Unsubstituted cyclidenes - A novel family of lacunar dioxygen carriers with enhanced stability toward autoxidation: Synthesis, characterization, and a representative X-ray structure

Journal of the American Chemical Society

Volumn 119, Issue 18, 1997, Pages 4160-4171

  Kolchinski, A G ^a   Korybut Daszkiewicz, B ^a,c   Rybak Akimova, E V ^a   Busch, D H ^a   Alcock, N W ^b   Clase, H J ^b  

^a UNIVERSITY OF KANSAS   (United States)

^b UNIVERSITY OF WARWICK   (United Kingdom)

^c INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

COBALT DERIVATIVE; OXYGEN;

ARTICLE; AUTOOXIDATION; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CONFORMATION; DISSOCIATION; ELECTROCHEMISTRY; ELECTRON SPIN RESONANCE; OXYGEN AFFINITY; STEREOCHEMISTRY; SYNTHESIS; X RAY ANALYSIS;

EID: 0030902053     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9624477     Document Type: Article

References (51)

1. (a) Haggin, J. Chem. Eng. News 1996, Feb. 5, 35.
2. (b) Busch, D. H.; Alcock, N. W. Chem. Rev. 1994, 94, 585.
3. (c) Li, G. Q.; Govind, R. Ind. Eng. Chem. Res. 1994, 33, 755.
4. (d) Martell, A. E.; Motekaitis, R. J.; Rockcliffe, D.; Menif, R.; Ngwenya, P. M. Pure Appl. Chem. 1994, 66, 859.
5. (e) Traylor, T. G.; Traylor, P. S. Annual Rev. Biophys. Bioeng. 1982, 11, 105.
6. (f) Collman, J. P., Halpert, T. R.; Suslick, K. S. In Metal Ion Activation of Dioxygen; Spiro, T. G., Ed.; Wiley & Sons: New York, 1980.
7. (g) Niederhoffer, E. C.; Timmons, J. H.; Martell, A. E. Chem. Rev. 1984, 84, 137.
8. (h) Smith, T. D.; Pilbrow, J. T. Coord. Chem. Rev. 1981, 39, 295.
9. (i) Jones, R. D.; Summerville, D. A.; Basolo, F. Chem. Rev. 1979, 79, 139.
10. (j) McLendon, G.; Martell, A. E. Coord. Chem. Rev. 1976, 19, 1.
11. (k) Vaska, L. Acc. Chem. Res. 1976, 9, 175.
12. Jaffe, E. R.; Neuman, G. Nature 1964, 202, 607.
13. (a) Hammond, G. S.; Wu, C.-H. Adv. Chem. Series. 1968, 77, 186.
14. (b) Alben, J. O.; Fuchsman, W. H.; Beaudreau, C. A.; Caughey, W. S. Biochemistry 1968, 7, 624.
15. (c) Warburton, P. R.; Busch, D. H. Dynamics of IronII and CobaltII Dioxygen Carriers. In Perspectives on Bioinorganic Chemistry; Hay, R. W., Dilworth, J. R., Nolan, K. B., Eds.; JAI Press Ltd.: London, 1993; Vol. 2, pp 1-79.
16. (a) Collman, J. P.; Gagné, R. R.; Reed, C. A. J. Am. Chem. Soc. 1974, 96, 6522.
17. (b) Collman, J. P.; Elliott, C. M.; Halbert, T. R.; Tovrog, B. S. Proc. Natl. Acad. Sci. U.S.A. 1977, 74, 18.
18. (c) Collman, J. P.; Brauman, J. I.; Collins, T. J.; Iverson, B. L.; Sessler. J. L. J. Am. Chem. Soc. 1981, 103, 2450.
19. (d) Momenteau, M.; Reed, C. A. Chem. Rev. 1994, 94, 659.
20. (a) Wallace, W. J.; Maxwell, J. C.; Caughey, W. S. Biochem. Biophys. Res. Commun. 1974, 57, 4, 1104.
21. (b) Shikama, K. Coord. Chem. Rev. 1988, 83, 73-91.
22. (c) Wallace, W. J.; Houtchens, R. A.; Maxwell, J. C.; Caughey, W. S. J. Biol. Chem. 1982, 257, 4966.
23. Masarwa, M.; Warburton, P. R.; Evans, W. E.; Busch, D. H. Inorg. Chem. 1993, 32, 3826.
24. Goldsby, K. A.; Jircitano, A. J.; Nosco, D. L.; Stevens, J. C.; Busch, D. H. Inorg. Chem. 1990, 29, 2523.
25. Buděšinskỳ, M.; Fiedler, P.; Arnold, Z. Synthesis 1989, 858.
26. Thomas, R.; Fendrick, C. M.; Lin, W.-K.; Glogowski, M. W.; Chavan, M. Y.; Alcock, N. W.; Busch, D. H. Inorg. Chem. 1988, 27, 2534.
27. Korybut-Daszkiewicz, B.; Kojima, M.; Cameron, J. H.; Herron, N.; Chavan, M. Y.; Jircitano, A. J.; Coltrain, B. K.; Neer, G. L.; Alcock, N. W.; Busch, D. H. Inorg. Chem. 1984, 23, 903.
28. Cosier, J.; Glaser, A. M. J. Appl. Cryst. 1986, 19, 105.
29. Alcock, N. W.; Marks, P. J. J. Appl. Cryst. 1994, 27, 200.
30. Sheldrick, G. M. SHELXTL PLUS User's Manual; Nicolet Instr. Co.: Madison, WI, 1986.
31. International Tables for X-ray Crystallography; Kynoch Press: Birmingham, 1974; Vol. IV (Present distributor Kluwer Academic Publishers, Dordrecht).
32. (a) Riley, P. R.; Busch, D. H. Inorg. Synth. 1978, 18, 36.
33. (b) Cairns, C. J.; Busch D. H. Inorg. Synth. 1990, 27, 261.
34. (c) Busch, D. H.; Olszanski, D. J.; Stevens, J. C.; Schammel, W. P.; Kojima, M.; Herron, N.; Zimmer, L. L.; Holter, K. A.; Mocak, J. J. Am. Chem. Soc. 1981, 103, 1472.
35. (d) Busch, D. H.; Christoph, G. G.; Zimmer, L. L.; Jackels, S. C.; Grzybowski, J. J.; Callahan, R. C.; Kojima, M.; Holter, K. A.; Mocak, J.; Herron, N.; Chavan, M.; Schammel, W. P. J. Am. Chem. Soc. 1981, 103, 5107.
36. (e) Busch, D. H.; Jackels, S. C.; Callahan, R. C.; Grzybowski, J. J.; Zimmer, L. L.; Kojima, M.; Olszanski, D. J.; Schammel, W. P.; Stevens, J. C.; Holter, K. A.; Mocak, J. Inorg. Chem. 1981, 20, 2834.
37. Jäger, E. Z. Chem. 1968, 8, 392.
38. Jäger, E. Z. Anorg. Allg. Chem. 1966, 346, 76.
39. (a) Alcock, N. W.; Lin, W.-K.; Jircitano, A.; Mokren, J. D.; Corfield, P. W. R.; Johnson, G.; Novotnak, G.; Cairns, C.; Busch, D. H. Inorg. Chem. 1987, 26, 440.
40. (b) Alcock, N. W.; Lin, W.-K.; Cairns, C.; Pike, G. A.; Busch, D. H. J. Am. Chem. Soc. 1989, 111, 6630.
41. Chavan, M. Y.; Meade, T. J.; Busch, D. H.; Kuwana, T. Inorg. Chem. 1986, 25, 314.
42. Busch, D. H.; Stephenson, N. A. Inclusion Compounds Volume 5: Inorganic and Physical Aspects of Inclusion; Atwood, J., Davies, E., MacNicol, D., Eds.; Oxford University Press: Oxford, 1991; pp 276-310.
43. Drago, R. S.; Corden, B. B. Acc. Chem. Res. 1980, 13, 353.
44. Busch, D. H. In Oxygen Complexes and Oxygen Activation by Transition Metals; Martell, A. E., Sawyer, D. T., Eds.; Plenum Publishing Corporation: 1988.
45. Busch, D. H.; Jackson, P. J.; Kojima, M.; Chmielewski, P.; Matsumoto, N.; Stevens, J. C.; Wu, W.; Nosco, D.; Herron, N.; Ye, N.; Warburton, P. R.; Masarwa, M.; Stephenson, N. A.; Christoph, G.; Alcock, N. W. Inorg. Chem. 1994, 33, 910.
46. Rybak-Akimova, E. V.; Masarwa, M.; Marek, K.; Warburton, P. R.; Busch, D. H. Chem. Commun. 1996, 1451.
47. 2 concentration.
48. 2 concentration.
49. CoC8MeMeMecyclidene (hexafluorophosphate salt) was synthesized according to ref 15b.
50. on (refs 3c and 4d).
51. Chia, P. S. K.; Masarwa, M.; Warburton, P. R.; Wu, W.; Kojima, M.; Nosco, D.; Alcock, N. W.; Busch, D. H. Inorg Chem. 1993, 32, 2736.