Synthesis, molecular structures, and properties of six-coordinate [Fe(OEP)(L)(NO)]+ derivatives: Elusive nitrosyl ferric porphyrins

Journal of the American Chemical Society

Volumn 121, Issue 22, 1999, Pages 5210-5219

  Ellison, Mary K ^a   Robert Scheidt, W ^a  

^a UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

IRON DERIVATIVE; NITRIC OXIDE; PORPHYRIN DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; CRYSTALLIZATION; INFRARED SPECTROMETRY; NONHUMAN; ULTRAVIOLET SPECTROPHOTOMETRY;

EID: 0345517351     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja984308q     Document Type: Article

References (65)

1. (a) Ribeiro, J. M. C.; Hazzard, J. M. H.; Nussenzveig, R. H.; Champagne, D. E.; Walker, F. A. Science 1993, 260, 539.
2. (b) Anderson, J. F.; Champagne, D. E.; Weichsel, A.; Ribeiro, J. M. C.; Balfour, C. A.; Dress, V.; Montfort, W. R. Biochemistry 1997, 36, 4423.
3. Valenzuela, J. G.; Walker, F. A.; Ribeiro, J. M. C. J. Exp. Biol. 1995, 198, 1519.
4. Averill, B. A. Chem. Rev. 1996, 96, 2951 and references therein.
5. Williams, P. A.; Fülöp, V.; Garman, E. F.; Saunders, N. F. W.; Ferguson, S. J.; Hajdu, J. Nature 1997, 389, 406.
6. Obayashi, E.; Tsukamoto, K.; Adachi, S.; Takahashi, S.; Nomura, M.; Iizuka, T.; Shoun, H.; Shiro, Y. J. Am. Chem. Soc. 1997, 119, 7807.
7. Wang, Y.; Averill, B. A. J. Am. Chem. Soc. 1996, 118, 3972.
8. Fülöp, V.; Moir, J. W. B.; Ferguson, S. J.; Hajdu, J. Cell 1995, 81, 369.
9. Enemark, J. H.; Feltham, R. D. Coord. Chem. Rev. 1974, 13, 339.
10. Westcott, B. L.; Enemark; J. H. In Inorganic Electronic Structure and Spectroscopy; Lever, A. B. P., Solomon, E. I., Eds.; in press.
11. (a) Wayland, B. B.; Olson, L. W. J. Am. Chem. Soc. 1974, 96, 6037.
12. (b) Olson, L. W.; Schaeper, D.; Lançon, D.; Kadish, K. M. J. Am. Chem. Soc. 1982, 104, 2042.
13. (c) Lançon, D.; Kadish, K. M. J. Am. Chem. Soc. 1983, 105, 5610.
14. (d) Fujita, E.; Fajer, J. J. Am. Chem. Soc. 1983, 106, 6743.
15. (e) Yoshimura, T. Inorg. Chim. Acta 1984, 83, 17.
16. (f) Settin, M. F.; Fanning, J. C. Inorg. Chem. 1988, 27, 1431.
17. (g) Mu, X. H.; Kadish, K. M. Inorg. Chem. 1988, 27, 4720.
18. (h) Hoshino, M.; Ozawa, K.; Seki, H.; Ford, P. C. J. Am. Chem. Soc. 1993, 115, 9568.
19. (i) Ozawa, S.; Sakamoto, E.; Ichikawa, T.; Watanabe, Y.; Morishima, I. Inorg. Chem. 1995, 34, 6362.
20. Scheidt, W. R.; Lee, Y. J.; Hatano, K. J. Am. Chem. Soc. 1984, 106, 3191.
21. Yi, G.-B.; Chen, L.; Khan, M. A.; Richter-Addo, G. B. Inorg. Chem. 1997, 36, 3876.
22. Dodd, R. E.; Robinson, P. L. Experimental Inorganic Chemistry; Elsevier: New York, 1957; pp 233-234.
23. 2Py, 4-(dimethylamino)-pyridine; 3-ClPy, 3-chloropyridine; 1-VinIm, 1-vinylimidazole; 1-BzlIm, 1-benzylimidazole; Pip, piperidine; Np, porphyrinato nitrogen.
24. (a) Adler, A. D.; Longo, F. R.; Kampus, F.; Kim, J. J. Inorg. Nucl. Chem. 1970, 32, 2443.
25. (b) Buchler, J. W. In Porphyrins and Metalloporphyrins; Smith, K. M., Ed.; Elsevier Scientific Publishing: Amsterdam, The Netherlands, 1975; Chapter 5.
26. Dolphin, D. H.; Sams, J. R.; Tsin, T. B. Inorg. Chem. 1977, 16, 711.
27. Wolsey, W. C. J. Chem. Educ. 1973, 50, A335; Chem. Eng. News 1983, 61 (Dec. 5), 4; 1963, 41 (July 8), 47.
28. Wolsey, W. C. J. Chem. Educ. 1973, 50, A335; Chem. Eng. News 1983, 61 (Dec. 5), 4; 1963, 41 (July 8), 47.
29. Wolsey, W. C. J. Chem. Educ. 1973, 50, A335; Chem. Eng. News 1983, 61 (Dec. 5), 4; 1963, 41 (July 8), 47.
30. Scheidt, W. R.; Turowska-Tyrk, I. Inorg. Chem. 1994, 33, 1314.
31. Sheldrick, G. M. Acta Crystallogr. 1990, A46, 467.
32. Sheldrick, G. M. J. Appl. Cryst., manuscript in preparation.
33. 2) are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.
34. 23 logic to area detector geometry by Karaulov: Karaulov, A. I.; School of Chemistry and Applied Chemistry, University of Wales, College of Cardiff, Cardiff CF1 3TB, UK, personal communication.
35. Walker, N. P.; Stuart, D. Acta Crystallogr., Sect. A 1983, A39, 158.
36. Ellison, M. K.; Schulz, C. E.; Scheidt, W. R. Inorg. Chem. 1999, 38, 100.
37. Scheidt, W. R.; Frisse, M. E. J. Am. Chem. Soc. 1975, 97, 17.
38. Ellison, M. K.; Scheidt, W. R. J. Am. Chem. Soc. 1997, 119, 7404.
39. Piciulo, P. L.; Scheidt, W. R. J. Am. Chem. Soc. 1976, 98, 1913.
40. Scheidt, W. R.; Brinegar, A. C.; Ferro, E. B.; Kirner, J. F. J. Am. Chem. Soc. 1977, 99, 7315.
41. Higgins, T. B.; Safo, M. K.; Scheidt, W. R. Inorg. Chim. Acta 1990, 178, 261.
42. Little, R. G.; Dymock, K. R.; Ibers, J. A. J. Am. Chem. Soc. 1975, 97, 4532.
43. Safo, M. K.; Gupta, G. P.; Walker, F. A.; Scheidt, W. R. J. Am. Chem. Soc. 1991, 113, 5497.
44. Inniss, D.; Soltis, S. M.; Strouse, C. E. J. Am. Chem. Soc. 1988, 110, 5644.
45. Safo, M. K.; Walker, F. A.; Raitsimring, A. M; Walters, W. P.; Dolata, D. P.; Debrunner, P. G.; Scheidt, W. R. J. Am. Chem. Soc. 1994, 116, 7760.
46. Scheidt, W. R.; Geiger, D. K.; Haller, K. J. J. Am. Chem. Soc. 1982, 104, 495.
47. Safo, M. K.; Scheidt, W. R.; Gupta, G. P. Inorg. Chem. 1990, 29, 626.
48. (a) Steffen, W. L.; Chun, H. K.; Hoard, J. L.; Reed, C. A. Abstracts of Papers, 175th National Meeting of the American Chemical Society, Anaheim, CA, March 13-17, 1978; American Chemical Society: Washington, DC, 1978; INOR 15.
49. (b) Hoard, J. L., personal communication.
50. Radonovich, L. J.; Bloom, A.; Hoard, J. L. J. Am. Chem. Soc. 1972, 94, 2073.
51. Hiller, W.; Hanack, M.; Mezger, M. G. Acta Crystallogr., Sect. C 1987, C43, 1264.
52. See, for example, Table II of reference 10h and references cited therein.
53. Atwood, J. D. Inorganic and Organometallic Reaction Mechanisms; Brooks/Cole Publishing Co.: Monterey, CA, 1985; pp 51-55.
54. 4v saucering of the four pyrrole rings such that the perpendicular displacements of the β-carbon atoms are more displaced from the mean 24-atom plane than the α-carbons or the nitrogen atoms. These displacements are in the direction away from the central metal and represent the usual case (see Figure S3). Reverse doming is a relatively infrequently occurring core conformation in which the pattern of displacements of the β-carbon atoms and the α-carbon or nitrogen atoms are reversed. Thus, in this case the N-atoms and α-carbons are displaced out of the 24-atom mean plane away from the metal, and the β-carbons are displaced towards the metal.
55. 2 there is one β-carbon atom (Cb8) which is disordered over two positions (above and below the plane) with nearly equivalent populations. For this case the mean plane was calculated by using both atom coordinates. However, the calculation based on only the 23 ordered atoms gave essentially the same results.
56. Scheidt, W. R.; Reed, C. A. Chem.. Rev. 1981, 81, 543.
57. Scheidt, W. R.; Lee, Y. J. Struct. Bonding (Berlin) 1987, 64, 1-70.
58. (a) Shiro, Y.; Fujii, M.; Iizuka, T.; Adachi, S.; Tsukamoto, K.; Nakahara, K.; Shoun, H. J. Biol. Chem. 1995, 270, 1617.
59. (b) Yoshimura, T.; Fujii, S.; Kamada, H.; Yamaguchi, K.; Suzuki, S.; Shidara, S.; Takakuwa, S. Biochim. Biophys. Acta 1996, 1292, 39.
60. (a) Stolzenberg, A. M.; Strauss, S. H.; Holm, R. H. J. Am. Chem. Soc. 1981, 103, 4763.
61. (b) Rougee, M.; Brault, D. Biochemistry 1975, 14, 4100.
62. (c) Wang, C.-M.; Brinigar, W. S. Biochemistry 1979, 18, 4960.
63. Guilard, R.; Lagrange, G.; Tabard, A.; Lançon, D.; Kadish, K. M. Inorg. Chem. 1985, 24, 3649.
64. 49
65. Ellison, M. K.; Scheidt, W. R., unpublished structural observations.