: Chem. Ber. 98, 3462 (1965)Google Scholar
  39. 31.
    Jäger, E. G.: Z. Chem. 8, 30, 392, 470 (1968)Google Scholar
  40. 31a.
    Wolf, L., Jäger, E. G.: Z. Anorg. Allgem. Chem. 346, 76 (1966)CrossRefGoogle Scholar
  41. 31b.
    Jäger, E. G.: Z. Anorg. Allgem. Chem. 364, 177 (1969)CrossRefGoogle Scholar
  42. 32.
    Tabushi, J., Taniguchi, Y., Kato, H.: Tetrahedron Lett. 1049 (1977)Google Scholar
  43. 33.
    Henrick, H., Tasker, P.: Inorg. Chim. Acta 47, 47 (1980)CrossRefGoogle Scholar
  44. 34.
    Murase, J., Hamada, K., Kida, S.: Inorg. Chim. Acta 54, 471 (1981)CrossRefGoogle Scholar
  45. 35.
    Barefield, E. K., Chueng, D., van Derveer, D., Wagner, F.: J. Chem. Soc., Chem. Commun. 302 (1981)Google Scholar
  46. 36.
    Buttafava, A., Fabbrizzi, L., Perotti, A., Seghi, B.: J. Chem. Soc., Chem. Commun. 1166 (1982)Google Scholar
  47. 37.
    Wieghardt, K., Bossek, U., Chaudhuri, P., Herrmann, W., Menke, B. C., Weiss, J.: Inorg. Chem. 21, 4308 (1982)CrossRefGoogle Scholar
  48. 38.
    Kaden, Th. A.: Coordination Chemistry 20 (Ed. Banerjea, D.), Pergamon Press, Oxford 1980, p. 77Google Scholar
  49. 39.
    Spirlet, M. R., Rebizant, J., Desreux, J. F., Loucin, M. F.: submitted to Acta cryst.Google Scholar
  50. 40.
    Desreux, J. F.: Inorg. Chem. 19, 1319 (1980)CrossRefGoogle Scholar
  51. 41.
    Desreux, J. F., Mercigny, E., Loucin, M. F.: Inorg. Chem. 20, 987 (1981)CrossRefGoogle Scholar
  52. 42.
    Leugger, A. P., Hertli, L., Kaden, Th. A.: Helv. Chim. Acta 61, 2296 (1978)CrossRefGoogle Scholar
  53. 43.
    Hama, H., Takamoto, S.: Nippon Kagaku Kaishi 1182 (1975)Google Scholar
  54. 44.
    Harris, W. R., Raymond, K. M.: J. Am. Chem. Soc. 101, 6534 (1979)CrossRefGoogle Scholar
  55. 44a.
    Harris, W. R., Raymond, K. M., Weitl, F. C.: J. Am. Chem. Soc. 103, 2667 (1981)CrossRefGoogle Scholar
  56. 45.
    Lotz, T. J., Kaden, Th. A.: J. Chem. Soc., Chem. Commun. 15 (1977)Google Scholar
  57. 46.
    Hediger, M.: Ph. D. Thesis, Basel 1979Google Scholar
  58. 47.
    Kim, M. K., Martell, A. E.: J. Coord. Chem. 4, 9 (1974)Google Scholar
  59. 48.
    Billo, E. J.: Inorg. Nucl. Chem. Lett. 10, 613 (1974)CrossRefGoogle Scholar
  60. 48a.
    Kurganov, A., Davankov, V.: Inorg. Nucl. Chem. Lett. 12, 73 (1976)CrossRefGoogle Scholar
  61. 49.
    Kasprzyk, S. P., Wilkins, R. G.: Inorg. Chem. 21, 3349 (1982)CrossRefGoogle Scholar
  62. 50.
    Buckingham, D. A., Clark, C. R., Webley, W. S.: J. Chem. Soc., Chem. Commun. 192 (1981)Google Scholar
  63. 51.
    Kaden, Th. A.: unpublished resultsGoogle Scholar
  64. 52.
    Hediger, M., Schibler, W., Kaden, Th. A.: to be publishedGoogle Scholar
  65. 53.
    Margerum, D. W., Dukes, G. R.: Metal Ions in Biological Systems (Ed. Sigel, H.), Marcel Dekker, New York 1974, Vol. 1, p. 157Google Scholar
  66. 53a.
    Zuberbühler, A. D., Kaden, Th. A.: Helv. Chim. Acta 55, 623 (1972); 57, 1897 (1974); 65, 753 (1982)CrossRefGoogle Scholar
  67. 54.
    Barefield, E. K., Wagner, F.: Inorg. Chem. 12, 2435 (1973)CrossRefGoogle Scholar
  68. 54a.
    Buxtorf, R., Steinmann, W., Kaden, Th. A.: Chimia 28, 15 (1974)Google Scholar
  69. 54b.
    Buxtorf, R., Kaden, Th. A.: Helv. Chim. Acta 57, 1035 (1974)CrossRefGoogle Scholar
  70. 54c.
    D'Aniello, M. J., Mocella, M. T., Wagner, F., Barefield, E K., Paul, I. C.: J. Am. Chem. Soc. 97, 192 (1975)CrossRefGoogle Scholar

Copyright information

© Springer-Verlag 1984

Authors and Affiliations

  • Thomas A. Kaden
    • 1
  1. 1.Institute of Inorganic ChemistryUniversity of BaselBaselSwitzerland

Personalised recommendations