Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Preparation and Properties of New Di-N-alkylated 14-Membered Tetraaza Macrocycles and Their Nickel(II) and Copper(II) Complexes

  • Published : 20001100
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Abstract

New 14-membered tetraaza macrocycles 1,8-diallyl-3,5,7,7,10,12,14,14-octamethyl-1,4,8,11-tetraazacyclotetradecane $(L^2)$ and 1,8-bis(n-propyl)-3,5,7,7,10,12,14,14-octamethyl-1,4,8,11-tetraazacyclotetradecane $(L^3)$ have been prepared by direct react ion of 2,5,5,7,9,12,12,14-octamethyl-1,4,8,11-tetraazacyclotetradecane $(L^1)with$ allyl bromide or n-propyl bromide. The nickel(II) and copper(II) complexes of $L^2andL^3have$ been prepared. The macrocycles show high copper(II) selectivity against nickel(II) ion in methanol solutions containing water. The wavelengths (ca. 505 nm) of the d-d bands for the nickel(II) complexes are extraordinarily longer than those for the complexes of $L^1and$ other related di-N-alkylated 14-membered tetraaza macrocycles. Crystal structure of $[NiL^2](ClO4)_2$ shows that the average Ni-N bond distance $(1.992\AA)$ of the complex is distinctly longer than those of other related nickel(II) complexes. Effects of the N- and C-substituents on the properties of the macrocyclic compounds are discussed.

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References

  1. J. Am. Chem. Soc. v.112 Weisman, G. R.;Rogers, M. E.;Wong, E. S.;Jasinski, J. P.;Paight, E. S.
  2. Acta Chemica Scand. v.49 Springborg, J.;Olsen, C. E.;SØtofte, I.
  3. J. Chem. Soc., Dalton Trans. Zilbermann, I.;Golub, G.;Cohen, H.;Meystein, D.
  4. Inorg. Chim. Acta v.246 Oberholer, M. R.;Siegfried, L. C.;Kaden, T. A.
  5. Inorg. Chim. Acta v.255 Golub, G.;Lashaz, A.;Cohen, H.;Paoletti, P.;Bencini, A.;Valtancoli, B.;Meyerstein, D.
  6. J. Chem. Soc., Chem. Commun. Golub, G.;Cohen, H.;Meyerstein, D.
  7. Inorg. Chem. v.24 Jubran, N.;Ginzburg, G.;Cohen, H.;Koresh, Y.;Meyerstein, D.
  8. Inorg. Chem. v.31 Ropper, J. R.;Elias, H.
  9. Inorg. Chem. v.23 Klaehn, D.-D.;Paulus, H.;Grewe, R.;Elias, H.
  10. Inorg. Chem. v.22 Nakani, B. S.;Welsh, J. J. B.;Hancock, R. D.
  11. Inorg. Chem. v.23 Madeyski, C. M.;Michael, J. P.;Hancock, R. D.
  12. Bull. Korean Chem. Soc. v.13 Kang, S.-G.;Kweon, J. K.;Jung, S.-K.;Kim, M.-S.
  13. Bull. Korean Chem. Soc. v.14 Kang, S.-G.;Kim, M.-S.;Choi, J.-S.;Cho, M. H.
  14. Polyhedron v.14 Kang, S.-G.;Kim, M.-S.;Choi, J.-S.;Cho, M. H.
  15. Inorg. Chem. v.15 Wagner, F.;Barefield, E. K.
  16. Inorg. Chem. v.12 Barefield, E. K.;Wagner, F.
  17. J. Chem. Soc., Dalton Trans. Chapman, J.;Ferguson, G.;Gallagher, J. F.;Jennings, M. C.;Parker, D.
  18. Inorg. Chem. v.25 Barefield, E. K.;Freeman, G. M.;Derveer, D. G. V.
  19. Bull. Korean Chem. Soc. v.13 Kang, S.-G.;Kweon, J. K.
  20. Inorg. Chim. Acta v.279 Kang, S.-G.;Kim, M.-S.;Whang, D.;Kim, K.
  21. Kang, S.-G.;Song, J.
  22. Bull. Chem. Soc. v.62 Bembi, R.;Sondhi, S. M.;Singh, A. K.;Jhanji, A. K.;Roy, T. G.;Lown, J. W.;Ball, R. G.
  23. J. Am. Chem. Soc. v.95 Ito, T.;Busch, D. H.
  24. Determination and Use of Stability Constants, 2nd Ed. Martell. A. E.;Motekaitis, R.
  25. J. Chem. Soc., Dalton Trans. Luckay, R. C.;Hancock, R. D.
  26. Inorg. Chem. v.24 Thom, V. J.;Hosken, G. D.;Hancock, R. D.
  27. SHELXS-86 User Guide Crystallography Department Sheldrick, G. M.
  28. SHELXL-93 User Guide Crystallography Department Sheldrick, G. M.
  29. J. Appl. Cryst. v.28 Parkin, S.;Moezzi, B.;Hope, H.
  30. Inorg. Chem. v.31 Bakak, A.;Espension, J. H.
  31. Inorg. Chem. v.24 Jubran, N.;Ginzburg, G.;Cohen, H.;Koresh, Y.;Meyerstein, D.
  32. Coordination Chemistry in Macrocyclic Compounds; ed. Urbach, F. L.
  33. Bull. Korean Chem. Soc. v.12 Kang, S.-G.;Kweon, J. K.;Jung, S.-K.
  34. J. Chem. Soc., Dalton Trans. Hay, R.W.;Piplani, D. P.
  35. Inorg. Chem. v.15 Haltman, M. S.;Cumming, S. C.
  36. J. Chem. Soc., Dalton Trans. Hambley, T.
  37. Mechanisms of Inorganic Reactions, 2nd ed Basolo, F.;Pearson, R. G.
  38. Inorganic Chemistry: Principles of Structure and Reactivity, 4th ed Huheey, J. E.;Keiter, E. A.;Keiter, R. L.

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