Sulfur donor atom effects on copper(I)/O2 chemistry with thioanisole containing tetradentate N3S ligand leading to μ-1,2-peroxo-dicopper(II) species

Inorganic Chemistry

Volumn 49, Issue 19, 2010, Pages 8873-8885

  Lee, Yunho ^a   Lee, Dong Heon ^b   Park, Ga Young ^a   Lucas, Heather R ^a   Narducci Sarjeant, Amy A ^a   Kieber Emmons, Matthew T ^c   Vance, Michael A ^c   Milligan, Ashley E ^c   Solomon, Edward I ^c   Karlin, Kenneth D ^a  

^a JOHNS HOPKINS UNIVERSITY   (United States)

^b Chonbuk National University   (South Korea)

^c STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER; LIGAND; ORGANOMETALLIC COMPOUND; OXYGEN; PEROXIDE; PYRIDINE DERIVATIVE; SULFIDE; SULFUR; THIOANISOLE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

COPPER; LIGANDS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; OXYGEN; PEROXIDES; PYRIDINES; STEREOISOMERISM; SULFIDES; SULFUR;

EID: 77957275345     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic101041m     Document Type: Article

References (83)

1. Hatcher, L. Q. and Karlin, K. D. J. Biol. Inorg. Chem. 2004, 9, 669-683
2. Mirica, L. M., Ottenwaelder, X., and Stack, T. D. P. Chem. Rev. 2004, 104, 1013-1045
3. Lewis, E. A. and Tolman, W. B. Chem. Rev. 2004, 104, 1047-1076
4. Jacobson, R. R., Tyeklár, Z., Karlin, K. D., Liu, S., and Zubieta, J. J. Am. Chem. Soc. 1988, 110, 3690-3692
5. Tyeklár, Z., Jacobson, R. R., Wei, N., Murthy, N. N., Zubieta, J., and Karlin, K. D. J. Am. Chem. Soc. 1993, 115, 2677-2689
6. Karlin, K. D., Kaderli, S., and Zuberbühler, A. D. Acc. Chem. Res. 1997, 30, 139-147
7. Zhang, C. X., Kaderli, S., Costas, M., Kim, E.-i., Neuhold, Y.-M., Karlin, K. D., and Zuberbühler, A. D. Inorg. Chem. 2003, 42, 1807-1824
8. Fry, H. C., Scaltrito, D. V., Karlin, K. D., and Meyer, G. J. J. Am. Chem. Soc. 2003, 125, 11866-11871
9. Lee, Y., Park, G. Y., Lucas, H. R., Vajda, P. L., Kamaraj, K., Vance, M. A., Milligan, A. E., Woertink, J. S., Siegler, M. A., Narducci Sarjeant, A. A., Zakharov, L. N., Rheingold, A. L., Solomon, E. I., and Karlin, K. D. Inorg. Chem. 2009, 48, 11297-11309
10. Himes, R. A. and Karlin, K. D. Curr. Opin. Chem. Biol. 2009, 13, 119-131
11. Lucas, H. R. and Karlin, K. D. Met. Ions Life Sci. 2009, 6, 295-361
12. Sarangi, R., York, J. T., Helton, M. E., Fujisawa, K., Karlin, K. D., Tolman, W. B., Hodgson, K. O., Hedman, B., and Solomon, E. I. J. Am. Chem. Soc. 2008, 130, 676-686
13. Itoh, S. and Fukuzumi, S. Acc. Chem. Res. 2007, 40, 592-600
14. Cramer, C. and Tolman, W. Acc. Chem. Res. 2007, 40, 601-608
15. Klinman, J. P. J. Biol. Chem. 2006, 281, 3013-3016
16. Prigge, S. T., Eipper, B., Mains, R., and Amzel, L. M. Science 2004, 304, 864-867
17. Prigge, S. T., Mains, R. E., Eipper, B. A., and Amzel, L. M. Cell. Mol. Life Sci. 2000, 57, 1236-1259
18. Prigge, S. T., Kolhekar, A., Eipper, B. A., Mains, R. E., and Amzel, M. Science 1997, 278, 1300-1305
19. Evans, J. P., Ahn, K., and Klinman, J. P. J. Biol. Chem. 2003, 278, 49691-49698
20. Chen, P. and Solomon, E. I. J. Am. Chem. Soc. 2004, 126, 4991-5000
21. Chen, P., Bell, J., Eipper, B. A., and Solomon, E. I. Biochemistry 2004, 43, 5735-5747
22. Chen, P. and Solomon, E. I. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 13105-13110
23. Decker, A. and Solomon, E. I. Curr. Opin. Chem. Biol. 2005, 9, 152-163
24. Hatcher, L. Q., Lee, D.-H., Vance, M. A., Milligan, A. E., Sarangi, R., Hodgson, K. O., Hedman, B., Solomon, E. I., and Karlin, K. D. Inorg. Chem. 2006, 45, 10055-10057
25. Lee, D. H., Hatcher, L. Q., Vance, M. A., Sarangi, R., Milligan, A. E., Narducci Sarjeant, A. A., Incarvito, C. D., Rheingold, A. L., Hodgson, K. O., Hedman, B., Solomon, E. I., and Karlin, K. D. Inorg. Chem. 2007, 46, 6056-6068
26. Liang, H.-C., Kim, E., Incarvito, C. D., Rheingold, A. L., and Karlin, K. D. Inorg, Chem. 2002, 41, 2209-2212
27. Liang, H.-C., Karlin, K. D., Dyson, R., Kaderli, S., Jung, B., and Zuberbühler, A. D. Inorg. Chem. 2000, 39, 5884-5894
28. Geary, W. J. Coord. Chem. Rev. 1971, 7, 81-122
29. Sorrell, T. N. and Borovik, A. S. J. Am. Chem. Soc. 1987, 109, 4255-4260
30. Connelly, N. G. and Geiger, W. E. Chem. Rev. 1996, 96, 877-910
31. Karlin, K. D., Nasir, M. S., Cohen, B. I., Cruse, R. W., Kaderli, S., and Zuberbühler, A. D. J. Am. Chem. Soc. 1994, 116, 1324-1336
32. Sanyal, I., Mahroof-Tahir, M., Nasir, S., Ghosh, P., Cohen, B. I., Gultneh, Y., Cruse, R., Farooq, A., Karlin, K. D., Liu, S., and Zubieta, J. Inorg. Chem. 1992, 31, 4322-4332
33. Rorabacher, D. B. Chem. Rev. 2004, 104, 651-697
34. Ambundo, E. a., Yu, Q. Y., Ochrymowycz, L. A., and Rorabacher, D. B. Inorg. Chem. 2003, 42, 5267-5273
35. Karlin, K. D. and Yandell, J. K. Inorg. Chem. 1984, 23, 1184-1188
36. Alzuet, G., Casella, L., Villa, M. L., Carugo, O., and Gullotti, M. J. Chem. Soc., Dalton Trans. 1997, 4789-4794
37. Nasir, M. S., Cohen, B. I., and Karlin, K. D. J. Am. Chem. Soc. 1992, 114, 2482-2494
38. Pidcock, E., Obias, H. V., Zhang, C. X., Karlin, K. D., and Solomon, E. I. J. Am. Chem. Soc. 1998, 120, 7841-7847
39. Champloy, F., Benali-Cherif, N., Bruno, P., Blain, I., Pierrot, M., Reglier, M., and Michalowicz, A. Inorg. Chem. 1998, 37, 3910-3918
40. Ohta, T., Tachiyama, T., Yoshizawa, K., Yamabe, T., Uchida, T., and Kitagawa, T. Inorg. Chem. 2000, 39, 4358-4369
41. Kodera, M., Kita, T., Miura, I., Nakayama, N., Kawata, T., Kano, K., and Hirota, S. J. Am. Chem. Soc. 2001, 123, 7715-7716
42. Santra, B. K., Reddy, P. A. N., Nethaji, M., and Chakravarty, A. R. Inorg. Chem. 2002, 41, 1328-1332
43. Aboelella, N. W., Gherman, B. F., Hill, L. M. R., York, J. T., Holm, N., Young, V. G., Cramer, C. J., and Tolman, W. B. J. Am. Chem. Soc. 2006, 128, 3445-3458
44. Zhou, L., Powell, D., and Nicholas, K. M. Inorg. Chem. 2006, 45, 3840-3842
45. Zhou, L., Powell, D., and Nicholas, K. M. Inorg. Chem. 2007, 46, 7789-7799
46. Park, G. Y., Lee, Y., Lee, D.-H., Woertink, J. S., Sarjeant, A. A. N., Solomon, E. I., and Karlin, K. D. Chem. Commun. 2010, 46, 91-93
47. Osako, T., Terada, S., Tosha, T., Nagatomo, S., Furutachi, H., Fujinami, S., Kitagawa, T., Suzuki, M., and Itoh, S. Dalton Trans. 2005, 3514-3521
48. Pasquali, M., Marini, G., Floriani, C., Gaetanimanfredotti, A., and Guastini, C. Inorg. Chem. 1980, 19, 2525-2531
49. Jonas, R. T. and Stack, T. D. P. Inorg. Chem. 1998, 37, 6615-6629
50. Kitajima, N., Fujisawa, K., Fujimoto, C., Moro-oka, Y., Hashimoto, S., Kitagawa, T., Toriumi, K., Tatsumi, K., and Nakamura, A. J. Am. Chem. Soc. 1992, 114, 1277-1291
51. Dias, H. V. R. and Lovely, C. J. Chem. Rev. 2008, 108, 3223-3238
52. Kealey, S., Miller, P. W., Long, N. J., Plisson, C., Martarello, L., and Gee, A. D. Chem. Commun. 2009, 3696-3698
53. Fujisawa, K., Ono, T., Ishikawa, Y., Amir, N., Miyashita, Y., Okamoto, K., and Lehnert, N. Inorg. Chem. 2006, 45, 1698-1713
54. Rondelez, Y., Séneque, O., Rager, M.-N., Duprat, A. F., and Reinaud, O. Chem. - Eur. J. 2000, 6, 4218-4226
55. Kretzer, R. M., Ghiladi, R. A., Lebeau, E. L., Liang, H.-C., and Karlin, K. D. Inorg. Chem. 2003, 42, 3016-3025
56. Fry, H. C., Lucas, H. R., Narducci Sarjeant, A. A., Karlin, K. D., and Meyer, G. J. Inorg. Chem. 2008, 47, 241-256
57. Ambundo, E. A., Deydier, M.-V., Grall, A. J., Aguera-Vega, N., Dressel, L. T., Cooper, T. H., Heeg, M. J., Ochrymowycz, L. A., and Rorabacher, D. B. Inorg. Chem. 1999, 38, 4233-4242
58. Fry, H. C. Ph.D. Dissertation, Johns Hopkins University, Baltimore, MD, 2004.
59. Gilbert, J. G., Addison, A. W., Nazarenko, A. Y., and Butcher, R. J. Inorg. Chim. Acta 2001, 324, 123-130
60. Description of the coordination geometry around Cu(II) in each complex, 1c and 2c, as if they were pentacoordinate and without the axially weakly bound perchlorate O-donor, indicates that both are distorted from square-based pyramidal, τ = 0.24 and 0.25, respectively; τ = 0.0 for a perfect square pyramid (SP); τ = 1 for a perfect trigonal bipyramidal (TBP) geometry; see: Addison, A. W., Rao, T. N., Reedijk, J., van Rijn, J., and Verschoor, G. C. J. Chem. Soc., Dalton Trans. 1984, 1349-1356
61. Karlin, K. D., Hayes, J. C., Shi, J., Hutchinson, J. P., and Zubieta, J. Inorg. Chem. 1982, 21, 4106-4108
62. Zubieta, J., Karlin, K. D., and 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. and Zubieta, J., Eds.; Adenine Press: Albany, NY, 1983; pp 97 - 108.
63. Fox, S., Nanthakumar, A., Wikström, M., Karlin, K. D., and Blackburn, N. J. J. Am. Chem. Soc. 1996, 118, 24-34
64. Lee, Y., Lee, D. H., Narducci Sarjeant, A. A., Zakharov, L. N., Rheingold, A. L., and Karlin, K. D. Inorg. Chem. 2006, 45, 10098-10107
65. Aronne, L., Dunn, B. C., Vyvyan, J. R., Souvignier, C. W., Mayer, M. J., Howard, T. A., Salhi, C. A., Goldie, S. N., Ochrymowycz, L. A., and Rorabacher, D. B. Inorg. Chem. 1995, 34, 357-369
66. Mandal, S. and Bharadwaj, P. K. Indian J. Chem. 1991, 30A, 948-951
67. Bouwman, E., Driessen, W. L., and Reedijk, J. Coord. Chem. Rev. 1990, 104, 143-172
68. Solomon, E. I., Penfield, K. W., and Wilcox, D. E. Struct. Bonding (Berlin) 1983, 53, 1-57
69. Nikles, D. E., Powers, M. J., and Urbach, F. L. Inorg. Chem. 1983, 22, 3210-3217
70. Ferris, N. S., Woodruff, W. H., Rorabacher, D. B., Jones, T. E., and Ochrymowycz, L. A. J. Am. Chem. Soc. 1978, 100, 5939-5942
71. Amundsen, A. R., Whelan, J., and Bosnich, B. J. Am. Chem. Soc. 1977, 99, 6730-6739
72. Miskowski, V. M., Thich, J. A., Solomon, R., and Schugar, H. J. J. Am. Chem. Soc. 1976, 98, 8344-8350
73. Jacobson, R. R., Tyeklár, Z., and Karlin, K. D. Inorg. Chim. Acta 1991, 181, 111-118
74. Lucchese, B., Humphreys, K. J., Lee, D.-H., Incarvito, C. D., Sommer, R. D., Rheingold, A. L., and Karlin, K. D. Inorg. Chem. 2004, 43, 5987-5998
75. Lee, D.-H., Wei, N., Murthy, N. N., Tyeklár, Z., Karlin, K. D., Kaderli, S., Jung, B., and Zuberbühler, A. D. J. Am. Chem. Soc. 1995, 117, 12498-12513
76. Wei, N., Murthy, N. N., Chen, Q., Zubieta, J., and Karlin, K. D. Inorg. Chem. 1994, 33, 1953-1965
77. Wei, N., Murthy, N. N., and Karlin, K. D. Inorg. Chem. 1994, 33, 6093-6100
78. Wei, N., Murthy, N. N., Tyeklár, Z., and Karlin, K. D. Inorg. Chem. 1994, 33, 1177-1183
79. Baldwin, M. J., Ross, P. K., Pate, J. E., Tyeklár, Z., Karlin, K. D., and Solomon, E. I. J. Am. Chem. Soc. 1991, 113, 8671-8679
80. unpublished results.
81. Kunishita, A., Osako, T., Tachi, Y., Teraoka, J., and Itoh, S. Bull. Chem. Soc. Jpn. 2006, 79, 1729-1741
82. Lucas, H. R., Li, L., Sarjeant, A. A. N., Vance, M. A., Solomon, E. I., and Karlin, K. D. J. Am. Chem. Soc. 2009, 131, 3230-3245
83. Henson, M. J., Vance, M. A., Zhang, C. X., Liang, H.-C., Karlin, K. D., and Solomon, E. I. J. Am. Chem. Soc. 2003, 125, 5186-5192