X-ray structures and homolysis of some alkylcobalt(III) phthalocyanine complexes

Inorganic Chemistry

Volumn 44, Issue 26, 2005, Pages 9902-9913

  Galezowski, Wlodzimierz ^a   Kubicki, Maciej ^a  

^a ADAM MICKIEWICZ UNIVERSITY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 31144459324     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic051078p     Document Type: Article

References (100)

1. 2′-propanediylbis(2,3-butanedione 2-imine-3-oxime); salen, dianion of bis(salicydene)ethylenediamine; saloph, dianion of bis(salicylidene)-o-phenylenediamine; TC, tropocoronand; acacen, dianion of bis(acetylacetone)ethylenediimine; py, pyridine; N-MeIm, N-methylimidazole; DMA, dimethylacetamide; DMSO, dimethyl sulfoxide; TEMPO, 2,2,6,6-tetramethyl-1-piperidinyloxy.
2. Brückner, S.; Calligaris, M.; Nardin, G.; Randaccio, L. Inorg Chim. Acta 1969, 3, 308.
3. Summers, M. F.; Marzilli, L. G.; Bresciani-Pahor, N.; Randaccio, L. J. Am. Chem. Soc. 1984, 106, 4478.
4. Parker, W. O., Jr.; Bresciani-Pahor, N.; Zangrando, E.; Randaccio, L.; Marzilli, L. G. Inorg. Chem. 1985, 24, 3908.
5. Jaynes, B. S.; Ren, T.; Masschelein, A.; Lippard, S. J. Am. Chem. Soc. 1993, 115, 5589.
6. Summers, J. S.; Petersen, J. L.; Stolzenberg, A. M. J. Am. Chem. Soc. 1994, 111, 7189.
7. Cao, Y.; Stolzenberg, A. M.; Petersen, J. L. Inorg. Chim. Acta 1997, 263, 139.
8. Cobalamins seem to be a natural reference point here.
9. Galezowski, W. Inorg. Chem. 2005, 44, 1530.
10. In solution, even in nonbinding solvents, the complexes are monomeric (see ref 9).
11. Stuzhin, P. A.; Khelevina, O. G.; Berezin, B. D. In Phthalocyanines. Properties and Applications; Leznoff, C. C., Lever A. B. P., Eds.; Wiley-VCH: New York, 1996; Vol. 4, Chapter 2.
12. Lever, A. B. P.; Milaeva, E. R.; Speier, G. In Phthalocyanines. Properties and Applications; Leznoff, C. C., Lever A. B. P., Eds.; Wiley-VCH: New York, 1993; Vol. 3, Chapter 1, p 47.
13. Zhou, D.-L.; Gao, J.; Rusling, J. F. J. Am. Chem. Soc. 1995, 117, 1127.
14. Sirovatka, J. M.; Rappé, A. K.; Finke, R. G. Inorg. Chim. Acta. 2000, 300-302, 545.
15. (b) Brown, K. L.; Marques, H. M. J. Inorg. Biochem. 2001, 83, 121.
16. Jensen, K. P.; Ryde, U. J. Phys. Chem. A 2003, 107, 7539.
17. (b) Jensen, K. P.; Ryde, U. THEOCHEM 2002, 585, 239.
18. (c) Jensen, K. P.; Sauer, S. P. A.; Liljefors, T.; Norrby, P.-O. Organometallics 2001, 20, 550.
19. (d) Friendorf, M.; Kozlowski, P. M. J. Am. Chem. Soc. 2004, 126, 1928.
20. (e) Andriuniow, T.; Zgierski, M. Z.; Kozlowski, P. M. J. Am. Chem. Soc. 2001, 123, 2679.
21. (f) Andriuniow, T.; Zgierski, M. Z.; Kozlowski, P. M. J. Phys. Chem. B 2000, 104, 10921.
22. (g) Dölker, N.; Maseras, F.; Lledós, A. J. Phys. Chem. B 2003, 107, 306.
23. Riordan, C. G.; Halpern, J. Inorg. Chim. Acta 1996, 243, 19.
24. Qiu, A.; Sawyer, D. T. J. Porphyrins Phthalocyanines 1997, 1, 125.
25. Martin, B. D.; Finke, R. G. J. Am. Chem. Soc. 1992, 114, 585.
26. Toscano, P. J.; Seligson, A. L.; Curran, M. T.; Skrobutt, A. T.; Sonnenberger, D. C. Inorg. Chem. 1989, 28, 166.
27. Fukuzumi, S.; Miyamoto, K.; Suenobu, T.; Van Caemelbecke, E.; Kadish, K. M. J. Am. Chem. Soc. 1998, 120, 2880.
28. Galezowski, W.; Ibrahim, P. N.; Lewis, E. S. J. Am. Chem. Soc. 1993, 115, 8660.
29. See eq 12 in Marcus, R. A. J. Phys. Chem. A 1997, 101, 4072.
30. Geno, M. K.; Halpern, J. J. Am. Chem. Soc. 1987, 109, 1238.
31. Kaplan, W. A.; Scott, R. A.; Suslick, K. S. J. Am. Chem. Soc. 1990, 112, 1283.
32. IIIPc to be obtained.
33. CrysAlisCCD, version 171; Oxford Diffraction Poland Sp.: Wroclaw, Poland, 2003.
34. Blessing, R. H. J. Appl. Crystallgr. 1989, 22, 396.
35. Sheldrick, G. M. Acta Crystallogr. 1990, A46, 467.
36. Sheldrick, G. M. SHELXL-97, Program for the Refinement of Crystal Structures; University of Göttingen: Göttingen, Germany, 1997.
37. Kendrick, M. J.; Al-Akhdar, W. Inorg. Chem. 1987, 26, 3792.
38. Mason, R.; Williams, G. A.; Fielding, P. E. J. Chem. Soc., Dalton Trans. 1979, 676.
39. Williams, G. A.; Figgis, B. N.; Mason, R.; Mason, S. A.; Fielding, P. E. J. Chem. Soc., Dalton Trans. 1980, 1688.
40. Figgis, B. N.; Kucharski, E. S.; Reynolds, P. A. J. Am. Chem. Soc. 1989, 111, 1683.
41. Janczak, J.; Kubiak, R. Inorg. Chim. Acta 2003, 342, 64.
42. Little, R. G.; Ibers, J. A. J. Am. Chem. Soc. 1974, 96, 4440.
43. Calligaris, M.; Minichelli, D.; Nardin, G.; Randaccio, L. J. Chem. Soc. A 1971, 2722.
44. Reynolds, P. A.; Figgis, B. N. Inorg. Chem. 1991, 30, 2294.
45. Liao, M.-S.; Watts, J. D.; Huang, M.-J. Inorg. Chem. 2005, 44, 1941 and references therein.
46. Heuts, J. P. A.; Schipper, E. T. M. W.; Piet, P.; German, A. L. J. Mol. Struct. 1995, 333, 39 and references therein.
47. Gacho, E. H.; Naito, T.; Inabe, T.; Fukuda, T.; Kobayashi, N. Chem. Lett. 2001, 260.
48. Ballirano, P.; Caminiti, R.; Ercolani, C.; Maras, A.; Orru, M. A. J. Am. Chem. Soc. 1998, 120, 12798.
49. 2 dimer N atoms of the phthalocyanine moiety are not even the closest contacts of the central metal atoms. Fischer, M. S.; Templeton, D. H.; Zalkin, A.; Melvin, C. J. Am. Chem. Soc. 1971, 93, 2622.
50. IIPc(N- donor) complexes are known.
51. Bigotto, A.; Zangrando, E.; Randaccio, L. J. Chem. Soc., Dalton Trans. 1976, 96.
52. Calligaris, M.; Nardin, G.; Randaccio, L. Inorg. Nucl. Chem. Lett. 1972, 8, 477.
53. Randaccio, L.; Furlan, M.; Geremia, S; Slouf, M.; Srnova, I.; Toffoli, D. Inorg. Chem. 2000, 38, 3403.
54. Zou, X.; Brown, K. L. Inorg. Chim. Acta 1998, 267, 305.
55. Ouyang, L.; Rulis, P.; Ching, W. Y.; Nardin, G.; Randaccio, L. Inorg. Chem. 2004, 43, 1235.
56. 3Cbl (Table 6) appears to be significant, 0.22 Å.
57. Kastner, M. E.; Scheidt, W. R. J. Organomet. Chem. 1978, 157, 109.
58. Marzilli, L. G.; Summers, M. F.; Bresciani-Pahor, N.; Zangrando, E.; Charland, J.-P.; Randaccio, L. J. Am. Chem. Soc. 1985, 107, 6880.
59. Marzilli, L. G.; Summers, M. F.; Zangrando, E.; Bresciani-Pahor, N.; Randaccio, L. J. Am. Chem. Soc. 1986, 108, 4830.
60. The comparison is meaningful because of the similar steric requirements of the two complexes, at least in the vicinity of the Co center.
61. Doerrer, L. H.; Bautista, M. T.; Lippard, S. J. Inorg. Chem. 1997, 36, 3578.
62. 3 (ref 51b).
63. 3Co(OEP)py structure the extent of this expansion is less certain.
64. Galezowski, W. Inorg. Chem. 2005, 44, 5483.
65. Parker, W. O., Jr.; Zangrando, E.; Bresciani-Pahor, N.; Marzilli, P. A.; Randaccio, L.; Marzilli, L. G. Inorg. Chem. 1988, 27, 2170.
66. +/Fc of 0.5 V is assumed (see ref 12).
67. Stadlauber, E. A.; Holland, R. J.; Lamm, F. P.; Schrauzer, G. N. Bioinorg. Chem. 1974, 4, 67.
68. (b) A rather extreme view that alkylcobalt(III) complexes have considerable Co(I) character has been presented in Andriuniow, T.; Zgierski, M. Z.; Kozlowski, P. M. J. Phys. Chem. B 2000, 104, 10921
69. and also in (c) De Ridder, D. J. A.; Zangrando, E., Bürgi, H.-B. J. Mol. Struct. 1996, 474, 63.
70. 3 and +0.54 on Co.
71. Terazono, Y.; Patrick, B. O.; Dolphin, D. H. Inorg. Chim. Acta 2003, 346, 265.
72. Scheidt, W. R.; Ramanuja, J. A. Inorg. Chem. 1975, 14, 2643.
73. Stolzenberg, A. M.; Cao, Y. J. Am. Chem. Soc. 2001, 123, 9078.
74. Tsou, T.-T.; Loots, M.; Halpern, J. J. Am. Chem. Soc. 1982, 104, 623 and references therein.
75. Kim, S. H.; Chen, H. L.; Feilchenfeld, N.; Halpern, J. J. Am. Chem. Soc. 1988, 110, 3120.
76. Garr, C. D.; Finke, R. G. J. Am. Chem. Soc. 1992, 114, 10440.
77. - solution.
78. Electron transfer from the ethyl radical to Co(II)Pc followed by deprotonation of ethyl cation is also conceivable.
79. A reaction similar to the formation of a yellow decay product in DMF observed by others: Rollmann, D.; Iwamoto, R. T. J. Am. Chem. Soc. 1968, 90, 1455.
80. The reduction potential of TEMPO is -0.15 V vs SCE: Finke, R. G.; Smith, B. L.; Mayer, B. J.; Molinero, A. A. Inorg. Chem. 1983, 25, 3677 and references therein.
81. - by the trap. Oxidative properties of TEMPO were also discussed in Samsel, E.; Kochi, J. J. Am. Chem. Soc. 1986, 108, 4790.
82. Halpern, J. Pure Appl. Chem. 1983, 33, 1059.
83. 1 ratio was observed by Halpern and co-workers, see ref 66.
84. Garr, C. D.; Finke, R. G. Inorg. Chem. 1993, 32, 4412.
85. Hung, R. R.; Grabowski, J. J. J. Am. Chem. Soc. 1999, 121, 1359.
86. BF > 36 kcal/mol).
87. Nie, S.; Marzilli, P. A.; Marzilli, L. G.; Yu, N.-T. J. Am. Chem. Soc. 1990, 112, 6084 and references therein.
88. Riordan, C. G.; Halpern, J. Inorg. Chim. Acta 1996, 243, 19.
89. Ng, F. T. T.; Rempel, G. L.; Halpern, J. J. Am. Chem. Soc. 1982, 104, 621.
90. IIIPc.
91. Summers, M. F.; Toscano, P. J.; Bresciani-Pahor, N.; Nardin, G.; Randaccio, L.; Marzilli, L. G. J. Am. Chem. Soc. 1983, 105, 6259.
92. In an enzymatic environment, in the absence of diffusion step, there is probably no transition state. Brown, K. L.; Marques, H. M. THEOCHEM 2005, 714, 209.
93. Berendsen, H. J. C.; Postma, J. P. M.; Van Gunsteren, W. F.; DiNicola, A.; Haak, J. R. J. Chem. Phys. 1984, 81, 3684.
94. (b) Kräutler, B.; Keller, W.; Kratky, C. J. Am. Chem. Soc. 1989, 111, 8936.
95. Stolzenberg, A. M.; Summers, J. S. Inorg. Chem. 2000, 39, 1518.
96. Kadish, K. M.; Han, B. C.; Endo, A. Inorg. Chem. 1991, 30, 4502.
97. Kadish, K. M.; Botomley, L. A.; Beroiz, D. Inorg. Chem. 1978, 17, 1124.
98. 4] complexes, R = tert-butyl or neo-pentoxyl. Galezowski, W. Unpublished results.
99. Kimura, M.; Sakaguchi, A.; Ohtha, K.; Hanabusa, K.; Shirai, H.; Kobayashi, N. Inorg. Chem. 2003, 42, 2821.
100. It should be noted, however, that it has been claimed that the BDE for benzyl-Co(OEP)(L) varies with the basicity of the trans ligand within several kcal/mol (see ref 23).