Metal complexes of 4,11-dimethyl-1,4,8,11-tetraazacyclotetradecane-1, 8bis(methylphosphonic acid) - Thermodynamic and formation/decomplexation kinetic studies

European Journal of Inorganic Chemistry

Volumn , Issue 24, 2009, Pages 3577-3592

  Svobodová, Ivona ^a,b   Havlíčková, Jana ^c   Plutnar, Jan ^c   Lubal, Přemysl ^a   Kotek, Jan ^c   Hermann, Petr ^c  

^a MASARYK UNIVERSITY   (Czech Republic)

^b INSTITUTE OF ANALYTICAL CHEMISTRY   (Czech Republic)

^c CHARLES UNIVERSITY   (Czech Republic)

Author keywords

Copper; Cyclam derivatives; Kinetics; Macrocyclic ligands; Stability constants

Indexed keywords

ACCELERATION; COMPLEXATION; COPPER COMPOUNDS; METAL COMPLEXES; METAL IONS; TRANSITION METALS;

CYCLAM DERIVATIVES; DECOMPLEXATIONS; KINETIC STUDY; MACRO-CYCLIC LIGANDS; METHYLPHOSPHONIC ACID; PENDANT ARMS; SIMPLE APPROACH; SODIUM SALT; STABILITY CONSTANTS; SYNTHESISED;

LIGANDS;

EID: 68649097885     PISSN: 14341948     EISSN: 10990682     Source Type: Journal    
DOI: 10.1002/ejic.200900358     Document Type: Article

References (89)

1. M. Meyer, V. Dahaoui-Ginderey, C. Lecomte, R. Guilard, Coord. Chem. Rev. 1998, 178-180, 1313-1405.
2. L. F. Lindoy, Adv. Inorg. Chem. 1998, 45, 75-125.
3. R. Delgado, V. Félix, L. M. P. Lima, D. W. Price, Dalton Trans. 2007, 2734-2745. ,
4. A. E. Merbach, É. Tóth (Eds.), The Chemistry of Contrast Agents in Medical Magnetic Resonance Imaging, Wiley, Chichester, UK, 2001.
5. Topics in Current Chemistry, Springer, Heidelberg, Germany, 2002, vol. 221.
6. S. Aime, M. Botta, E. Terreno, Adv. Inorg. Chem. 2005, 57, 173-237.
7. P. Caravan, Chem. Soc. Rev. 2006, 35, 512-523.
8. P. Hermann, J Kotek, V. Kubíček, I. Lukeš, Dalton Trans. 2008, 3027-3047.
9. C. J Anderson, M. J Welch, Chem. Rev. 1999, 99, 2219-2234.
10. W.A. Volkert, T.J. Hoffmann, Chem. Rev. 1999, 99, 22692292
11. a) S. Liu, Chem. Soc. Rev. 2004, 33, 445-461;
12. b) S. Liu, D. S. Edwards, Bioconjugate Chem. 2001, 12, 1-34.
13. M. J Welch, C. S. Redvanly (Eds.), Handbook of Radiopharmaceuticals - Radiochemistry and Applications, Wiley, Chichester, UK, 2003.
14. W.P. Li, L. A. Meyer, C. J. Anderson, Top. Curr. Chem. 2005, 252, 179-192.
15. S. V. Smith, .J. Inorg. Biochem. 2004, 98, 1874-1901.
16. X. Sun, C. J Anderson, Methods Enzymol. 2004, 386, 237-261.
17. T. J. Wadas, E. H. Wong, G. R. Weisman, C. J. Anderson, Curr. Pharm. Des. 2007, 13, 3-16.
18. X. Liang, P. J. Sadler, Chem. Soc. Rev. 2004, 33, 246-266.
19. L. A. Bass, M. Wang, M. J. Welch, C. J. Anderson, Bioconjugate Chem. 2000, 11, 527-532.
20. a) E. H. Wong, G. R. Weisman, D. C. Hill, D. P. Reed, M. E. Rogers, J P. Condon, M. A. Fagan, J. C. Calabrese, K.-C. Lam, I. A. Guzei, A. L. Rheingold, J. Am, Chem, Soc. 2000, 122, 10561-10572;
21. b) X. Sun, M. Wuest, G. R. Weisman, E. H. Wong, D. P. Reed, C. A. Boswell, R. J. Motekaitis, A. E. Martell, M. J. Welch, C. J. Anderson, J. Med. Chem. 2002, 45, 469-477
22. c) C. A. Boswell, X. Sun, W Niu, G. R. Weisman, E. H. Wong, A. L. Rheingold, C. J. Anderson, J. Med. Chem. 2004, 47, 1465-1474
23. d) K. S. Woodin, K. J. Heroux, C. A. Boswell, E. H. Wong, G. R. Weisman, W J. Niu, S. A. Tomellini, C. J. Anderson, L. N. Zakharov, A. L. Rheingold, Eur. J. Inorg. Chem. 2005, 4829-4833;
24. e) C. A. Boswell, P. McQuade, G. R. Weisman, E. H. Wong, C. J. Anderson, Nucl. Med. Biol. 2005, 32, 29-38.
25. a) W Niu, E. H. Wong, G. R. Weisman, L. N. Zakharov, C. D. Incarvito, A. L. Rheingold, Polyhedron 2004,23, 1019-1025;
26. b) J E. Sprague, Y. Peng, A. L. Flamengo, K. S. Woodin, E. A. Southwick, G. R. Weisman, E. H. Wong, J A. Golen, A. L. Rheingold, C. J. Anderson, J. Med. Chem. 2007, 50, 25272535
27. K. J. Heroux, K. S. Woodin, D.J. Tranchemontagne, RCB. Widger, E. Southwick, E. H. Wong, G. R. Weisman, S. A. Tomellini, T. J. Wadas, C. J. Anderson, S. Kassel, J. A. Golen, A. L. Rheingold, Dalton Trans. 2007, 2150-2162
28. C. A. Boswell, C. A. S. Regino, K. E. Baidoo, K. J Wong, A. Bumb, H. Xu, D. E. Milenic, J A. Kelley, C. C. Lai, M. W Brechbiel, Bioconjug. Chem. 2008, 19, 1476-1484
29. J. Kotek, P. Vojtíšek, I. Císařová, P. Hermann, P. .Turecka, J. Rohovec, I. Lukeš, Collect, Czech. Chem. Commun. 2000, 65, 1289-13.16.
30. J. Kotek, P. Vojtíšek, I. Císařová, P. Herman, I. Lukeš, Collect, Czech. Chem. Commun. 2001, 66, 363-381.
31. J Kotek, I. Císařová, P. Hermann, I. Lukeš, J Rohovec, Inorg. Chim. Acta 2001, 317, 324-330.
32. a) J. Kotek, P. Lubal, P. Hermann, I. Císařová, I. Lukeš, T Godula, I. Svobodová, P. Táborský, J Havel, Chem. Eur. J. 2003, 9, 233-248;
33. b) P.Lubal, J Maíeček, P. Hermann, J Kotek, J. Havel, Polyhedron 2006, 25, 1884-1892.
34. B. Bosnien, C. K. Poon, M. Tobe, Inorg. Chem. 1965, 4, 11021108.
35. I. Svobodová, P. Lubal, J Plutnar, J Havlíč ková, J Kotek, P. Hermann, I. Lukeš, Dalton Trans. 2006, 5184-5197.
36. I. Svobodová, P. Lubal, P. Hermann, J. Kotek, J. Havel, J. Inclusion Phenom. Macrocycl. Chem. 2004, 49, 11-1
37. I. Svobodová, P. Lubal, P. Hermann, J Kotek, J Havel, Microchim. Acta 2004, 148, 21-26.
38. T. Vitha, J. Kotek, J. Rudovský, V. Kubíček, I. Císařová, P. Hermann, I. Lukeš, Collect. Czech. Chem. Commun, 2006, 71, 337-367.
39. J. Havlíčková, H. Medová, T. Vitha, J. Kotek, I. Císařová, P. Hermann, Dalton Trans. 2008, 5378-5386; and unpublished results.
40. S. Füzerová, J. Kotek, I. Císařová, P. Hermann, K. Binnemans, I. Lukeš, Dalton Trans. 2005, 2908-2915.
41. a) I. M. Helps, D. Parker, J. Chapman, G. Ferguson, J. Chem. Soc, Chem. Commun. 1988, 1094-1.095;
42. b) J. Chapman, G. Ferguson, J. R Gallagher, M. C. Jennings, D. Parker, J. Chem. Soc, Dalton Trans. 1992, 345-353.
43. a) A. Comparone, TA. Kaden, Helv. Chim. Acta 1998, 81, 1765-1772;
44. b) L. Siegfried, A. Comparone, M. Neuburger, T. A. Kaden, Dalton Trans. 2005, 30-36.
45. a) H. Kurosaki, C. Bucher, E. Espinosa, J-M. Barbe, R. Guilard, Inorg. Chim. Acta 2001, 322, 145-149;
46. b) C. Bucher, E. Duval, J-M. Barbe, J-N. Verpeaux, C. Amatore, R. Guilard, C R. Acad. Sci, Ser. Ile Chem. 2000, 3, 211-222.
47. a) A. E. Goeta, J A. K. Howard, D. Maffeo, H. Puschmann, J. A. G. Williams, D. S. Yufit, J. Chem. Soc, Dalton Trans. 2000, 1873-1880;
48. b) A. S. Batsanov, A. E. Goeta, J. A. K. Howard, D. Maffeo, H. Puschmann, J. A. G. Williams, Polyhedron 2001, 20, 981-986.
49. C. Bucher, E. Duval, E. Espinoza, J M. Barbe, J N. Verpeaux, C. Amatore, R. Guilard, Eur. J. Inorg. Chem. 2001, 1077-1079.
50. L. M. P. Lima, R. Delgado, M. G. B. Drew, P. Brandão, V. Félix, Dalton Trans. 2008, 6593-6608.
51. A. W Addison, T. N Rao, J. Reedijk, J. van. Rijn, G. C. Verschoor, J. Chem. Soc., Dalton Trans. 1984, 1349-1356.
52. I. Lukeš, J. Kotek, P. Vojtíšek, P. Hermann, Coord. Chem. Rev. 2001, 216-217, 287-312.
53. R. D. Hancock, R. J. Motekaitis, J. Mashishi, I. Cukrowski, J. H. Reibenspies, A. E. Martell, J. Chem. Soc. Perkin Trans. 2 1996, 1925-1929.
54. a) A. E. Martell, R. M. Smith, Critical Stability Constants, Plenum Press, New York, 1974-1989, vols. 1-6;
55. b) NIST Standard Reference Database 46 (Critically Selected Stability Constants of Metal Complexes), Version 7.0, 2003.
56. a) S. Chaves, R. Delgado, J J. R. Frausto Da Silva, Talanta 1992, 39, 249-254;
57. b) R. Delgado, J. Costa, K.P. Guerra, L. M. P. Lima, Pure Appl. Chem. 2005, 77, 569-579.
58. a) R. Delgado, L. C. Siegfried, T A. Kaden, Heiv. Chim. Acta 1990, 73, 140-148;
59. b) R Marques, L. Gano, M. P. Campello, S. Lacerda, I. Santos, L. M. P. Lima, J. Costa, P. Antunes, R. Delgado, J. Inorg. Biochem. 2006, 100, 270-280.
60. S. A. Pisareva, F. I. Belskii, T. Ya. Medved, M. I. Kabachnik, Izv. Akad. Nauk SSSR, Ser. KMm. 1987, 413-417.
61. S. P. Kasprzyk, R. G. Wilkins, Inorg. Chem. 1982, 21, 3349-3352.
62. R. G. Wilkins, Kinetics and Mechanism of Reactions of Transition Metal Complexes, VCH, Weinheim, 1991.
63. a) F. Cuenot, M. Meyer, E. Espinosa, R. Guilard, Inorg. Chem. 2005, 44, 7895-7910;
64. b) F. Cuenot, M. Meyer, E. Espinosa, A. Bucaille, R. Burgat, R. Guilard, C. Marichal-Westrich, Eur. J. Inorg. Chem. 2008, 267-283.
65. R. Buxtorf, T. A. Kaden, Heiv. Chim. Acta 1974, 57, 1035-1042.
66. N McCann, G. A. Lawrance, Y-M. Neuhold, M. Maeder, Inorg. Chem. 2007, 46, 4002-4009.
67. M. Kodama, E. Kimura, J. Chem. Soc, Dalton Trans. 1977, 1473-1478.
68. M. Maeder, Y-M. Neuhold, G. Puxty, P. King, Phys. Chem, Chem. Phys. 2003, 5, 2836-2841.
69. A. P. Leugger, L. Hertli, T. A. Kaden, Heiv. Chim. Acta 1978, 61, 2296-2306.
70. K.-Y Choi, Polyhedron 1997, 16, 2073-2079.
71. M. Kodama, E. Kimura, J. Chem. Soc., Dalton Trans. 1976, 116-120.
72. M. Kodama, E. Kimura, J. Chem. Soc., Dalton Trans. 1977, 2269-2276.
73. L. Hertli, T. A. Kaden, Heiv. Chim. Acta 1974, 57, 1328-1333.
74. F. A. Dunand, L. Helm, A. E. Merbach, Adv. Inorg. Chem. 2003, 54, 1-69.
75. H. Elias, Coord. Chem. Rev. 1999, 187, 37-73.
76. L.-H. Chen, C-S. Chung, Inorg. Chem. 1988, 27, 1880-1883.
77. G. Royal, V. Dahaoui-Gindrey, S. Dahaoui, A. Tabard, R. Guilard, P. Pulumbi, C. Lecomte, Eur. J. Org. Chem. 1998, 19711975.
78. a) R. Přibil, Analytical Applications of EDTA and Related Compounds, Pergamon Press, Oxford, UK, 1972;
79. b) G. Schwarzen-bach, H. Flaschka, Complexometric Titrations, Methuen, London, UK, 1969.
80. a) Z. Otwinovski, W Minor, HKL Denzo and Scalepack Program Package, Nonius BV, Delft, 1997;
81. b) Z. Otwinovski, W Minor, Methods Enzymol. 1997, 276, 307-326.
82. A. Altomare, M. C. Burla, M. Camalli, G. Cascarano, C. Giacovazzo, A. Guagliardi, G. Polidori, J. Appl. Crystallogr. 1994, 27, 435.
83. G. M. Sheldrick, SHELXL97, Program for Crystal Structure Refinement from Diffraction Data, University of Gottingen, Gottingen, Germany, 1997.
84. a) M. Kývala, I. Lukeš, Chemometrics '95, Abstract book, Pardubice, Czech Republic, 1995, p. 63;
85. b) M. Kývala, P. Lubal, I. Lukeš, IX. Spanish-Italian and Mediterranean Congress on Thermodynamics of Metal Complexes (SIMEC 98), Girona, Spain, 1998. Full version of OPIUM program package is available (free of charge) from http://www.natur.cuni.cz/~kyvala/ opium.html.
86. C. F. Baes Jr, R. E. Mesmer, The Hydrolysis of Cations, Wiley, New York, NY, 1976.
87. Y. Zhang, M. Muhammed, Hvdrometallurgy 2001, 60, 215-236.
88. E. J BiIIo, Excel for Chemists, Wiley-VCH, New York, NY, 2001.
89. Scientist for Windows version 2.01, Micromath Inc., Salt Lake City, UT, 1995.