Synthesis, characterization, and X-ray crystal structures of cyclam derivatives. 5. Copper(II) binding studies of a pyridine-strapped 5,12-dioxocyclam-based macrobicycle

Inorganic Chemistry

Volumn 43, Issue 18, 2004, Pages 5572-5587

  Meyer, Michel ^a   Frémond, Laurent ^a   Espinosa, Enrique ^a   Guilard, Roger ^a   Ou, Zhongping ^b   Kadish, Karl M ^b  

^a UNIVERSITÉ DE BOURGOGNE   (France)

^b University of Houston   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,4,8,11 TETRAAZACYCLOTETRACECANE 5,12 DIONE; 1,9,12,18,22 PENTAAZATRICYCLO[7.6.6.1]DOCOSA 3,5,7 (22) TRIENE 13,19 DIONE; 5,12 DIOXOCYCLAM; AMIDE; BASE; COORDINATION COMPOUND; COPPER; COPPER COMPLEX; CYCLAM DERIVATIVE; DIOXOCYCLAM; FUNCTIONAL GROUP; MACROBICYCLIC COMPOUND; MACROCYCLIC COMPOUND; METHANOL; PYRIDINE; PYRIDINE DERIVATIVE; RECEPTOR; UNCLASSIFIED DRUG;

ACIDITY; AQUEOUS SOLUTION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; CRYSTAL STRUCTURE; CYCLIC POTENTIOMETRY; DEPROTONATION; DISSOCIATION; ELECTROCHEMICAL ANALYSIS; ELECTRON SPIN RESONANCE; GEOMETRY; INFRARED SPECTROSCOPY; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; METAL BINDING; POTENTIOMETRY; PROTON TRANSPORT; SPECTROELECTROCHEMICAL ANALYSIS; STEREOCHEMISTRY; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY; X RAY DIFFRACTION;

COPPER; CRYSTALLOGRAPHY, X-RAY; HETEROCYCLIC COMPOUNDS; LACTAMS, MACROCYCLIC; MODELS, CHEMICAL; ORGANOMETALLIC COMPOUNDS; PYRIDINES;

EID: 4444308541     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic049518k     Document Type: Article

References (105)

1. For the previous paper in this series, see: Frémond, L.; Espinosa, E.; Meyer, M.; Denat, F.; Guilard, R.; Huch, V.; Veith, M. New J. Chem. 2000, 24, 959.
2. Alder, R. W. Chem. Rev. 1989, 89, 1215.
3. Alder, R. W. Tetrahedron 1990, 46, 683.
4. Dietrich, B.; Viout, P.; Lehn, J. M. Macrocyclic Chemistry; VCH: Weinheim, Germany, 1993.
5. Nelson, J.; McKee, V.; Morgan, G. Prog. Inorg. Chem. 1998, 47, 167.
6. Bencini, A.; Bianchi, A.; Garcia-Espana, E.; Micheloni, M.; Ramirez, J. A. Coord. Chem. Rev. 1999, 188, 97.
7. Ingham, A.; Rodopoulos, M.; Coulter, K.; Rodopoulos, T.; Subramanian, S.; McAuley, A. Coord. Chem. Rev. 2002, 233-234, 255.
8. Hubin, T. J. Coord. Chem. Rev. 2003, 241, 27.
9. Springborg, J. Dalton Trans. 2003, 1653.
10. Virta, P.; Lönnberg, H. J. Org. Chem. 2003, 68, 8534.
11. Kimura, E. J. Coord. Chem. 1986, 15, 1.
12. Sigel, H.; Martin, R. B. Chem. Rev. 1982, 82, 385.
13. Denat, F.; Brandès, S.; Guilard, R. Synlett 2000, 561.
14. Tomalia, D. A.; Wilson, L. R. U.S. Patent 4 517 122, 1985.
15. Betschart, C.; Hegedus, L. S. J. Am. Chem. Soc. 1992, 114, 5010.
16. Hegedus, L. S.; Moser, W. H. J. Org. Chem. 1994, 59, 7779.
17. Hsiao, Y.; Hegedus, L. S. J. Org. Chem. 1997, 62, 3586.
18. Hegedus, L. S.; Greenberg, M. M.; Wendung, J. J.; Bullock, J. P. J. Org. Chem. 2003, 68, 4179.
19. Frémond, L. Ph.D. Thesis, Université de Bourgogne, Dijon, France, 2002.
20. Gavrish, S. P.; Lampeka, Y. D.; Lightfoot, P. Inorg. Chim. Acta 2004, 357, 1023.
21. Goeta, A. E.; Howard, J. A. K.; Maffeo, D.; Puschmann, H.; Williams, J. A. G.; Yufit, D. S. J. Chem. Soc., Dalton Trans. 2000, 1873.
22. Denat, F.; Lacour, S.; Brandès, S.; Guilard, R. Tetrahedron Lett. 1997, 38, 4417.
23. Brandès, S.; Denat, F.; Lacour, S.; Rabiet, F.; Barbette, F.; Pullumbi, P.; Guilard, R. Eur. J. Org. Chem. 1998, 2349.
24. Plenio, H.; Aberle, C. Chem. Commun. 1998, 2697.
25. Plenio, H.; Aberle, C.; Shihadeh, Y. A.; Lions, J. M.; Martinez-Manez, R.; Pardo, T.; Soto, J. Chem.-Eur. J. 2001, 7, 2848.
26. Hubin, T. J.; Tyryshkin, N.; Alcock, N. W.; Busch, D. H. Acta Crystallogr., Sect. C 1999, 55, 1888.
27. Dumas, S.; Lastra, E.; Hegedus, L. S. J. Am. Chem. Soc. 1995, 117, 3368.
28. Kuester, E.; Hegedus, L. S. Organometallics 1999, 18, 5318.
29. Puntener, K.; Hellman, M. D.; Kuester, E.; Hegedus, L. S. J. Org. Chem. 2000, 65, 8301.
30. Wynn, T.; Hegedus, L. S. J. Am. Chem. Soc. 2000, 122, 5034.
31. Brugel, T. A.; Hegedus, L. S. J. Org. Chem. 2003, 68, 8409.
32. Hegedus, L. S.; Sundermann, M. J.; Dorhout, P. K. Inorg. Chem. 2003, 42, 4346.
33. Achmatowicz, M.; Hegedus, L. S.; David, S. J. Org. Chem. 2003, 68, 7661.
34. Johnston, D. H.; Shriver, D. F. Inorg. Chem. 1993, 32, 1045.
35. Nakamoto, K. Infrared and Roman Spectra of Inorganic and Coordination Compounds; Wiley: New York, 1970.
36. Kimura, E.; Koike, T.; Machida, R.; Nagai, R.; Kodama, M. Inorg. Chem. 1984, 23, 4181.
37. Siegfried, L.; Neuburger, M.; Zehnder, M.; Kaden, T. A. J. Chem. Soc., Chem. Commun. 1994, 951.
38. Costa, J.; Delgado, R.; Drew, M. G. B.; Félix, V.; Saint-Maurice, A. J. Chem. Soc., Dalton Trans. 2000, 1907.
39. Cremer, D.; Pople, J. A. J. Am. Chem. Soc. 1975, 97, 1354.
40. Félix, V.; Costa, J.; Delgado, R.; Drew, M. G. B.; Duarte, M. T.; Resende, C. J. Chem. Soc., Dalton Trans. 2001, 1462.
41. Murakami, Y.; Matsuda, Y.; Sakata, K. Inorg. Chem. 1971, 10, 1728.
42. Bellamy, L. J. The Infrared Spectra of Complex Molecules, 3rd ed.; Chapman and Hall: London, 1975; Vol. 1.
43. Bellamy, L. J. The Infrared Spectra of Complex Molecules. Advances in Infrared Group Frequencies, 2nd ed.; Chapman and Hall: London, 1980; Vol. 2.
44. Silverstein, R. M.; Bassler, G. C.; Morrill, T. C. Spectrometric Identification of Organic Compounds, 5th ed.; John Wiley and Sons: New York, 1991.
45. Kim, M. K.; Martell, A. E. Biochemistry 1964, 3, 1170.
46. Kim, M. K.; Martell, A. E. J. Am. Chem. Soc. 1966, 88, 914.
47. Pagenkopf, G. K.; Margerum, D. W. J. Am. Chem. Soc. 1968, 90, 6963.
48. Brunetti, A. P.; Lim, M. C.; Nancollas, G. H. J. Am. Chem. Soc. 1968, 90, 5120.
49. Martell, A. E.; Kim, M. K. J. Coord. Chem. 1974, 4, 9.
50. The Cambridge Structural Database, release 5.24; Cambridge Structural Database: Cambridge, U.K., 2002.
51. Alien, F. H. Acta Crystallogr., Sect. B 2002, 58, 380.
52. Alien, F. H.; Motherwell, W. D. S. Acta Crystallogr., Sect. B 2002, 58, 407.
53. Beveridge, K. A.; McAuley, A.; Xu, C. Inorg. Chem. 1991, 30, 2074.
54. Zhu, S.; Kou, F.; Lin, C.; Lin, M.; Chen, Y. Inorg. Chem. 1996, 35, 5851.
55. Kepert, D. L. Inorganic Stereochemistry; Springer-Verlag: Heidelberg, Germany, 1982; Vol. 6.
56. Addison, A. W.; Rao, T. N.; Reedijk, J.; Van Rijn, J.; Verschoor, G. C. J. Chem. Soc., Dalton Trans. 1984, 1349.
57. Lever, A. B. P. Inorganic Electronic Spectroscopy, 2nd ed.; Elsevier: Amsterdam, 1984.
58. Amundsen, A. R.; Whelan, J.; Bosnich, B. J. Am. Chem. Soc. 1977, 99, 6730.
59. Solomon, E. I.; Hare, J. W.; Gray, H. B. Proc. Natl. Acad. Sci. U.S.A. 1976, 73, 1389.
60. Lampeka, Y. D.; Gavrish, S. P. Polyhedron 2000, 19, 2533.
61. Prenesti, E.; Daniele, P. G.; Prencipe, M.; Ostacoli, G. Polyhedron 1999, 18, 3233.
62. Gerloch, M. Inorg. Chem. 1981, 20, 638.
63. Akitsu, T.; Komorita, S.; Urushiyama, A. Bull. Chem. Soc. Jpn. 2001, 74, 851.
64. Dudley, R. J.; Hathaway, B. J.; Hodgson, P. G. J. Chem. Soc., Dalton Trans. 1972, 882.
65. Duggan, M.; Ray, N.; Hathaway, B. J.; Tomlinson, G.; Brint, P.; Pelin, K. J. Chem. Soc., Dalton Trans. 1980, 1342.
66. Addison, A. W.; Hendriks, H. M. J.; Reedijk, J.; Thompson, L. K. Inorg. Chem. 1981, 20, 103.
67. Harrison, W. D.; Kennedy, D. M.; Power, M.; Sheahan, R.; Hathaway, B. J. J. Chem. Soc., Dalton Trans. 1981, 1556.
68. Tyagi, S.; Hathaway, B. J. J. Chem. Soc., Dalton Trans. 1981, 2029.
69. Hathaway, B. J. In Comprehensive Coordination Chemistry; Wilkinson, G., Gillard, R. D., McCleverty, J. A., Eds.; Pergamon Press: Oxford, U.K., 1987; Vol. 5, p 533.
70. Wei, N.; Murthy, N. N.; Karlin, K. D. Inorg. Chem. 1994, 33, 6093.
71. McLachlan, G. A.; Fallon, G. D.; Martin, R. L.; Spiccia, L. Inorg. Chem. 1995, 34, 254.
72. Schatz, M.; Becker, M.; Thaler, F.; Hampel, F.; Schindler, S.; Jacobson, R. R.; Tyeklar, Z.; Murthy, N. N.; Ghosh, P.; Chen, Q.; Zubieta, J.; Karlin, K. D. Inorg. Chem. 2001, 40, 2312.
73. Slade, R. C.; Tomlinson, A. A. G.; Hathaway, B. J.; Billing, D. E. J. Chem. Soc. A 1968, 61.
74. Reinen, D.; Atanasov, M. Chem. Phys. 1989, 136, 27.
75. Procter, I. M.; Hathaway, B. J.; Billing, D. E.; Dudley, R.; Nicholls, P. J. Chem. Soc. A 1969, 1192.
76. Bencini, A.; Gatteschi, D. Inorg. Chem. 1977, 16, 1994.
77. Murakami, T.; Takei, T.; Ishikawa, Y. Polyhedron 1997, 16, 89.
78. Hitchman, M. A. Inorg. Chem. 1974, 13, 2218.
79. Bencini, A.; Bertini, I.; Gatteschi, D.; Scozzafava, A. Inorg. Chem. 1978, 17, 3194.
80. Reinen, D.; Friebel, C. Inorg. Chem. 1984, 23, 791.
81. Kimura, E.; Shionoya, M.; Okamoto, M.; Nada, H. J. Am. Chem. Soc. 1988, 110, 3679.
82. Luo, Q. H.; Zhu, S. R.; Shen, M. C.; Yu, S. Y.; Zhang, Z.; Huang, X. Y.; Wu, Q. J. J. Chem. Soc., Dalton Trans. 1994, 1873.
83. Santos, M. A.; Gaspar, M.; Amorim, M. T. Inorg. Chim. Acta 1999, 284, 20.
84. Barbucci, R.; Bencini, A.; Gatteschi, D. Inorg. Chem. 1977, 16, 2117.
85. Bencini, A.; Gatteschi, D. In Transition Metal Chemistry, A Series Of Advances; Melson, G. A., Figgis, B. N., Eds.; Marcel Dekker: New York, 1965; Vol. 8, p 1.
86. Anda, C.; Bazzicalupi, C.; Bencini, A.; Bianchi, A.; Fornasari, P.; Giorgi, C.; Valtancoli, B.; Lodeiro, C.; Parola, A. J.; Pina, F. Dalton Trans. 2003, 1299.
87. Mendoza, A.; Aguilar, J.; Basallote, M. G.; Gil, L.; Hernandez, J. C.; Manez, M. A.; Garcia-Espana, E.; Ruiz-Ramírez, L.; Soriano, C.; Verdejo, B. Chem. Commun. 2003, 3032.
88. Gans, P.; Sabatini, A.; Vacca, A. Talanta 1996, 43, 1739.
89. Gampp, H.; Maeder, M.; Meyer, C. J.; Zuberbühler, A. D. Talanta 1985, 32, 95.
90. Gampp, H.; Maeder, M.; Meyer, C. J.; Zuberbühler, A. D. Talanta 1985, 32, 251.
91. Gampp, H.; Maeder, M.; Meyer, C. J.; Zuberbühler, A. D. Talanta 1985,32, 1133.
92. Zanello, P.; Cinquantini, A.; Guerriero, P.; Tamburini, S.; Vigato, P. A. Inorg. Chim. Acta 1986, 117, 91.
93. Tana, A. New J. Chem. 2001, 25, 853.
94. Origin 6.0; Microcal Software Inc.: Northampton, MA.
95. COLLECT, Data Collection Software; Nonius, BV: Delft, The Netherlands, 1998.
96. Otwinowski, Z.; Minor, W. Methods Enzymol. 1997, 270, 307.
97. Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A. J. Appl. Crystallogr. 1993, 26, 343.
98. Sheldrick, G. M. SHELXS-97, Program for the Solution of Crystal Structures; University of Göttingen: Göttingen, Germany, 1997.
99. Sheldrick, G. M. SHELXL-97, Program for the Refinement of Crystal Structures; University of Göttingen: Göttingen, Germany, 1997.
100. Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565.
101. Nardelli, M. Comput. Chem. 1983, 7, 95.
102. Nardelli, M. J. Appl. Crystallogr. 1995, 28, 659.
103. Farrugia, L. J. J. Appl. Crystallogr. 1999, 32, 837.
104. Gans, P. Data Fitting in the Chemical Sciences; Wiley: Chichester, U.K., 1992.
105. Lin, X. Q.; Kadish, K. M. Anal. Chem. 1985, 57, 1498.