Copper(I)/S8 reversible reactions leading to an end-on bound dicopper(II) disulfide complex: Nucleophilic reactivity and analogies to copper-dioxygen chemistry

Journal of the American Chemical Society

Volumn 129, Issue 28, 2007, Pages 8882-8892

  Maiti, Debabrata ^a   Woertink, Julia S ^b   Vance, Michael A ^b   Milligan, Ashley E ^b   Narducci Sarjeant, Amy A ^a   Solomon, Edward I ^b   Karlin, Kenneth D ^a  

^a JOHNS HOPKINS UNIVERSITY   (United States)

^b STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIOXYGEN CHEMISTRY; DISULFUR MOIETY;

CARBONYLATION; COMPLEXATION; SUBSTITUTION REACTIONS; SUBSTRATES;

COPPER;

2,6 DIMETHYLPHENYLISOCYANIDE; COPPER; CYANIDE; DISULFIDE; ISOTHIOCYANIC ACID; LIGAND; METAL COMPLEX; METHYLAMINE; NITROGEN; OXYGEN; SULFUR; TRIS(2 PYRIDYLMETHYL)AMINE; UNCLASSIFIED DRUG; NITROGEN OXIDE;

ARTICLE; CHEMICAL STRUCTURE; COMPLEX FORMATION; QUANTITATIVE ANALYSIS; RAMAN SPECTROMETRY; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS; THERMODYNAMICS; X RAY DIFFRACTION; CHEMISTRY; POLLUTION;

COPPER; DISULFIDES; ENVIRONMENTAL POLLUTION; NITROGEN OXIDES; SULFUR;

EID: 34548391923     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja071968z     Document Type: Article

References (71)

1. Dance, I.; Fisher, K. Prog. Inorg. Chem. 1994, 41, 637-803.
2. Steudel, Y.; Wong, M. W.; Steudel, R. Eur. J. Inorg. Chem. 2005, 2514-2525.
3. Dehnen, S.; Eichhofer, A.; Fenske, D. Eur. J. Inorg. Chem. 2002, 279-317.
4. Donahue, J. P. Chem. Rev. 2006, 106, 4747-4783.
5. Fujisawa, K.; Morooka, Y.; Kitajima, N. J Chem. Soc., Chem. Commun. 1994, 623-624.
6. Helton, M. E.; Chen, P.; Paul, P. P.; Tyeklár, Z.; Sommer, R. D.; Zhakarov, L. N.; Rheingold, A. L.; Solomon, E. I.; Karlin, K. D. J. Am. Chem. Soc. 2003, 125, 1160-1161.
7. Helton, M. E.; Maiti, D.; Zakharov, L. N.; Rheingold, A. L.; Porco, J. A.; Karlin, K. D. Angew. Chem., Int. Ed. 2006, 45, 1138-1141.
8. Lee, Y.; Sarjeant, A. A. N.; Karlin, K. D. Chem. Commun. 2006, 621-623.
9. 2O Binding and Reduction. In Activation of Small Molecules: Organometallic and Bioinorganic Perspectives; Tolman, W. B., Ed.; Wiley-VCH: New York, 2006; pp 43-79.
10. Brown, E. C.; Aboelella, N. W.; Reynolds, A. M.; Aullon, G.; Alvarez, S.; Tolman, W. B. Inorg. Chem. 2004, 43, 3335-3337.
11. Chen, P.; Fujisawa, K.; Helton, M. E.; Karlin, K. D.; Solomon, E. I. J. Am. Chem. Soc. 2003, 125, 6394-6408.
12. Brown, E. C.; York, J. T.; Antholine, W. E.; Ruiz, E.; Alvarez, S.; Tolman, W. B. J. Am. Chem. Soc. 2005, 127, 13752-13753.
13. York, J. T.; Brown, E. C.; Tolman, W. B. Angew. Chem., Int. Ed. 2005, 44, 7745-7748.
14. Tolman, W. B. J. Biol. Inorg. Chem. 2006, 11, 261-271.
15. Brown, E. C.; Bar-Nahum, I.; York, J. T.; Aboelella, N. W.; Tolman, W. B. Inorg. Chem. 2007, 46, 486-496.
16. Gourlay, C.; Nielsen, D. J.; White, J. M.; Knottenbelt, S. Z.; Kirk, M. L.; Young, C. G. J. Am. Chem. Soc. 2006, 128, 2164-2165.
17. Hofmann, M.; Kassube, J.; Graf, T. J. Biol. Inorg. Chem. 2005, 10, 490-495.
18. Resch, M.; Dobbek, H.; Meyer, O. J. Biol. Inorg. Chem. 2005, 10, 518-528.
19. Gorelsky, S. I.; Ghosh, S.; Solomon, E. I. J. Am. Chem. Soc. 2006, 128, 278-290.
20. Chen, P.; Gorelsky, S. I.; Ghosh, S.; Solomon, E. I. Angew. Chem., Int. Ed. 2004, 43, 4132-4140.
21. Paraskevopoulos, K.; Antonyuk, S. V.; Sawers, R. G.; Eady, R. R.; Hasnain, S. S. J. Mol. Biol. 2006, 362, 55-65.
22. Dooley, D. M.; Chan, J. M. Copper Enzymes in Denitrification. In Encyclopedia of Inorganic Chemistry, 2nd ed.; King, R. B., Ed.; Wiley & Sons: Chichester, 2005; Vol. II, pp 1081-1091.
23. Hammerl, A.; Klapötke, T. M. Nitrogen: Inorganic Chemistry. In Encyclopedia of Inorganic Chemistry, 2nd ed.; King, R. B., Ed.; Wiley & Sons: Chichester, 2005; Vol. VI, pp 3531-3599.
24. Leont'ev, A. V.; Fomicheva, O. A.; Proskurnina, M. V.; Zefirov, N. S. Russ. Chem. Rev. 2001, 70, 91-104.
25. Chan, J. M.; Bollinger, J. A.; Grewell, C. L.; Dooley, D. M. J. Am. Chem. Soc. 2004, 126, 3030-3031.
26. Rasmussen, T.; Brittain, T.; Berks, B. C.; Watmough, N. J.; Thomson, A. J. Dalton Trans. 2005, 3501-3506.
27. Lam, W. H.; Cheng, E. C. C.; Yam, V. W. W. Inorg. Chem. 2006, 45, 9434-9441.
28. Yang, R. N.; Sun, Y. A.; Hou, Y. M.; Hu, X. Y.; Jin, D. M. Inorg. Chim. Acta 2000, 304, 1-6.
29. Lucchese, B.; Humphreys, K. J.; Lee, D.-H.; Incarvito, C. D.; Sommer, R. D.; Rheingold, A. L.; Karlin, K. D. Inorg. Chem. 2004, 43, 5987-5998.
30. Liang, H. C.; Kim, E.; Incarvito, C. D.; Rheingold, A. L.; Karlin, K. D. Inorg. Chem. 2002, 41, 2209-2212.
31. Tyeklár, Z.; Jacobson, R. R.; Wei, N.; Murthy, N. N.; Zubieta, J.; Karlin, K. D. J. Am. Chem. Soc. 1993, 115, 2677-2689.
32. Schatz, M.; Becker, M.; Thaler, F.; Hampel, F.; Schindler, S.; Jacobson, R. R.; Tyeklár, Z.; Murthy, N. N.; Ghosh, P.; Chen, Q.; Zubieta, J.; Karlin, K. D. Inorg. Chem. 2001, 40, 2312-2322.
33. Zubieta, J.; Karlin, K. D.; Hayes, J. C. Structural Systematics of Cu(I) and Cu(II) Derivatives of Tripodal Ligands. In Copper Coordination Chemistry: Biochemical and Inorganic Perspectives; Karlin, K. D., Zubieta, J., Eds.; Adenine Press: Albany, NY, 1983; pp 97-108.
34. Karlin, K. D.; Hayes, J. C.; Hutchinson, J. P.; Hyde, J. R.; Zubieta, J. Inorg. Chim. Acta 1982, 64, L219-L220.
35. Jacobson, R. R.; Tyeklár, Z.; Karlin, K. D. Inorg. Chim. Acta 1991, 181, 111-118.
36. Wei, N.; Murthy, N. N.; Chen, Q.; Zubieta, J.; Karlin, K. D. Inorg. Chem. 1994, 33, 1953-1965.
37. Osako, T.; Karlin, K. D.; Itoh, S. Inorg. Chem. 2005, 44, 410-415.
38. Osako, T.; Ueno, Y.; Tachi, Y.; Itoh, S. Inorg. Chem. 2003, 42, 8087-8097.
39. Komiyama, K.; Furutachi, H.; Nagatomo, S.; Hashimoto, A.; Hayashi, H.; Fujinami, S.; Suzuki, M.; Kitagawa, T. Bull. Chem. Soc. Jpn. 2004, 77, 59-72.
40. Jacobson, R. R.; Tyeklár, Z.; Karlin, K. D.; Zubieta, J. Inorg. Chem. 1991, 30, 2035-2040.
41. Lee, D.-H.; Wei, N.; Murthy, N. N.; Tyeklár, Z.; Karlin, K. D.; Kaderli, S.; Jung, B.; Zuberbühler, A. D. J. Am. Chem. Soc. 1995, 117, 12498-12513.
42. Karlin, K. D.; Lee, D.-H.; Kaderli, S.; Zuberbühler, A. D. Chem. Commun. 1997, 475-476.
43. +, indicating loss of sulfur and reduction.
44. -1, very similar to those of complex 2.
45. Skulan, A. J.; Hanson, M. A.; Hsu, H.-f.; Que, L., Jr.; Solomon, E. I. J. Am. Chem. Soc. 2003, 125, 7344-7356.
46. Müller, A.; Jaegermann, W.; Enemark, J. H. Coord. Chem. Rev. 1982, 46, 245-280.
47. Baldwin, M. J.; Ross, P. K.; Pate, J. E.; Tyeklár, Z.; Karlin, K. D.; Solomon, E. I. J. Am. Chem. Soc. 1991, 113, 8671-8679.
48. Quant Hatcher, L.; Karlin, K. D. J. Biol. Inorg. Chem. 2004, 9, 669-683.
49. Lewis, E. A.; Tolman, W. B. Chem. Rev. 2004, 104, 1047-1076.
50. Mirica, L. M.; Ottenwaelder, X.; Stack, T. D. P. Chem. Rev. 2004, 104, 1013-1045.
51. Kurtz, D. M., Jr. Dioxygen-Binding Proteins. In Bio-coordination Chemistry; Que, L., Jr., Tolman, W. B., Eds.; Elsevier: Oxford, 2004; Vol. 8, pp 229-260.
52. Solomon, E. I.; Sundaram, U. M.; Machonkin, T. E. Chem. Rev. 1996, 96, 2563-2605.
53. Paul, P. P.; Tyeklár, Z.; Jacobson, R. R.; Karlin, K. D. J. Am. Chem. Soc 1991, 113, 5322-5332.
54. 2-) complex. With dioxygen and CO, there is a complete lack of reactivity.
55. Zhang, C. X.; Kaderli, S.; Costas, M.; Kim, E.-i.; Neuhold, Y.-M.; Karlin, K. D.; Zuberbühler, A. D. Inorg. Chem. 2003, 42, 1807-1824.
56. Kretzer, R. M.; Ghiladi, R. A.; Lebeau, E. L.; Liang, H.-C.; Karlin, K. D. Inorg. Chem. 2003, 42, 3016-3025.
57. Jardine, F. H. Adv. Inorg. Chem. Radiochem. 1975, 17, 115-163.
58. Floriani, C.; Fiallo, M.; Chiesivilla, A.; Guastini, C. J. Chem. Soc., Dalton Trans. 1987, 1367-1376.
59. Leonard, K.; Plute, K.; Haltiwanger, R. C.; Dubois, M. R. Inorg. Chem. 1979, 18, 3246-3251.
60. Jacob, J.; Espenson, J. H. Chem. Commun. 1999, 1003-1004.
61. Eagle, A. A.; Gable, R. W.; Thomas, S.; Sproules, S. A.; Young, C. G. Polyhedron 2004, 23, 385-394.
62. Matsumoto, K.; Sugiyama, H. J. Organomet. Chem. 2004, 689, 4564-4575.
63. Arisawa, M.; Ashikawa, M.; Suwa, A.; Yamaguchi, M. Tetrahedron Lett. 2005, 46, 1727-1729.
64. Adam, W.; Bargon, R. M. Chem. Rev. 2004, 104, 251-261.
65. Rhames, F. C.; Murthy, N. N.; Karlin, K. D.; Blackburn, N. J. J. Biol. Inorg. Chem. 2001, 6, 567-577.
66. Reedy, B. J.; Murthy, N. N.; Karlin, K. D.; Blackburn, N. J. J. Am. Chem. Soc. 1995, 117, 9826-9831.
67. Toth, A.; Floriani, C.; Chiesivilla, A.; Guastini, C. J. Chem. Soc., Dalton Trans. 1988, 1599-1605.
68. Tatsuno, Y.; Otsuka, S. J. Am. Chem. Soc. 1981, 103, 5832-5839.
69. Otsuka, S.; Nakamura, A.; Tatsuno, Y.; Miki, M. J. Am. Chem. Soc. 1972, 94, 3761-3767.
70. Sheldon, R. A.; Kochi, J. K. Metal-Catalyzed Oxidations of Organic Compounds; Academic Press: New York, 1981.
71. Hatcher, L. Q.; Karlin, K. D. Adv. Inorg. Chem. 2006, 58, 131-184.