Ferrocene-Cyclam: A redox-active macrocycle for the complexation of transition metal ions and a study on the influence of the relative permittivity on the coulombic interaction between metal cations

Chemistry - A European Journal

Volumn 7, Issue 13, 2001, Pages 2848-2861

  Plenio, Herbert ^a   Aberle, Clemens ^a   Al Shihadeh, Youseff ^b   Lloris, José Manuel ^b   Martínez Máñez, Ramón ^b   Pardo, Teresa ^b   Soto, Juan ^b  

^a DARMSTADT UNIVERSITY OF TECHNOLOGY   (Germany)

^b UNIVERSITAT POLITÈCNICA DE VALÈNCIA   (Spain)

Author keywords

Coordination chemistry; Electronic communication; Ferrocene; Macrocycles; Redox chemistry

Indexed keywords

ELECTRONS; PERMITTIVITY; POSITIVE IONS; REDOX REACTIONS; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY;

FUOSS ION-PAIRING THEORY;

COMPLEXATION;

COBALT; COPPER; CYCLAM; DIOXANE; FERROCENE; MACROCYCLIC COMPOUND; METAL; NICKEL; WATER; ZINC;

ARTICLE; CHEMICAL REACTION; COMPLEX FORMATION; CRYSTAL STRUCTURE; ELECTRON TRANSPORT; OXIDATION REDUCTION REACTION; X RAY CRYSTALLOGRAPHY;

EID: 0035796421     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20010702)7:13<2848::AID-CHEM2848>3.0.CO;2-P     Document Type: Article

References (81)

1. L. F. Lindoy, The Chemistry of Macrocyclic Ligand Complexes, Cambridge University Press, Melbourne, 1989.
2. J. S. Bradshaw, K. E. Krakowiak, R. M. Izatt, Aza-Crown Macrocycles, Wiley, New York 1993.
3. P. V. Bernhardt, L. A. Jones, Inorg. Chem. 1999, 38, 5086.
4. W. Lee, H. C. Bang, M. P. Suh, J. Mol. Catal. A 2000, 151, 71.
5. G. Dubois, R. J. P. Corriu, C. Reye, S. Brandes, F. Denat, R. Guilard, Chem. Commun. 1999, 2283.
6. M. Teodorescu, K. Matyjaszewski, Macromolecules 1999, 32, 4826.
7. D. J. Szalda, E. Fujita, R. Sanzenbacher, H. Elias, Inorg. Chem. 1994, 33, 4627.
8. P. Caravan, J. J. Ellison, T. J. McMurry, R. B. Lauffer, Chem. Rev. 1999, 99, 2293.
9. C. Nicolas, M. Borel, J. C. Maurizis, J. Labelled Comp. Radiopharm. 2000, 43, 585.
10. T. A. Kaden, Chimia 2000, 54, 46.
11. A. Heppeler, S. Froidevaux, H. R. Macke, E. Jermann, M. Behe, P. Powell, M. Hennig, Chem. Eur. J. 1999, 5, 1974.
12. Y. H. Jang, M. Blanco, S. Dasgupta, D. A. Keire, J. E. Shively, W. A. Goddard, J. Am. Chem. Soc. 1999, 121, 6142.
13. M. E. Padilla-Tosta, J. M. Lloris, R. Martinez-Máñez, A. Benito, J. Soto, T. Pardo, M. A. Miranda, M. D. Marcos, Eur. J. Inorg. Chem. 2000, 741.
14. M. Engeser, L. Fabbrizzi, M. Licchelli, D. Sacchi, Chem. Commun. 1999, 1191.
15. J. M. Lloris, R. Martinez-Máñez, M. E. Padilla-Tosta, T. S. Pardo, J. Soto, P. D. Beer, J. Cadman, D. K. Smith, J. Chem. Soc. Dalton Trans. 1999, 2359.
16. P. D. Beer, Acc. Chem. Res. 1998, 31, 71.
17. M. S. Ram, C. G. Riordan, R. Ostrander, A. L. Rheingold, Inorg. Chem. 1995, 34, 5884.
18. S. Ferguson-Miller, G. T. Babcock, Chem. Rev. 1996, 96, 2889.
19. M. Momenteau, C. A. Reed, Chem. Rev. 1994, 94, 659.
20. V. Amendola, L. Fabbrizzi, M. Licchelli, C. Mangano, P. Pallavicini, L. Parodi, A. Poggi, Coord. Chem. Rev. 1999, 192, 649.
21. P. D. Beer, Adv. Inorg. Chem. 1992, 39, 79.
22. H. Plenio, C. Aberle, Organometallics 1997, 16, 5950.
23. H. Plenio, R. Diodone, J. Organomet. Chem. 1995, 492, 73.
24. H. Plenio, C. Aberle, Angew. Chem. 1998, 110, 1467;
25. Angew. Chem. Int. Ed. 1998, 37, 1397.
26. H. Plenio, D. Burth, Organometallics 1996, 15, 4054.
27. H. Plenio, D. Burth, Organometallics 1996, 15, 1151.
28. F. Le Derf, M. Mazari, N. Mercier, E. Levillain, P. Richomme, J. Becher, J. Garin, J. Orduna, A. Gorgues, M. Salle, Inorg. Chem. 1999, 38, 6096.
29. G. Hennrich, H. Sonnenschein, U. Resch-Genger, Eur. J. Inorg. Chem. 2000, 539.
30. C. Westermeier, H. C. Gallmeier, M. Komma, J. Daub, Chem. Commun. 1999, 2427.
31. T. R. Ward, A. Lutz, S. P. Parel, J. Ensling, P. Gütlich, P. Buglyo, C. Orvig, Inorg. Chem. 1999, 38, 5007.
32. F. Osterloh, W. Saak, D. Haase, S. Pohl, Polyhedron 1999, 18, 1957.
33. P. Forlano, A. R. Parise, J. A. Olabe, Inorg. Chem. 1998, 37, 6406.
34. ox.
35. H. Plenio, J. Yang, R. Diodone, J. Heinze, Inorg. Chem. 1994, 33, 4098.
36. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-144468 (FcCyclam), CCDC-144469 ([Cu(FcCyclam)]), CCDC-144470 ([Zn(FcCyclam)]), and CCDC-144471 ([Co(FcCyclam)]). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+44)1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
37. H. Plenio, R. Diodone, Inorg. Chem. 1995, 34, 3964.
38. To avoid misunderstanding: compared with other chelating ligands, crown ether complexes of alkali metal ions are rather stable; however, compared with the complexes of transition metal ions even with very simple chelating ligands, such as ethylendiamine, the Group 1 metal ion complexes are weak.
39. A. Benito, R. Martínez-Máñez, J. Soto, M. J. L. Tendero, J. Chem. Soc. Farady Trans. 1997, 93, 2175.
40. G. deSantis, L. Fabbrizzi, M. Licchelli, C. Mangano, P. Pallavicini, A. Poggi, Inorg. Chem. 1993, 32, 854.
41. J. M. Lloris, R. Martínez-Máñez, T. Pardo, J. Soto, M. E. Padilla-Tosta, J. Chem. Soc. Dalton Trans. 1998, 2635.
42. M. J. L. Tendero, A. Benito, J. Cano, J. M. Lloris, R. Martínez-Máñez, J. Soto, A. J. Edwards, P. R. Raithby, M. A. Rennie, J. Chem. Soc. Chem. Commun. 1995, 1643.
43. A preliminary report of this work has been published: H. Plenio, C. Aberle, Chem. Commun. 1998, 2697.
44. M. Ciampolini, M. Micheloni, N. Pardi, P. Paoletti, P. Dapporto, F. Zanabi, J. Chem. Soc. Dalton Trans. 1984, 1357.
45. J. Springborg, P. Kofod, C. E. Olsen, I. Sotofte, Acta Chem. Scand. 1995, 49, 564.
46. A. Dumont, V. Jacques, Q. X. Peng, J. F. Desreux, Tetrahedron Lett. 1994, 35, 3707.
47. F. Rabiet, F. Denat, R. Guilard, Synth. Commun. 1997, 27, 979.
48. S. Brandès, F. Denat, S. Lacour, F. Rabiet, F. Barbette, P. Pullumbi, R. Guilard, Eur. J. Org. Chem. 1998, 2349.
49. S. Brandès, C. Gros, F. Denat, P. Pullumbi, R. Guilard, Bull. Soc. Chim. Fr. 1996, 133, 65.
50. F. Denat, S. Brandes, R. Guilard, Synlett. 2000, 5, 561.
51. D. A. Tomalia, L. R. Wilson, United States Patent No. 4,517,122, May 14, 1985
52. [Chem. Abs. 1986, 116, 443329).
53. J. C. Medina, T. T. Goodnow, M. T. Rojas, J. L. Atwood, B. C. Lynn, A. E. Kaifer, G. W. Gokel, J. Am. Chem. Soc. 1992, 114, 10583.
54. H. Elias, Coord. Chem. Rev. 1999, 187, 37.
55. N. G. Connelly, W. E. Geiger, Chem. Rev. 1996, 96, 877.
56. The initial electron transfer is too fast to be monitored by stopped-flow kinetics and is finished in less than 10 ms.
57. C. Aberle, C. Janiak, H. Plenio, unpublished results.
58. R. D. Shannon, Acta Crystallogr. A 1976, 32, 751.
59. M. A. Donelly, M. Zimmer, Inorg. Chem. 1999, 38, 1650 and references therein.
60. J. M. Lloris, R. Martínez-Máñez, T. Pardo, J. Soto, M. E. Padilla-Tosta, J. Chem. Soc. Dalton Trans. 1998, 2635.
61. A. Benito, R. Martínez-Máñez, J. Soto, M. J. L. Tendero, J. Chem. Soc. Faraday Trans. 1997, 93, 2175.
62. R. M. Izatt, K. Pawlak, J. S. Bradshaw, Chem. Rev. 1995, 95, 2529.
63. K. Kodame, E. Kimura, J. Chem. Soc. Chem. Commun. 1975, 891.
64. P. D. Beer, J. Cadman, J. M. Lloris, R. Martínez-Máñez, M. E. Padilla, T. Pardo, D. K. Smith, J. Soto, J. Chem. Soc. Dalton Trans. 1999, 127.
65. A. Ion, I. Ion, A. Popescu, M. Ungureanu, J. Claude Moutet, E. Saint-Aman., Adv. Mater. 1997, 9, 711.
66. R. Martínez-Máñez, J. Soto, J. M. Lloris, T. Pardo, Trends Inorg. Chem. 1998, 5, 183.
67. M. E. Padilla-Tosta, R. Martínez-Máñez, T. Pardo, J. Soto, M. J. L. Tendero, Chem. Commun. 1997, 887.
68. M. S. Skaf, B. M. Ladangi, J. Chem. Phys. 1995, 102, 6542.
69. H. Looyenga, Mol. Phys. 1965, 9, 501.
70. B. Freasier, N. Hamer, D. Isbister, Mol. Phys. 1979, 38, 1661.
71. "Electrical Properties I", Landolt-Börnstein, Properties of Matter in Its Aggregated State, Volume II/6, Springer, Berlin 1959.
72. 2+ distance. This, however, should have no fundamental influence on our interpretation of the changes in ΔE.
73. - anions makes the electric work smaller than when there is no ion-pairing, and, therefore, the electrochemical shift (ΔE) is smaller as ε decreases.
74. J. O. M. Bockris, A. K. N. Reddy, Modern Electrochemistry, Plenum, NY, 1970.
75. 2 + 1051 for solvents with medium to high relative dielectric constants (ranged from ca. 40-75). However, this equation is not adequate for solvents with low permittivity bearing in mind that B should be zero when ε = 1 in agreement with Coulomb's law.
76. For instance anion-cation distances in ion pairs from the Fuoss theory are between 300 and 500 pm for electrolytes such as potassium iodide or potassium bromide.
77. D. D. Perrin, W. L. Armarego, Purification of Laboratory Chemicals, Pergamon, Oxford 1989.
78. M. J. L. Tendero, A. Benito, R. Martínez-Máñez, J. Soto, E. García-España, J. A. Ramirez, M. I. Burguete, S. V. Luis, J. Chem. Soc. Dalton Trans. 1996, 2923.
79. P. Gans, A. Sabatini, A. Vacca, J. Chem. Soc. Dalton Trans. 1985, 1195.
80. V. P. Tverdokhlebov, I. V. Tselinskii, B. V. Gidaspov, G. Y. Chikisheva, J. Org. Chem. 1976, 12, 2268.
81. G. M. Sheldrick, SHELX-97, A Program Suite for the Solution and Refinement of Crystal Structures, University of Göttingen, 1997.