Structural Consequences of Spin Conversion in a Sterically Encumbered Ni(II) Porphyrin

Journal of Physical Chemistry B

Volumn 103, Issue 41, 1999, Pages 8643-8646

  Barkigia, Kathleen M ^a   Nelson, Nora Y ^b   Renner, Mark W ^a   Smith, Kevin M ^b   Fajer, Jack ^a  

^a BROOKHAVEN NATIONAL LABORATORY   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001609588     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp992508y     Document Type: Article

References (28)

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13. Meunier, B. Chem. Rev. 1992, 92, 1411. Mansuy, D. Coord. Chem. Rev. 1993, 125, 129. Sheldon, R. A. Metalloporphyrins in Catalytic Oxidations; M. Dekker: New York, 1994. Groves, J. T.; Han, Y. Z. In Cytochrome P450: Structure, Mechanism and Biochemistry; Ortiz de Montellano, P., Ed.; Plenum Press: New York, 1995; p 3. Dolphin, D.; Traylor, T. G.; Xie, L. Acc. Chem. Res. 1997, 30, 251. Birnbaum, E. R.; Labinger, J. A.; Bercaw, J. E.; Gray, H. B. Inorg. Chim. Acta 1998, 270, 433. Ozette, K.; Battioni, P.; Leduc, P.; Bartoli, J. F.; Mansuy, D. Inorg. Chim. Acta 1998, 272, 4.
14. Meunier, B. Chem. Rev. 1992, 92, 1411. Mansuy, D. Coord. Chem. Rev. 1993, 125, 129. Sheldon, R. A. Metalloporphyrins in Catalytic Oxidations; M. Dekker: New York, 1994. Groves, J. T.; Han, Y. Z. In Cytochrome P450: Structure, Mechanism and Biochemistry; Ortiz de Montellano, P., Ed.; Plenum Press: New York, 1995; p 3. Dolphin, D.; Traylor, T. G.; Xie, L. Acc. Chem. Res. 1997, 30, 251. Birnbaum, E. R.; Labinger, J. A.; Bercaw, J. E.; Gray, H. B. Inorg. Chim. Acta 1998, 270, 433. Ozette, K.; Battioni, P.; Leduc, P.; Bartoli, J. F.; Mansuy, D. Inorg. Chim. Acta 1998, 272, 4.
15. Meunier, B. Chem. Rev. 1992, 92, 1411. Mansuy, D. Coord. Chem. Rev. 1993, 125, 129. Sheldon, R. A. Metalloporphyrins in Catalytic Oxidations; M. Dekker: New York, 1994. Groves, J. T.; Han, Y. Z. In Cytochrome P450: Structure, Mechanism and Biochemistry; Ortiz de Montellano, P., Ed.; Plenum Press: New York, 1995; p 3. Dolphin, D.; Traylor, T. G.; Xie, L. Acc. Chem. Res. 1997, 30, 251. Birnbaum, E. R.; Labinger, J. A.; Bercaw, J. E.; Gray, H. B. Inorg. Chim. Acta 1998, 270, 433. Ozette, K.; Battioni, P.; Leduc, P.; Bartoli, J. F.; Mansuy, D. Inorg. Chim. Acta 1998, 272, 4.
16. Meunier, B. Chem. Rev. 1992, 92, 1411. Mansuy, D. Coord. Chem. Rev. 1993, 125, 129. Sheldon, R. A. Metalloporphyrins in Catalytic Oxidations; M. Dekker: New York, 1994. Groves, J. T.; Han, Y. Z. In Cytochrome P450: Structure, Mechanism and Biochemistry; Ortiz de Montellano, P., Ed.; Plenum Press: New York, 1995; p 3. Dolphin, D.; Traylor, T. G.; Xie, L. Acc. Chem. Res. 1997, 30, 251. Birnbaum, E. R.; Labinger, J. A.; Bercaw, J. E.; Gray, H. B. Inorg. Chim. Acta 1998, 270, 433. Ozette, K.; Battioni, P.; Leduc, P.; Bartoli, J. F.; Mansuy, D. Inorg. Chim. Acta 1998, 272, 4.
17. Meunier, B. Chem. Rev. 1992, 92, 1411. Mansuy, D. Coord. Chem. Rev. 1993, 125, 129. Sheldon, R. A. Metalloporphyrins in Catalytic Oxidations; M. Dekker: New York, 1994. Groves, J. T.; Han, Y. Z. In Cytochrome P450: Structure, Mechanism and Biochemistry; Ortiz de Montellano, P., Ed.; Plenum Press: New York, 1995; p 3. Dolphin, D.; Traylor, T. G.; Xie, L. Acc. Chem. Res. 1997, 30, 251. Birnbaum, E. R.; Labinger, J. A.; Bercaw, J. E.; Gray, H. B. Inorg. Chim. Acta 1998, 270, 433. Ozette, K.; Battioni, P.; Leduc, P.; Bartoli, J. F.; Mansuy, D. Inorg. Chim. Acta 1998, 272, 4.
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19. 1 may be formally considered to be a porphodimethene. The closest porphodimethene analogue of 1, Ni(II) 5,15-dimethyl-2, 3, 7, 8, 12, 13, 17, 18-octaethyl-5H,15H-porphyrin does not bind axial ligands and adopts a principally roof-like conformation: Dwyer, P. N.; Buchler, J. W.; Scheldt, W. R. J. Am. Chem. Soc. 1974, 96, 2789.
20. Nelson, N. Y.; Medforth, C. J.; Khoury, R. G.; Nurco, D. J.; Smith, K. M. Chem. Commun. 1998, 1687.
21. Drain, C. M.; Gentemann, S.; Roberts, J. A.; Nelson, N. Y.; Medforth, C. J.; Jia, S.; Simpson, M. C.; Smith, K. M.; Fajer, J.; Shelnutt, J. A.; Holten, D. J. Am. Chem. Soc. 1998, 120, 3781.
22. 13
23. 12 two sets of methyl protons (δ 1.74 [d, 12H], 2.11 [s, 12H] and one set of isopropyl methine protons (δ 4.42 [septet, 2H]) which broaden and shift to 0.99 (br, 12H), 4.93 (s, 12H) and -1.33 (br, 2H).
24. The longer Ni-N distances in high-spin F430 likely reflect its more planar conformation compared to that of 2. In contrast, in an isolated low-spin F430, the Ni-N distances average 1.86(2) Å and the molecule is as distorted as 1: Färber, G.; Keller, W.; Kratky, C.; Jaun, B.; Pfaltz, A.; Spinner, C.; Kobelt, A.; Eschenmoser, A. Helv. Chim. Acta 1991, 74, 697.
25. Barkigia, K. M.; Nurco, D. J.; Renner, M. W.; Melamed, D.; Smith, K. M.; Fajer, J. J. Phys. Chem. B 1998, 102, 322.
26. Blake, I. M.; Anderson, H. L.; Beljonne, D.; Bredas, J. L.; Clegg, W. J. Am. Chem. Soc. 1998, 120, 10764.
27. 13 the Ni-N distances average 1.869-(7) Å, essentially the same as those in 1, 1.877(7) Å.
28. Su, W.; Cooper, T. M. Chem. Mater. 1998, 10, 1212.