Theoretical study of the N-H tautomerism in free base porphyrin

Journal of Molecular Structure: THEOCHEM

Volumn 390, Issue 1-3, 1997, Pages 149-156

  Boronat, M ^a   Orti E ^a   Viruela, P M ^a   Tomas F ^a  

^a UNIVERSITY OF VALENCIA   (Spain)

Author keywords

Activation energy; Free base porphyrin; Hartree Fock calculation; N H tautomerism; proton transfer mechanism

Indexed keywords

EID: 0042263558     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0166-1280(96)04769-0     Document Type: Article

References (42)

1. K. Smith (Ed.), Porphyrins and Metalloporphyrins, Elsevier, Amsterdam, 1975;
2. D. Dolphin (Ed.), The Porphyrins, Academic Press, New York, 1979;
3. B.D. Berezin, Coordination Compounds of Porphyrins and Phthalocyanines, Wiley, New York, 1981;
4. C.C. Leznoff and B.P. Lever (Eds.), Phthalocyanines: Properties and Applications, VCH, New York, 1989-1994.
5. L.E. Webb and E.B. Fleischer, J. Chem. Phys., 43 (1965) 3100.
6. B.M.L. Chen and A. Tulinsky, J. Am. Chem. Soc., 94 (1972) 4144.
7. J.G. Radziszewski, J. Walulk and J. Michl, Chem. Phys., 136 (1989) 165; J.G. Radziszewski, J. Walulk and J. Michl, J. Mol. Spectrosc., 140 (1990) 373.
8. J.G. Radziszewski, J. Walulk and J. Michl, Chem. Phys., 136 (1989) 165; J.G. Radziszewski, J. Walulk and J. Michl, J. Mol. Spectrosc., 140 (1990) 373.
9. X.-Y. Li and M.Z. Zgierski, J. Phys. Chem., 95 (1991) 4268.
10. J. Braun, M. Schlabach, B. Wehrle, M. Köcher, E. Vogel and H.-H. Limbach, J. Am. Chem. Soc., 116 (1994) 6593.
11. C.B. Storm and Y. Teklu, J. Am. Chem. Soc., 94 (1972) 1745.
12. S.S. Eaton and G.R. Eaton, J. Am. Chem. Soc., 99 (1977) 1601.
13. R.J. Abraham, G.E. Hawkes and K.M. Smith, Tetrahedron Lett., 16 (1974) 1483.
14. J. Hennig and H.-H Limbach, J. Am. Chem. Soc., 106 (1984) 292.
15. L. Frydman, A.C. Oliveri, L.E. Díaz, B. Frydman, F.G. Morin, C.L. Mayne, D.M. Grant and A.D. Adler, J. Am. Chem. Soc., 110 (1988) 336.
16. L. Frydman, A.C. Oliveri, L.E. Díaz, A. Valasinas and B. Frydman, J. Am. Chem. Soc., 110 (1988) 5651.
17. H.-H. Limbach, J. Hennig, R. Kendrick and C.S. Yannoni, J. Am. Chem. Soc., 106 (1984) 4059.
18. B. Wehrle, H.-H. Limbach, M. Köcher, O. Ermer and E. Vogel, Angew. Chem. Int. Ed. Engl., 26 (1987) 934.
19. T. Butenhoff and C.B. Moore, J. Am. Chem. Soc., 110 (1988) 8336.
20. T. Butenhoff, R.S. Chuck, H.-H. Limbach and C.B. Moore, J. Phys. Chem., 94 (1990) 7847.
21. M. Schlabach, H.-H. Limbach, E. Bunnenberg, A.Y.L. Shu, B.-R. Tolf and C. Djerassi, J. Am. Chem. Soc., 115 (1993) 4554; M. Schlabach, B. Wherle, H. Rumpel, J. Braun, G. Scherer and H.-H. Limbach, Ber. Bunsenges. Phys. Chem., 96 (1992) 821.
22. M. Schlabach, H.-H. Limbach, E. Bunnenberg, A.Y.L. Shu, B.-R. Tolf and C. Djerassi, J. Am. Chem. Soc., 115 (1993) 4554; M. Schlabach, B. Wherle, H. Rumpel, J. Braun, G. Scherer and H.-H. Limbach, Ber. Bunsenges. Phys. Chem., 96 (1992) 821.
23. J. Almlöf, T.H. Fischer, P.G. Gassman, A. Ghosh and M. Häser, J. Phys. Chem., 97 (1993) 10964.
24. J.B. Foresman, M. Head-Gordon and J.A. Pople, J. Phys. Chem., 96 (1992) 135.
25. C.H. Reynolds, J. Org. Chem., 53 (1988) 6061.
26. M.J.S. Dewar and M.L. McKee, Pure Appl. Chem., 52 (1980) 1431.
27. R.C. Haddon and H. Raghavachari, J. Am. Chem. Soc., 107 (1985) 289; K. Jug and E. Fasold, J. Am. Chem. Soc., 109 (1987) 2263; J.M. Schulman and R.L. Disch, J. Mol. Struct. (Theochem), 234 (1991) 213.
28. R.C. Haddon and H. Raghavachari, J. Am. Chem. Soc., 107 (1985) 289; K. Jug and E. Fasold, J. Am. Chem. Soc., 109 (1987) 2263; J.M. Schulman and R.L. Disch, J. Mol. Struct. (Theochem), 234 (1991) 213.
29. R.C. Haddon and H. Raghavachari, J. Am. Chem. Soc., 107 (1985) 289; K. Jug and E. Fasold, J. Am. Chem. Soc., 109 (1987) 2263; J.M. Schulman and R.L. Disch, J. Mol. Struct. (Theochem), 234 (1991) 213.
30. M. Merchán, E. Ortí and B.O. Roos, Chem. Phys. Lett., 221 (1994) 136.
31. J.R. Reimers, T.X. Lü, M.L. Crossley and N.S. Hush, J. Am. Chem. Soc., 117 (1995) 2855.
32. A. Ghosh and J. Almlöf, J. Phys. Chem., 99 (1995) 1073.
33. M.J.S. Dewar, E.G. Zoebisch, E.F. Healey and J.J.P. Stewart, J. Am. Chem. Soc., 107 (1985) 3902.
34. J.J.P. Stewart, MOPAC: A General Molecular Orbital Package (Version 6.0), QCPE, 10 (1990) 455.
35. J.W. McIver and A. Komornicki, Chem. Phys. Lett., 10 (1971) 303; J.W. McIver and A. Komornicki, J. Am. Chem. Soc., 94 (1972) 2625.
36. J.W. McIver and A. Komornicki, Chem. Phys. Lett., 10 (1971) 303; J.W. McIver and A. Komornicki, J. Am. Chem. Soc., 94 (1972) 2625.
37. J.S. Binkley, J.A. Pople and W.J. Hehre, J. Am. Chem. Soc., 102 (1980) 939;
38. M.S. Gordon, J.S. Binkley, J.A. Pople, W.J. Pietro and W.J. Hehre, J. Am. Chem. Soc., 104 (1982) 2797.
39. M.J. Frisch, M. Head-Gordon, H.B. Schlegel, K. Raghavachari, J.S. Binkley, C. Gonzalez, D.J. de Frees, D.J. Fox, R.A. Whiteside, R. Seeger, C.F. Melius, J. Baker, R.L. Martin, R.L. Kahn, J.J.P. Stewart, E.M. Fluder, S. Topiol and J.A. Pople, Gaussian 88; Gaussian Inc., Pittsburgh, PA, 1988.
40. K.M. Merz, Jr. and C.H. Reynolds, J. Chem. Soc., Chem. Commun. (1988) 90.
41. Z. Smedarchina, W. Siebrand and F. Zerbetto, Chem. Phys., 136 (1989) 285.
42. M.W. Jurema and G.C. Shields, J. Comput. Chem., 14 (1993) 89.