First Row Divalent Transition Metal Complexes of Aryl-Appended Tris((pyridyl)methyl)amine Ligands: Syntheses, Structures, Electrochemistry, and Hydroxamate Binding Properties

Inorganic Chemistry

Volumn 42, Issue 23, 2003, Pages 7472-7488

  Makowska Grzyska, Magdalena M ^a   Szajna, Ewa ^a   Shipley, Crystal ^a   Arif, Atta M ^b   Mitchell, Michael H ^c   Halfen, Jason A ^c   Berreau, Lisa M ^a  

^a UTAH STATE UNIVERSITY   (United States)

^b UNIVERSITY OF UTAH   (United States)

^c UNIVERSITY OF WISCONSIN EAU CLAIRE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; AMINE; COBALT COMPLEX; HYDROXAMIC ACID DERIVATIVE; LIGAND; MANGANESE; METAL COMPLEX; METHANOL; N,N BIS[(6 PHENYL 2 PYRIDYL)METHYL] N [(2 PYRIDYL)METHYL]AMINE; NICKEL COMPLEX; TRANSITION ELEMENT; TRIS[(PYRIDYL)METHYL]AMINE; UNCLASSIFIED DRUG; ZINC COMPLEX;

ARTICLE; BINDING AFFINITY; CHELATION; CHEMICAL STRUCTURE; CYCLIC POTENTIOMETRY; ELECTROCHEMISTRY; HYDROGEN BOND; MOLECULAR INTERACTION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0242609386     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic034810y     Document Type: Article

References (88)

1. (a) Woo, E.-J.; Dunwell, J. M.; Goodenough, P. W.; Marvier, A. C.; Pickersgill, R. W. Nat. Struct. Biol. 2000, 11, 1036-1040.
2. (b) Woo, E.-J.; Dunwell, J. M.; Goodenough, P. W.; Pickersgill, R. W. FEBS Lett. 1998, 437, 87-90.
3. Anand, R.; Dorrestein, P. C.; Kinsland, C.; Begley, T. P.; Ealick, S. E. Biochemistry 2002, 41, 7659-7669.
4. (a) Tanner, A.; Bowater, L.; Fairhurst, S. A.; Bornemann, S. J. Biol. Chem. 2001, 47, 43627-43634.
5. (b) Tanner, A.; Bornemann, S. J. Bacteriol. 2000, 182, 5271-5273.
6. (a) Dai, Y.; Pochapsky, T. C.; Abeles, R. H. Biochemistry 2001, 40, 6379-6387.
7. (b) Al-Mjeni, F.; Ju, T.; Pochapsky, T. C.; Maroney, M. J. Biochemistry 2002, 41, 6761-6769.
8. Creighton, D. J.; Hamilton, D. S. Arch. Biochem. Biophys. 2001, 387, 1-10.
9. (a) Chuang, C.-L.; Lim, K. T.; Chen, Q.; Zubieta, J.; Canary, J. W. Inorg. Chem. 1995, 34, 2562-2568.
10. (b) Chuang, C.-L.; Lim, K. T.; Canary, J. W. Supramol. Chem. 1995, 5, 39-43.
11. (a) Mandon, D.; Machkour, A.; Goetz, S.; Welter, R. Inorg. Chem. 2002, 41, 5364-5372.
12. (b) Mandon, D.; Nopper, A.; Litrol, T.; Goetz, S. Inorg. Chem. 2001, 40, 4803-4806.
13. (a) Jensen, M. P.; Lange, S. J.; Mehn, M. P.; Que, E. L.; Que, L., Jr. J. Am. Chem. Soc. 2003, 125, 2113-2128.
14. (b) Lange, S. J.; Miyake, H.; Que, L., Jr. J. Am. Chem. Soc. 1999, 121, 6330-6331.
15. He, Z.; Craig, D. C.; Colbran, S. B. J. Chem. Soc., Dalton Trans. 2002, 4224-4235.
16. Armarego, W. L. F.; Perrin, D. D. Purification of Laboratory Chemicals; 4th Ed.; Butterworth-Heinemann: Boston, MA, 1996.
17. Evans, D. F. J. Chem. Soc. 1959, 2003-2005.
18. Connelly, N. G.; Geiger, W. E. Chem. Rev. 1996, 96, 877-910.
19. Wolsey, W. C. J. Chem. Educ. 1973, 50, A335-A337.
20. Parks, J. E.; Wagner, B. E.; Holm, R. H. Inorg. Chem. 1971, 10, 2472-2478.
21. Otwinowski, Z.; Minor, W. Methods Enzymol. 1997, 276, 307-326.
22. 3TPA. Fe: (a) Jo, D.-H.; Chiou, Y.-M.; Que, L., Jr. Inorg. Chem. 2001, 40, 3181-3190.
23. Cu(II): (b) Nagao, H.; Komeda, N.; Mukaida, M.; Suzuki, M.; Tanaka, K. Inorg. Chem. 1996, 35, 6809-6815.
24. TPA. Cu(I): Tyeklár, Z.; Jacobson, R. R.; Wei, N.; Murthy, N. N.; Zubieta, J.; Karlin, K. D. J. Am. Chem. Soc. 1993, 115, 2677-2689.
25. TPA: (a) Xiang, D. F.; Duan, C. Y.; Tan, X. S.; Liu, Y. J.; Tang, W. X. Polyhedron 1998, 17, 2647-2653.
26. (b) Oshio, H.; Ino, E.; Mogi, I.; Ito, T. Inorg. Chem. 1993, 32, 5697-5703.
27. (c) Towle, D. K.; Botsford, C. A.; Hodgson, D. J. Inorg. Chim. Acta 1988, 141, 167-168.
28. (d) Gultneh, Y.; Farooq, A.; Karlin, K. D.; Liu, S.; Zubieta, J. Inorg. Chim. Acta 1993, 211, 171-175.
29. 2TPA: (e) Goodson, P. A.; Oki, A. R.; Hodgson, D. J. Inorg. Chim. Acta 1990, 177, 59-64.
30. (f) Goodson, P. A.; Oki, A. R.; Glerup, J.; Hodgson, D. J. J. Am. Chem. Soc. 1990, 112, 6248-6254.
31. 3TPA: (g) Reynolds, M. F.; Costas, M.; Ito, M.; Jo, D.-H. ; Tipton, A. A.; Whiting, A. K.; Que, L., Jr. JBIC, J. Biol. Inorg. Chem. 2003, 8, 263-272.
32. (h) Zhang, Z.-H.; Bu, X.-H.; Ma, Z.-H.; Bu, W.-M.; Tang, Y.; Zhao, Q.-H. Polyhedron 2000, 19, 1559-1566.
33. Nishio, M.; Hirota, M.; Umezawa, Y. The CH/π Interaction: Evidence, Nature and Consequences; Wiley-VCH: New York, 1998.
34. (a) Zhang, Z.-H.; Bu, X.-H.; Zhu, Z.-A.; Jiang, Z.-H.; Chen, Y.-T. Transition Met. Chem. 1996, 21, 235-237.
35. (b) Ito, M.; Takita, Y. Chem. Lett. 1996, 929-930.
36. (c) Ito, M.; Sakai, K.; Tsubomura, T.; Takita, Y.-S. Bull. Chem. Soc. Jpn. 1999, 72, 239-247.
37. (d) Tong, B.; Norman, R. E.; Chang, S.-C. Acta Crystallogr. 1999, C55, 1236-1238.
38. (e) Tong, B.; Chang, S.-C.; Carpenter, E. E.; O'Connor, C. J.; Lay, J. O., Jr.; Norman, R. E. Inorg. Chim. Acta 2000, 300, 855-861.
39. (a) Zhang, Z.-H.; Bu, X.-H.; Ma, Z.-H.; Bu, W.-M.; Tang, Y.; Zhao, Q.-H. Polyhedron 2000, 19, 1559-1566.
40. (b) Shiren, K.; Ogo, S.; Fujinami, S.; Hayashi, H.; Suzuki, M.; Uehara, A.; Watanabe, Y.; Moro-oka, Y. J. Am. Chem. Soc. 2000, 122, 254-262.
41. Addison, A. W.; Rao, T. N.; Reedijk, J.; van Rijn, J.; Verschoor, G. C. J. Chem. Soc., Dalton Trans. 1984, 1349-1356.
42. (a) Allen, C. S.; Chuang, C.-L.; Comebise, M.; Canary, J. W. Inorg. Chim. Acta 1995, 239, 29-37.
43. (b) Hilt, G.; Jarbawi, T.; Heineman, W. R.; Steckhan, E. Chem. Eur. J. 1997, 3, 79-88.
44. (c) Nanthakumar, A.; Fox, S.; Murthy, N. N.; Karlin, K. D. J. Am. Chem. Soc. 1997, 119, 3898-3906.
45. (a) Canary, J. W.; Allen, C. S.; Castagnetto, J. M.; Chiu, J. M.; Chiu, Y.-H.; Toscano, P. J.; Wang, Y. Inorg. Chem. 1998, 37, 6255-6262.
46. (b) Adams, H.; Bailey, N. A.; Fenton, D. E.; He, Q.-Y. J. Chem. Soc., Dalton Trans. 1997, 1533-1539.
47. (c) Canary, J. W.; Allen, C. S.; Castagnetto, J. M.; Wang, Y. J. Am. Chem. Soc. 1995, 117, 8484-8485.
48. Jolly, W. L. The Synthesis and Characterization of Inorganic Compounds; Waveland Press: Prospect Heights, IL, 1970.
49. Lever, A. B. P. Inorganic Electronic Spectoscopy, 2nd ed.; Elsevier: Amsterdam, 1984.
50. Murthy, N. N.; Karlin, K. D. J. Chem. Soc., Chem. Commun. 1993, 1236-1238.
51. 1H NMR spectra of bulk samples of 7. Upon heating of the NMR sample at ∼45-50° under vacuum for 12 h, the acetonitrile resonance disappears, but the water resonance remains. This indicates that water coordination is also likely in this complex.
52. Mn(II) complexes of aminohydroxamic acids have been previously reported to form in water solution but were not structurally characterized: Enyedy, E. A.; Csóka, H.; Lazar, I.; Micera, G.; Garribba, E.; Farkas, E. J. Chem. Soc., Dalton Trans. 2002, 2632-2640.
53. Ni(II): (a) Stemmler, A. J.; Kampf, J. W.; Kirk, M. L.; Pecoraro, V. L. J. Am. Chem. Soc. 1995, 117, 6368-6369.
54. (b) Arnold, M.; Brown, D. A.; Deeg, O.; Errington, W.; Haase, W.; Herlihy, K.; Kemp, T. J.; Nimir, H.; Werner, R. Inorg. Chem. 1998, 37, 2920-2925.
55. Zn(lI): Brown, D. A.; Errington, W.; Fitzpatrick, N. J.; Glass, W. K.; Kemp, T. J.; Nimir, H.; Ryan, A. T. Chem. Commun. 2002, 1210-1211.
56. Co(II): Brown, D. A.; Errington, W.; Glass, W. K.; Haase, W.; Kemp, T. J.; Nimir, H.; Ostrovsky, S. M.; Werner, R. Inorg. Chem. 2001, 40, 5962-5971.
57. Santana, M. D.; García, G.; Pérez, J.; Molins, E.; López, G. Inorg. Chem. 2001, 40, 5701-5703.
58. Ruf, M.; Weis, K.; Brasack, I.; Vahrenkamp, H. Inorg. Chim. Acta 1996, 250, 271-281.
59. (a) Puerta, D. T.; Cohen, S. M. Inorg. Chem. 2002, 41, 5075-5082.
60. (b) Puerta, D. T.; Cohen, S. M. Inorg. Chem. 2003, 42, 3423-3430.
61. McMillin, D. R. Electronic Absorption Spectroscopy. In Physical Methods in Bioinorganic Chemistry: Spectroscopy and Magnetism; Que, L., Jr., Ed.; University Science Books: Sausalito, CA, 2000; pp 1-58.
62. Blanchard, S.; Blondin, G.; Rivière, E.; Nierlich, M.; Girerd, J.-J. Inorg. Chem. 2003, 42, 4568-4578.
63. (a) Blanchard, S.; Le Clainche, L.; Rager, M.-N.; Chansou, B.; Tuchagues, J. P.; Duprat, A. F.; Le Mest, Y.; Reinaud, O. Angew. Chem., Int. Ed. 1998, 37, 2732-2735.
64. (b) Rondelez, Y.; Sénèque, O.; Rager, M.-N.; Duprat, A. F. ; Reinaud, O. Chem. Eur. J. 2000, 6, 4218-4226.
65. (c) Sénèque, O.; Rager, M.-N.; Giorgi, M.; Reinaud, O. J. Am. Chem. Soc. 2000,122, 6183-6189.
66. (d) Le Clainche, L.; Giorgo, M.; Reinaud, O. Eur. J. Inorg. Chem. 2000, 1931-1933.
67. (e) Le Clainche, L.; Giorgi, M.; Reinaud, O. Inorg. Chem. 2000, 39, 3436-3437.
68. (f) Sénèque, O.; Giorgi, M.; Reinaud, O. Chem. Commun. 2001, 984-985.
69. (g) Sénèque, O.; Rager, M.-N.; Giorgi, M.; Reinaud, O. J. Am. Chem. Soc. 2001, 123, 8442-8443.
70. (h) Sénèque, O.; Rondelez, Y.; Le Clainche, L.; Inisan, C. ; Rager, M.-N.; Giorgi, M.; Reinaud, O. Eur. J. Inorg. Chem. 2001, 2597-2604.
71. (i) Rondelez, Y.; Bertho, G.; Reinaud, O. Angew. Chem., Int. Ed. 2002. 41, 1044-1046.
72. (j) Sénèque, O.; Campion, M.; Douziech, B.; Giorgi, M.; Rivière, E.; Journaux, Y.; Le Mest, Y.; Reinaud, O. Eur. J. Inorg. Chem. 2002, 2007-2014.
73. (k) Rondelez, Y.; Rager, M.-N.; Duprat, A.; Reinaud, O. J. Am. Chem. Soc. 2002, 124, 1334-1340.
74. Kersting, B. Angew. Chem., Int. Ed. 2001, 40, 3988-3990.
75. Wieser-Jeunesse, C.; Matt, D.; De Cian, A. Angew. Chem., Int. Ed. 1998, 37, 2861-2864.
76. Ooi, T.; Kondo, Y.; Mauroka, K. Angew. Chem., Int. Ed. 1998, 37, 3039-3041.
77. Hecht, S.; Fréchet, J. M. J. Angew. Chem., Int. Ed. 2001, 40, 74-91.
78. (a) Ruf, M.; Vahrenkamp, H. Inorg. Chem. 1996, 35, 6571-6578.
79. (b) Kitajima, N.; Tolman, W. B. Prog. Inorg. Chem. 1995, 43, 419-531.
80. (c) Weis, K.; Vahrenkamp, H. Eur. J. Inorg. Chem. 1998, 271-274.
81. Reinhardt, L. A.; Svedruzic, D.; Chang, C. H.; Cleland, W. W.; Richards, N. G. J. J. Am. Chem. Soc. 2003, 125, 1244-1252.
82. Whittaker, M. M.; Whittaker, J. W. JBIC, J. Biol. Inorg. Chem. 2002, 7, 136-145.
83. The magnetic and EPR properties of dinuclear Mn(II) complexes are of interest toward understanding features of the dinuclear manganese sites found in several enzymes including arginase and catalase: (a) Dubois, L.; Xiang, D.-F.; Tan, X.-S.; Pécaut, J.; Jones, P.; Baudron, S.; Le Pape, L.; Latour, J.-M.; Baffert, C.; Chardon-Noblat, S.; Collomb, M.-N.; Deronzier, A. Inorg. Chem. 2003, 42, 750-760 and references therein.
84. (b) Howard, T.; Telser, J.; DeRose, V. J. Inorg. Chem. 2000, 39, 3379-3385.
85. (c) Hureau, C.; Anxolabehere-Mallart, E.; Nierlich, M.; Gonnet, F.; Riviere, E.; Blondin, G. Eur. J. Inorg. Chem. 2002, 10, 2710-2719.
86. (a) James, B. R.; Williams, R. J. P. J. Chem. Soc. 1961, 2007-2019.
87. (b) Sorrell, T. N.; Jameson, D. L. Inorg. Chem. 1982, 21, 1014-1019.
88. Solvent-coordinated tris((pyridyl)methyl)amine complexes of Ni(II) and Co(II) akin to 2, 3, and 5 have been structurally characterized; however, the electrochemical properties of these complexes were not reported.