Models for Arginine-Metal Binding. Synthesis of Guanidine and Urea Ligands through Amination and Hydration of a Cyanamide Ligand Bound to Platinum(II), Osmium(III), and Cobalt(III)

Inorganic Chemistry

Volumn 36, Issue 6, 1997, Pages 1020-1028

  Fairlie, David P ^a,b   Jackson, W Gregory ^c   Skelton, Brian W ^d   Wen, Huo ^d   White, Allan H ^d   Wickramasinghe, Wasantha A ^a   Woon, Tai Chin ^a   Taube, Henry ^b  

^a UNIVERSITY OF QUEENSLAND   (Australia)

^b STANFORD UNIVERSITY   (United States)

^c UNIVERSITY OF NEW SOUTH WALES   (Australia)

^d UNIVERSITY OF WESTERN AUSTRALIA   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001551587     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic961138e     Document Type: Article

References (60)

1. Przybyla, A. E.; Robbins, J.; Menon, N.; Peck, H, D., Jr. FEMS Microbiol. Rev. 1992, 88, 109.
2. (a) Ratilla, E. M. A.; Scott, B. K.: Moxness, M. S.; Kostic, N. M. Inorg. Chem. 1990, 29, 918.
3. (b) Ratilla, E. M, A.; Kostic, N. M. J. Am. Chem. Soc. 1988, 110, 4427.
4. (a) Canty, A. J.; Chaichit, N.; Gatehouse, B. M, Acta Crystallogr. 1979. B35, 592.
5. (b) Canty, A. J.; Fyfe, M.; Gatehouse, B. M. Inorg. Chem. 1978, 17, 1467.
6. Vries, N.; Costello, C. E.; Jones, A. G.; Davison, A. Inorg. Chem. 1990, 29, 1348.
7. (a) Sulfaguanidine : Alleaume, M.; Gulko, A.; Herbstein, F. H.; Kapon, M.; Marsh, R. E. Acta Crystallogr. 1976, B32, 669. (b) Cimetidine: Soto, L.; Legros, J. P.; Sancho, A. Polyhedron 1988, 7, 307. Cyanoguanidine: Begley, M. J.; Hubberstey, P.; Wallon, P. H. J. Chem. Soc., Chem. Commun. 1989, 502.
8. (a) Sulfaguanidine : Alleaume, M.; Gulko, A.; Herbstein, F. H.; Kapon, M.; Marsh, R. E. Acta Crystallogr. 1976, B32, 669. (b) Cimetidine: Soto, L.; Legros, J. P.; Sancho, A. Polyhedron 1988, 7, 307. Cyanoguanidine: Begley, M. J.; Hubberstey, P.; Wallon, P. H. J. Chem. Soc., Chem. Commun. 1989, 502.
9. (a) Sulfaguanidine : Alleaume, M.; Gulko, A.; Herbstein, F. H.; Kapon, M.; Marsh, R. E. Acta Crystallogr. 1976, B32, 669. (b) Cimetidine: Soto, L.; Legros, J. P.; Sancho, A. Polyhedron 1988, 7, 307. Cyanoguanidine: Begley, M. J.; Hubberstey, P.; Wallon, P. H. J. Chem. Soc., Chem. Commun. 1989, 502.
10. (a) Taube, H. Pure Appl. Chem. 1979, 57, 901,
11. (b) Taube, H. Coord. Chem. Rev. 1978, 26, 33.
12. (c) Taube, H. Comments Inorg. Chem. 1981, 1, 17.
13. (a) Nagasawa, T.; Yamada, H. Biochem. Biophys. Res. Commun. 1987, 147, 701.
14. (b) Thompson, L. A.; Knowles, C. J.; Linton, E. A.; Wyatt, J. M. Chem. Br. 1988, 900.
15. (c) Hönicke-Schmidt, P.; Schneider, M. P. J. Chem. Soc., Chem. Commun. 1990, 648.
16. (d) Jin, H.; Turner, I. M.; Nelson, M. J.; Gubriel, R. J.; Doan, P. E.; Huffman, B. M. J. Am. Chem. Soc. 1993, 115, 5290.
17. N-bonded ureas on Co(III): (a) Fairlie, D. P.; Jackson, W. G. Inorg. Chim. Acta 1988. 150, 81. (b) Dixon, A. M.; Fairlie, D. P.; Jackson, W. G.; Sargeson, A. M, Inorg. Chem. 1983, 22, 4038. On Rh(III): (c) Curtis, N. J.; Dixon, N. E.; Sargeson, A. M. J. Am. Chem. Soc. 1983, 105, 5347. On Ru(HI): (d) Fairlie, D. P.; Taube, H. Inorg. Chem. 1985, 24, 3199. On Pt(II): (e) Woon, T. C.; Wickramasinghe, W. A.; Fairlie, D. P. Inorg. Chem. 1993, 32, 2190. On Os(III) and Ru(III); (f) Fairlie, D. P.; Taube, H. To be submitted for publication. On Cu(II) and Ni(II): (g) Maslak, P.; Sczepanski, J. L.; Parvez, M. J. Am. Chem. Soc. 1991, 113, 1062.
18. N-bonded ureas on Co(III): (a) Fairlie, D. P.; Jackson, W. G. Inorg. Chim. Acta 1988. 150, 81. (b) Dixon, A. M.; Fairlie, D. P.; Jackson, W. G.; Sargeson, A. M, Inorg. Chem. 1983, 22, 4038. On Rh(III): (c) Curtis, N. J.; Dixon, N. E.; Sargeson, A. M. J. Am. Chem. Soc. 1983, 105, 5347. On Ru(HI): (d) Fairlie, D. P.; Taube, H. Inorg. Chem. 1985, 24, 3199. On Pt(II): (e) Woon, T. C.; Wickramasinghe, W. A.; Fairlie, D. P. Inorg. Chem. 1993, 32, 2190. On Os(III) and Ru(III); (f) Fairlie, D. P.; Taube, H. To be submitted for publication. On Cu(II) and Ni(II): (g) Maslak, P.; Sczepanski, J. L.; Parvez, M. J. Am. Chem. Soc. 1991, 113, 1062.
19. N-bonded ureas on Co(III): (a) Fairlie, D. P.; Jackson, W. G. Inorg. Chim. Acta 1988. 150, 81. (b) Dixon, A. M.; Fairlie, D. P.; Jackson, W. G.; Sargeson, A. M, Inorg. Chem. 1983, 22, 4038. On Rh(III): (c) Curtis, N. J.; Dixon, N. E.; Sargeson, A. M. J. Am. Chem. Soc. 1983, 105, 5347. On Ru(HI): (d) Fairlie, D. P.; Taube, H. Inorg. Chem. 1985, 24, 3199. On Pt(II): (e) Woon, T. C.; Wickramasinghe, W. A.; Fairlie, D. P. Inorg. Chem. 1993, 32, 2190. On Os(III) and Ru(III); (f) Fairlie, D. P.; Taube, H. To be submitted for publication. On Cu(II) and Ni(II): (g) Maslak, P.; Sczepanski, J. L.; Parvez, M. J. Am. Chem. Soc. 1991, 113, 1062.
20. N-bonded ureas on Co(III): (a) Fairlie, D. P.; Jackson, W. G. Inorg. Chim. Acta 1988. 150, 81. (b) Dixon, A. M.; Fairlie, D. P.; Jackson, W. G.; Sargeson, A. M, Inorg. Chem. 1983, 22, 4038. On Rh(III): (c) Curtis, N. J.; Dixon, N. E.; Sargeson, A. M. J. Am. Chem. Soc. 1983, 105, 5347. On Ru(HI): (d) Fairlie, D. P.; Taube, H. Inorg. Chem. 1985, 24, 3199. On Pt(II): (e) Woon, T. C.; Wickramasinghe, W. A.; Fairlie, D. P. Inorg. Chem. 1993, 32, 2190. On Os(III) and Ru(III); (f) Fairlie, D. P.; Taube, H. To be submitted for publication. On Cu(II) and Ni(II): (g) Maslak, P.; Sczepanski, J. L.; Parvez, M. J. Am. Chem. Soc. 1991, 113, 1062.
21. N-bonded ureas on Co(III): (a) Fairlie, D. P.; Jackson, W. G. Inorg. Chim. Acta 1988. 150, 81. (b) Dixon, A. M.; Fairlie, D. P.; Jackson, W. G.; Sargeson, A. M, Inorg. Chem. 1983, 22, 4038. On Rh(III): (c) Curtis, N. J.; Dixon, N. E.; Sargeson, A. M. J. Am. Chem. Soc. 1983, 105, 5347. On Ru(HI): (d) Fairlie, D. P.; Taube, H. Inorg. Chem. 1985, 24, 3199. On Pt(II): (e) Woon, T. C.; Wickramasinghe, W. A.; Fairlie, D. P. Inorg. Chem. 1993, 32, 2190. On Os(III) and Ru(III); (f) Fairlie, D. P.; Taube, H. To be submitted for publication. On Cu(II) and Ni(II): (g) Maslak, P.; Sczepanski, J. L.; Parvez, M. J. Am. Chem. Soc. 1991, 113, 1062.
22. N-bonded ureas on Co(III): (a) Fairlie, D. P.; Jackson, W. G. Inorg. Chim. Acta 1988. 150, 81. (b) Dixon, A. M.; Fairlie, D. P.; Jackson, W. G.; Sargeson, A. M, Inorg. Chem. 1983, 22, 4038. On Rh(III): (c) Curtis, N. J.; Dixon, N. E.; Sargeson, A. M. J. Am. Chem. Soc. 1983, 105, 5347. On Ru(HI): (d) Fairlie, D. P.; Taube, H. Inorg. Chem. 1985, 24, 3199. On Pt(II): (e) Woon, T. C.; Wickramasinghe, W. A.; Fairlie, D. P. Inorg. Chem. 1993, 32, 2190. On Os(III) and Ru(III); (f) Fairlie, D. P.; Taube, H. To be submitted for publication. On Cu(II) and Ni(II): (g) Maslak, P.; Sczepanski, J. L.; Parvez, M. J. Am. Chem. Soc. 1991, 113, 1062.
23. N-bonded ureas on Co(III): (a) Fairlie, D. P.; Jackson, W. G. Inorg. Chim. Acta 1988. 150, 81. (b) Dixon, A. M.; Fairlie, D. P.; Jackson, W. G.; Sargeson, A. M, Inorg. Chem. 1983, 22, 4038. On Rh(III): (c) Curtis, N. J.; Dixon, N. E.; Sargeson, A. M. J. Am. Chem. Soc. 1983, 105, 5347. On Ru(HI): (d) Fairlie, D. P.; Taube, H. Inorg. Chem. 1985, 24, 3199. On Pt(II): (e) Woon, T. C.; Wickramasinghe, W. A.; Fairlie, D. P. Inorg. Chem. 1993, 32, 2190. On Os(III) and Ru(III); (f) Fairlie, D. P.; Taube, H. To be submitted for publication. On Cu(II) and Ni(II): (g) Maslak, P.; Sczepanski, J. L.; Parvez, M. J. Am. Chem. Soc. 1991, 113, 1062.
24. (a) Andrews, R. K.; Blakeley, R. L.; Zerner, B. In The Bioinorganic Chemistry of Nickel; Lancaster, J. R., Jr., Ed.; VCH Publishers: New York, 1988; p 141.
25. (b) Hausinger, R. P. Biochemistry of Nickel. In Biochemistry of the Elements, Plenum Press: New York, 1993; Vol. 12, Chapter 3, p 23.
26. Curtis, N. J.; Sargeson, A. M. J. Am. Chem. Soc. 1984, 106, 625.
27. Dixon, N. E.; Jackson, W. G.; Lancaster, M. J.: Lawrance, G. A.; Sargeson, A. M. Inorg. Chem. 1981, 20, 470.
28. Lay, P. A.; Magnuson, R. H.; Taube, H. J. Am. Chem. Soc. 1982, 104, 7685.
29. Woon, T. C; Fairlie, D. P. Inorg. Chem. 1992, 31, 4069.
30. Johnson, A.; Taube, H. Indian J. Chem. 1989, 66, 503.
31. (a) Zanella, A. W.; Ford, P. C. Inorg. Chem. 1975, 14, 42.
32. (b) Zanella. A. W.; Ford, P. C. Inorg. Chem. 1975, 14, 700.
33. (c) Zanella, A. W.; Ford, P. C. J. Chem. Soc., Chem, Commun. 1975, 795.
34. (d) Clarke, R. E.; Ford, P. C. Inorg. Chem. 1970, 9, 227.
35. (e) Foust, R. D.; Ford, P. C. Inorg. Chem. 1972, 11, 899.
36. (a) Buckingham, D. A.; Keene, F. R.; Sargeson, A. M. J. Am. Chem. Soc. 1973, 95, 5649.
37. (b) Butler, D. G.; Greaser, I. I.; Dyke, S. F.; Sargeson, A. M. Acta Chem. Scand., A 1978, 32, 789.
38. (c) Creaser, I. L; Harrowfield, J. MacB.; Keene, F. R.; Sargeson, A, M. J. Am. Chem. Soc. 1981, 103, 3559.
39. (d) Pinnell, D.; Wright, G. B.; Jordan, R. B. J. Am. Chem. Soc. 1972, 94, 6104.
40. (e) Balahura, R. J.: Cock, P.; Purcell, W. L. J. Am. Chem. Soc. 1974, 96, 2739.
41. (f) Balahura, R. J.; Purcell, W. L. Inorg. Chem. 1981, 20, 4159.
42. (g) Jordan, R. B.; Sargeson, A. M.; Taube, H. Inorg. Chem. 1966, 5, 1091.
43. (a) Angel, R.; Fairlie. D. P.; Jackson, W. G. Inorg. Chem. 1990, 29, 20.
44. (b) Fairlie, D. P.; Angus, P. M.; Fenn, M. D.; Jackson, W. G. Inorg. Chem. 1991, 30, 1564.
45. Fairlie, D. P.; Woon, T. C; Wickramasinghe, W. A.; Willis, A. C. Inorg. Chem. 1994, 33, 6425.
46. Metal activation of other nitriles (a) Breslow, R.; Fatrweather, R.; Keana, J. J. Am. Chem. Soc: 1967, 59, 2135. (b) Bennett, M. A.; Yoshida, T. J. Am. Chem. Soc. 1973, 95, 3030. Diamond, S. E.; Grant, B.; Tom, G. M.; Taube, H. Tetrahedron Lett. 1974, 46, 4025. Jensen, C. M.; Trogler, W. C J. Am. Chem. Soc. 1986, 108, 723. (e) Ellis, W. R., Jr.; Purcell, W. L. Inorg. Chem. 1990, 29, 140. (f) Kim, J. H.; Britten, J.; Chin, J. J. Am. Chem. Soc. 1993, 115, 3618.
47. Metal activation of other nitriles (a) Breslow, R.; Fatrweather, R.; Keana, J. J. Am. Chem. Soc: 1967, 59, 2135. (b) Bennett, M. A.; Yoshida, T. J. Am. Chem. Soc. 1973, 95, 3030. Diamond, S. E.; Grant, B.; Tom, G. M.; Taube, H. Tetrahedron Lett. 1974, 46, 4025. Jensen, C. M.; Trogler, W. C J. Am. Chem. Soc. 1986, 108, 723. (e) Ellis, W. R., Jr.; Purcell, W. L. Inorg. Chem. 1990, 29, 140. (f) Kim, J. H.; Britten, J.; Chin, J. J. Am. Chem. Soc. 1993, 115, 3618.
48. Metal activation of other nitriles (a) Breslow, R.; Fatrweather, R.; Keana, J. J. Am. Chem. Soc: 1967, 59, 2135. (b) Bennett, M. A.; Yoshida, T. J. Am. Chem. Soc. 1973, 95, 3030. Diamond, S. E.; Grant, B.; Tom, G. M.; Taube, H. Tetrahedron Lett. 1974, 46, 4025. Jensen, C. M.; Trogler, W. C J. Am. Chem. Soc. 1986, 108, 723. (e) Ellis, W. R., Jr.; Purcell, W. L. Inorg. Chem. 1990, 29, 140. (f) Kim, J. H.; Britten, J.; Chin, J. J. Am. Chem. Soc. 1993, 115, 3618.
49. Metal activation of other nitriles (a) Breslow, R.; Fatrweather, R.; Keana, J. J. Am. Chem. Soc: 1967, 59, 2135. (b) Bennett, M. A.; Yoshida, T. J. Am. Chem. Soc. 1973, 95, 3030. Diamond, S. E.; Grant, B.; Tom, G. M.; Taube, H. Tetrahedron Lett. 1974, 46, 4025. Jensen, C. M.; Trogler, W. C J. Am. Chem. Soc. 1986, 108, 723. (e) Ellis, W. R., Jr.; Purcell, W. L. Inorg. Chem. 1990, 29, 140. (f) Kim, J. H.; Britten, J.; Chin, J. J. Am. Chem. Soc. 1993, 115, 3618.
50. Metal activation of other nitriles (a) Breslow, R.; Fatrweather, R.; Keana, J. J. Am. Chem. Soc: 1967, 59, 2135. (b) Bennett, M. A.; Yoshida, T. J. Am. Chem. Soc. 1973, 95, 3030. Diamond, S. E.; Grant, B.; Tom, G. M.; Taube, H. Tetrahedron Lett. 1974, 46, 4025. Jensen, C. M.; Trogler, W. C J. Am. Chem. Soc. 1986, 108, 723. (e) Ellis, W. R., Jr.; Purcell, W. L. Inorg. Chem. 1990, 29, 140. (f) Kim, J. H.; Britten, J.; Chin, J. J. Am. Chem. Soc. 1993, 115, 3618.
51. Metal activation of other nitriles (a) Breslow, R.; Fatrweather, R.; Keana, J. J. Am. Chem. Soc: 1967, 59, 2135. (b) Bennett, M. A.; Yoshida, T. J. Am. Chem. Soc. 1973, 95, 3030. Diamond, S. E.; Grant, B.; Tom, G. M.; Taube, H. Tetrahedron Lett. 1974, 46, 4025. Jensen, C. M.; Trogler, W. C J. Am. Chem. Soc. 1986, 108, 723. (e) Ellis, W. R., Jr.; Purcell, W. L. Inorg. Chem. 1990, 29, 140. (f) Kim, J. H.; Britten, J.; Chin, J. J. Am. Chem. Soc. 1993, 115, 3618.
52. (a) Stephenson, N. C. J. Inorg. Nucl. Chem. 1962, 24, 801.
53. (b) Fairlie, D. P.; Jackson, W. G. Inorg. Chem. 1990, 29, 140.
54. Balahura, R. J.; Jordan, R. B, J. Am. Chem. Soc. 1971, 93, 625.
55. -, see ref 16b.
56. -, see ref 16c.
57. -, see ref 16c.
58. Brown, G. M.; Simon, J. E.; Taube, H. J. Am, Chem. Soc. 1978, 100, 2767.
59. See ref 13, footnote 21.
60. Hall, S. R.; Stewart, J. M., Eds. The XTAL 3.0 Reference Manual; Universities of Western Australia and Maryland: Nedlands, Australia, and College Park, MD. 1990.