Synthesis and structure of isocytosine ternary copper(II) complexes[hair space]

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Angel García-Raso, Juan J. Fiol, Bartomeu Adrover, Virtudes Moreno, Elies Molins and Ignasi Mata


Abstract

The ternary complexes (glycylglycinato)(isocytosine)copper(II) dihydrate 1 and (glycylglycinato)(6-methylisocytosine)copper(II) monohydrate 2 have been prepared and characterised by X-ray diffraction, electrochemistry and optical, ESR and IR spectroscopy. The two compounds are slightly distorted square planar, with the four co-ordination sites occupied by the tridentate glycylglycine dianion [O(7), N(13) and N(10)] and N(3) of the pyrimidine base. An additional weak axial interaction exists between an oxygen of a water molecule O(W1) and the copper atom [Cu[hair space][hair space]· · ·[hair space][hair space]O(W1) distances 2.74 and 2.70 Å respectively]. Spectroscopic and electrochemical data are in accord with the crystal structures. Although both compounds exhibit irreversible oxidation processes, the oxidation of CuII to CuIII is best performed with the isocytosine complex.


References

  1. E. J. Baran, Química Bioinorgánica, McGraw-Hill/Interamericana de España, Madrid, 1995 Search PubMed; J. J. R. Fraústo da Silva and R. J. P. Williams, The Biological Chemistry of the Elements. The Inorganic Chemistry of Life, Clarendon Press, Oxford, 1991 Search PubMed; W. Kaim and B. Schwederski, Bioinorganic Chemistry: Inorganic Elements in the Chemistry of Life. An Introduction and Guide, Wiley, Chichester, 1994 Search PubMed.
  2. R. W. Gellert and R. Bau, in Metal Ions in Biological Systems, ed. H. Sigel, Marcel Dekker, New York and Basel, 1979, vol. 8, p. 1 Search PubMed; R. B. Martin and Y. H. Mariam, in Metal Ions in Biological Systems, ed. H. Sigel, Marcel Dekker, New York and Basel, 1979, vol. 8, p. 57 Search PubMed; K. Aoki, in Metal Ions in Biological Systems, ed. H. Sigel, Marcel Dekker, New York and Basel, 1996, vol. 32, p. 91 Search PubMed; M. Sabat, in Metal Ions in Biological Systems, ed. H. Sigel, Marcel Dekker, New York and Basel, 1996, vol. 32, p. 521 Search PubMed; A. Terrón, Comments Inorg. Chem., 1993, 14, 63 Search PubMed.
  3. H. Sigel, (Editor), Metal Ions in Biological Systems, Marcel Dekker, New York and Basel, 1981, vols. 12 and 13 Search PubMed.
  4. (a) G. L. Eichhorn and Y. A. Shin, J. Am. Chem. Soc., 1968, 90, 7323 CrossRef CAS; (b) Y. A. Shin and G. L. Eichhorn, Biochemistry, 1968, 7, 1026 CrossRef CAS; (c) C. Zimmer, G. Luck, H. Fritzsche and H. Triebel, Biopolymers, 1971, 10, 441 CrossRef.
  5. (a) D. J. Szalda, L. G. Marzilli and T. J. Kistenmacher, Biochem. Biophys. Res. Commun., 1975, 63, 601 CAS; (b) T. J. Kistenmacher, D. J. Szalda and L. G. Marzilli, Acta Crystallogr., Sect. B, 1975, 31, 2416 CrossRef; (c) K. Saito, R. Terashima, T. Sakaki and K. Tomita, Biochem. Biophys. Res. Commun., 1974, 61, 83 CrossRef CAS; (d) D. J. Szalda and T. J. Kistenmacher, Acta Crystallogr., Sect. B, 1977, 33, 865 CrossRef.
  6. T. Sakaguchi and M. Janno, J. Chem. Soc. Jpn. C, 1974, 1637 Search PubMed.
  7. T. Matsukawa, S. Ban, K. Sirakawa and M. Yoneda, Yakugaku Zasshi, 1953, 73, 159 Search PubMed.
  8. A. R. Manyak, C. B. Murphy and A. E. Martell, Arch. Biochem. Biophys., 1955, 59, 373 CrossRef CAS.
  9. C. K. Fair, MOLEN, An Interactive Intelligent System for Crystal Structure Analysis, Enraf-Nonius, Delft, 1990.
  10. G. M. Sheldrick, Acta Crystallogr., Sect. A, 1990, 46, 467 CrossRef.
  11. G. M. Sheldrick, SHELXL 93, Program for Crystal Structure Refinement, University of Göttingen, 1993.
  12. A. García-Raso, A. Terrón, J. J. Fiol, E. Molins and C. Miravitlles, Polyhedron, 1995, 14, 2537 CrossRef CAS.
  13. M. M. Stimson and M. J. O'Donnell, J. Am. Chem. Soc., 1952, 74, 1805 CrossRef CAS.
  14. M. Tsuboi, S. Takahasha and I. Harada, Physicochemical Properties of Nucleic Acids, ed. J. Duchesne, Academic Press, London, 1973, vol. 2, p. 91 Search PubMed.
  15. H. Susi, J. S. Ard and J. M. Purcell, Spectrochim. Acta, Part A, 1973, 29, 725 CrossRef CAS.
  16. E. D. Radchenko, G. G. Sheina, N. A. Smorygo and Yu. P. Blagoi, J. Mol. Struct., 1984, 116, 387 CrossRef CAS.
  17. Y. Nishimura and M. Tsuboi, Chem. Phys., 1985, 98, 71 CrossRef CAS.
  18. G. Cervantes, J. J. Fiol, A. Terrón, V. Moreno, J. R. Alabart, M. Aguiló, M. Gómez and X. Solans, Inorg. Chem., 1990, 29, 5168 CrossRef CAS.
  19. K. Nakamoto, Infrared and Raman Spectra of Inorganic and Coordination Compounds, Wiley, New York, 1978p. 243 Search PubMed.
  20. C. J. Simmons, M. Lundeen and K. Seff, Inorg. Chem., 1978, 17, 1429 CrossRef CAS; M. C. Lim, E. Sinn and R. B. Martin, Inorg. Chem., 1976, 15, 807 CrossRef CAS; A. B. P. Lever, Inorganic Electronic Spectroscopy, 2nd edn, Elsevier, New York, 1986 Search PubMed.
  21. W. J. Geary, Coord. Chem. Rev., 1971, 7, 81 CrossRef CAS.
  22. B. A. Goodman and J. B. Raynor, Adv. Inorg. Chem. Radiochem., 1970, 13, 135 Search PubMed; M. Palaniandavar, Y. Somasundaran, M. Lakshminarayanan and H. Manohar, J. Chem. Soc., Dalton Trans., 1996, 1333 RSC; K. R. Justin Thomas, P. Tharmaraj, V. Chandrasekhar, C. D. Bryan and A. W. Cordes, Inorg. Chem., 1994, 33, 5382 CrossRef.
  23. F. P. Bossu, K. L. Chellappa and D. W. Margerum, J. Am. Chem. Soc., 1977, 99, 2195 CrossRef CAS; J. R. Kincaid, J. A. Larrabee and T. G. Spiro, J. Am. Chem. Soc., 1978, 100, 334 CrossRef CAS.
  24. G. A. Hamilton, P. K. Adolf, J. de Jersey, G. C. Dubois, G. R. Dyrkacz and R. D. Libby, J. Am. Chem. Soc., 1978, 100, 1899 CrossRef CAS; G. R. Dyrkacz, R. D. Libby and G. A. Hamilton, J. Am. Chem. Soc., 1976, 98, 626 CrossRef CAS.
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