A comparison of ortho, meta, and para substituent effects in tetraphenylporphyrins: Insights into the nature of the porphyrin-phenyl electronic interaction

Journal of Molecular Structure: THEOCHEM

Volumn 388, Issue 1-3, 1996, Pages 359-363

  Ghosh, Abhik ^a  

^a UNIVERSITY OF TROMSØ   (Norway)

Author keywords

Electron withdrawing substituent; Porphyrin phenyl interaction; Substituent effect; Tetraphenylporphyrin

Indexed keywords

EID: 0010385650     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/s0166-1280(96)04720-3     Document Type: Review

References (25)

1. A. Ghosh, J. Am. Chem. Soc., 117 (1995) 4691.
2. T.G. Traylor and S. Tsuchiya, Inorg. Chem., 26 (1987) 1338.
3. T. Wijesekera, A. Matsumoto, D. Dolphin and D. Lexa, Angew. Chem. Int. Ed. Engl., 29 (1990) 1028.
4. See, e.g., J.A. Hodge, M.G. Hill and H.B. Gray, Inorg. Chem., 34 (1995) 809.
5. P.G. Gassman, A. Ghosh and J. Almlöf, J. Am. Chem. Soc., 114 (1992) 9990.
6. A. Ghosh, J. Org. Chem., 58 (1993) 6932.
7. A. Ghosh, P.G. Gassman and J. Almlöf, J. Am. Chem. Soc., 116 (1994) 1932.
8. A. Ghosh, J. Fitzgerald, P.G. Gassman and J. Almlöf, Inorg. Chem., 33 (1994) 6057.
9. For a recent paper that can serve as an introduction to porphyrin cation radicals, see C.M. Barzilay, S.A. Sibilia, T.G. Spiro and Z. Gross, Chem. Eur. J., 1 (1995) 222.
10. B. Delley, J. Chem. Phys., 92 (1990) 508.
11. U. von Barth and L. Hedin, J. Phys. C, 5 (1972) 1629.
12. For details see DMol User Guide, available from Biosym Technologies, Inc., 9685 Scranton Road, San Diego, CA 92121-2777.
13. P. Dupuis, R. Roberge and C. Sandorfy, Chem. Phys. Lett., 75 (1980) 434.
14. S. Kitagawa, I. Morishima, T. Yonezawa and N. Sato, Inorg. Chem., 18 (1979) 1345.
15. C. Khandelwal and J.L. Roebber, Chem. Phys. Lett., 34 (1975) 355.
16. A. Ghosh, J. Almlöf and P.G. Gassman, Chem. Phys. Lett., 186 (1991) 113.
17. A. Ghosh and J. Almlöf, Chem. Phys. Lett., 213 (1993) 519.
18. A. Ghosh, J. Phys. Chem., 98 (1994) 11004.
19. This compound has been prepared, but its electrochemical properties have not been reported: C.A. Quintana, R.A. Assink and J.A. Shelnutt, Inorg. Chem., 28 (1989) 3429.
20. 2 on the porphyrin core are currently not as well understood as the effects of electron-withdrawing substituents. Electrochemical one-electron oxidation potentials of tetrakis-para-substituted tetraphenylporphyrins show good correlations with Hammett σ constants for electron-withdrawing para substituents. But the reaction constant p thus obtained does not reproduce the experimentally measured oxidation potentials for tetraphenylporphyrins with strongly electron-donating para substituents.
21. D.J. Byron, G.W. Gray and R.C. Wilson, J. Chem. Soc. C, (1966) 837.
22. K. Bowden and M. Hojatti, J. Chem. Soc. Perkin Trans. 2, (1990) 1201.
23. K. Bowden and E.J. Grubbs, Prog. Phys. Org. Chem., 19 (1993) 183.
24. R.A. Sheldon (Ed.), Metalloporphyrins in Catalytic Oxidations, Marcel Dekker, New York, 1994.
25. F. Montanari and L. Casella (Eds.), Metalloporphyrins Catalyzed Oxidations, Kluwer Academic, Dordrecht, 1994.