Synthesis and co-ordination chemistry of 1,7-bis(carboxymethyl)-4,10-bis(1-methylimidazol-2-ylmethyl)-1,4,7,10-tetraazacyclododecane

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Massimo Di Vaira, Fabrizio Mani and Piero Stoppioni


Abstract

The potentially octadentate ligand 1,7-bis(carboxymethyl)-4,10-bis(1-methylimidazol-2-ylmethyl)-1,4,7,10-tetraazacyclododecane (H2L), which contains two oxygen and two nitrogen donors on the groups attached to the macrocycle, has been isolated and characterized as the pentahydro-bromide or -perchlorate, H2L·5HY (Y = Br or ClO4). Its co-ordination chemistry towards nickel(II) and zinc(II) ions has been investigated and the structures of the complexes which have been obtained, [NiL]·6.5H2O 1, [Ni(H1.5L)][ClO4]1.5·2H2O 2 and [Zn3L2][ClO4]2·5H2O 3, have been determined by single-crystal X-ray analyses. The metal ion in 1 and 2 is in an approximately octahedral environment formed by the four nitrogen donors of the macrocycle and two donors from the dangling groups, either carboxyl oxygens 1 or methylimidazole nitrogens 2. In the trimetallic zinc complex two metal ions, in peripheral positions, are seven-co-ordinated, whereas the third is tetrahedrally four-co-ordinated.


References

  1. L. F. Lindoy, The Chemistry of Macrocyclic Ligand Complexes, Cambridge University Press, Cambridge, 1989 Search PubMed; R. D. Hancock and A. E. Martell, Chem. Rev., 1989, 89, 1875 Search PubMed; P. V. Bernhardt and G. A. Lawrance, Coord. Chem. Rev., 1990, 104, 297 CrossRef CAS; D. Parker, K. Pulukkody, T. J. Norman, A. Harrison, L. Royle and C. Walker, J. Chem. Soc., Chem. Commun., 1992, 1441 CrossRef CAS; R. Dhillon, A. K. W. Stephens, S. L. Whitbread, S. F. Lincoln and K. P. Wainwright, J. Chem. Soc., Chem. Commun., 1995, 97 RSC.
  2. H. Maumela, R. D. Hancock, L. Carlton, J. H. Reibenspies and K. P. Wainwright, J. Am. Chem. Soc., 1995, 117, 6698 CrossRef CAS.
  3. M. G. B. Drew, Coord. Chem. Rev., 1977, 24, 179 CrossRef CAS; M. Spirlet, J. Rebizant and J. F. Desreux, Inorg. Chem., 1984, 23, 359 CrossRef CAS; I. Murase, I. Ueda, N. Marubayashi, S. Kida, N. Matsumoto, M. Kudo, M. Toyohara, K. Hiate and M. Mikuriya, J. Chem. Soc., Dalton Trans., 1990, 2763 RSC; L. H. Tan, M. R. Taylor, K. P. Wainwright and P. A. Duckworth, J. Chem. Soc., Dalton Trans., 1993, 2921 RSC.
  4. E. Soini, L. Hemmila and P. Dhalen, Ann. Biol. Clin. (Paris), 1990, 48, 567 Search PubMed; R. A. Evangalista, A. Pollak, B. Allore, E. F. Templeton, R. C. Morton and E. P. Diamandis, Clin. Biochem., 1988, 21, 173 CrossRef CAS; E. Lopez, C. Chypre, B. Alpha and G. Mathis, Clin. Chem., 1993, 39, 196 CAS; G. Mathis, Clin. Chem., 1995, 41, 1391 CAS; E. Soini and H. Kojola, Clin. Chem., 1983, 29, 65 CAS; I. Hemmila, V. M. Mukkala and S. Dakubu, Anal. Biochem., 1984, 137, 375 CrossRef; E. F. G. Dickson, A. Pollak and E. P. Diamandis, Photochem. Photobiol., 1995, 27, 3 CrossRef CAS.
  5. V. Alexander, Chem. Rev., 1995, 95, 273 CrossRef CAS; D. Parker, Chem. Soc. Rev., 1990, 19, 271 RSC; D. Parker and K. J. Jankowski, in Andances in Metals in Medicine, eds, M. J. Abrams and B. A. Murrer, Jai Press, New York, 1993, vol. 1, ch. 2, p. 29 Search PubMed.
  6. D. Parker, Chem. Br., 1994, 833 Search PubMed; Comprehensive Supramolecular Chemistry, eds. J. M. Lehn, D. D. Macnicol, J. L. Atwood, J. E. Davies, D. N. Reinhoudt and F. Vogtle, Pergamon, Oxford, 1996, vol. 10, ch. 17 Search PubMed.
  7. S. Aime, M. Botta and G. Ermondi, Inorg. Chem., 1992, 31, 4291 CrossRef CAS; S. Aime, M. Botta, D. Parker and J. A. G. Williams, J. Chem. Soc., Dalton Trans., 1995, 2259 RSC; K. Kumar, T. Jin, X. Wang, J. Desreaux and M. F. Tweedle, Inorg. Chem., 1994, 33, 3823 CrossRef CAS.
  8. K. Kumar, C. A. Chang, L. C. Francesconi, D. D. Dischino, M. F. Malley, J. Z. Gougoutas and M. F. Tweedle, Inorg. Chem., 1994, 33, 3567 CrossRef CAS.
  9. (a) J. F. Desreux, Inorg. Chem., 1980, 19, 1319 CrossRef CAS; (b) X. Wang, T. Jin, V. Comblin, A. Lopez-Mut, E. Merciny and J. F. Desreux, Inorg. Chem., 1992, 31, 1095 CrossRef CAS.
  10. S. Aime, A. S. Batsanov, M. Botta, J. A. K. Howard, D. Parker, K. Senanayake and G. Williams, Inorg. Chem., 1994, 33, 4696 CrossRef CAS; C. J. Broan, K. J. Jankowski, R. Kataky, D. Parker, A. M. Randall and A. Harrison, J. Chem. Soc., Chem. Commun., 1990, 1739 RSC.
  11. J. R. Morrow, S. Amin, C. H. Lake and M. R. Churchill, Inorg. Chem., 1993, 32, 4566 CrossRef CAS; L. Carlton, R. D. Hancock, H. Maumela and K. P. Wainwright, J. Chem. Soc., Chem. Commun., 1994, 1007 RSC; S. Aime, A. Barge, M. Botta, D. Parker and A. S. De Sousa, J. Am. Chem. Soc., 1997, 119, 4767 CrossRef CAS.
  12. P. Pittet, G. S. Laurence, S. F. Lincoln, M. L. Turonek and K. P. Wainwright, J. Chem. Soc., Chem. Commun., 1991, 1205 RSC.
  13. A. K. W. Stephens and S. F. Lincoln, J. Chem. Soc., Dalton Trans., 1993, 2123 RSC.
  14. J. P. L. Cox, K. J. Jankowski, R. Kataky, D. Parker, N. R. A. Beeley, B. A. Boyce, M. A. W. Eaton, K. Millar, A. T. Millican, A. Harrison and C. Walker, J. Chem. Soc., Chem. Commun., 1989, 797 RSC; C. J. Broan, J. P. L. Cox, A. S. Craig, R. Kataky, D. Parker, A. Harrison, A. M. Randall and G. Ferguson, J. Chem. Soc., Perkin Trans. 2, 1991, 87 RSC.
  15. K. Pulukkody, T. J. Norman, D. Parker, L. Royle and C. J. Broan, J. Chem. Soc., Perkin Trans. 2, 1993, 605 RSC.
  16. M. Di Vaira, F. Mani and P. Stoppioni, J. Chem. Soc., Dalton Trans., 1997, 1375 RSC; G. de Martino Norante, M. Di Vaira, F. Mani, S. Mazzi and P. Stoppioni, J. Chem. Soc., Dalton Trans., 1992, 361 RSC; M. Di Vaira, F. Mani, M. Menicatti, P. Stoppioni and A. Vacca, J. Chem. Soc., Dalton Trans., 1997, 661 RSC.
  17. (a) G. de Martino Norante, M. Di Vaira, F. Mani, S. Mazzi and P. Stoppioni, Inorg. Chem., 1990, 29, 2822 CrossRef CAS; (b) M. Di Vaira, F. Mani and P. Stoppioni, J. Chem. Soc., Dalton Trans., 1992, 1127 RSC; (c) M. Di Vaira, B. Cosimelli, F. Mani and P. Stoppioni, J. Chem. Soc., Dalton Trans., 1991, 331 RSC; (d) M. Di Vaira, F. Mani, M. Menicatti, R. Morassi and P. Stoppioni, Polyhedron, 1997, 16, 3585 CrossRef CAS.
  18. M. Di Vaira, F. Mani, N. Nardi, P. Stoppioni and A. Vacca, J. Chem. Soc., Dalton Trans., 1996, 2679 RSC.
  19. N. Walker and D. Stuart, Acta Crystallogr., Sect. A, 1983, 39, 158 CrossRef.
  20. A. Altomare, M. C. Burla, M. Camalli, G. Cascarano, C. Giacovazzo, A. Guagliardi and G. Polidori, SIR 92, J. Appl. Crystallogr., 1994, 27, 435 CrossRef.
  21. G. M. Sheldrick, SHELXL 93, Program for crystal structure refinement, University of Göttingen, 1993.
  22. M. Nardelli, PARST, J. Appl. Crystallogr., 1995, 28, 659 CrossRef CAS.
  23. C. K. Johnson, ORTEP II, Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge, TN, 1976.
  24. H. D. Flack, Acta Crystallogr., Sect. A, 1983, 39, 876 CrossRef.
  25. S. Aime, M. Botta, G. Ermondi, F. Fedeli and F. Uggeri, Inorg. Chem., 1992, 31, 1100 CrossRef CAS; D. D. Dischino, E. J. Delaney, J. E. Emswiler, G. T. Gaughan, J. S. Prasad, S. K. Srivastava and M. F. Tweedle, Inorg. Chem., 1991, 30, 1265 CrossRef CAS.
  26. J. M. Weeks, M. R. Taylor and K. P. Wainwright, J. Chem. Soc., Dalton Trans., 1997, 317 RSC.
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