Russian Journal of General Chemistry

, Volume 78, Issue 4, pp 784–792 | Cite as

Acid properties of porphyrins and related systems

Article

Abstract

Structural, energetic, and electronic aspects of a series of porphyrins and related compounds in their neutral, anion, and dianion electronic states have been studied by means of DFT calculations [B3LYP/6-31+G(d,p)]. Analysis of the electron density puts forward a number of different kinds of interactions between the inner atoms. Intramolecular correlations similar to those found in intermolecular N-H···N interactions have been found.

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References

  1. 1.
    Sessler, J.L. and Weghorn, S.J.: Expanded, Contracted & Isomeric Porphyrins, New York: Pergamon, 1997.Google Scholar
  2. 2.
    Kadish, K. M., Smith, K. M., and Guilard, R, The Porphyrin Handbook, San Diego: Academic, 1999.Google Scholar
  3. 3.
    Lacerda, P.S.S., Silva, A.M.G., Tome, A.C., Neves, M.G.P.M.S., Silva, A.M.S., Cavaleiro, J.A. S., and Llamas—Saiz. A. L., Angew. Chem. Int. Ed., 2006, vol. 45, no. 33, p. 5487.CrossRefGoogle Scholar
  4. 4.
    Torres, T., Angew. Chem. Int. Ed., 2006, vol. 45, no. 18, p. 2834.CrossRefGoogle Scholar
  5. 5.
    Rodríguez—Morgade, M.S., Claessens, C.G., Medina, A., González—Rodríguez, D., Gutiérrez—Puebla, E., Monge, A., Alkorta, I., and Torres, T., J. Am. Chem. Soc., 2007, in press.Google Scholar
  6. 6.
    Ulman, A. and Manassen, J., J. Am. Chem. Soc., 1975, vol. 97, no. 22, p. 6540.CrossRefGoogle Scholar
  7. 7.
    Stilts, C.E., Nelen, M.I., Hilmey, D.G., Davies, S.R., Gollnick, S.O., Oseroff, A.R., Gibson, S.L., Hilf, R., and Detty, M.R., J. Med. Chem., 2000, vol. 43, no. 12, p. 2403.CrossRefGoogle Scholar
  8. 8.
    Abe, M., Hilmey, D.G., Stilts, C.E., Sukumaran, D.K., and Detty, M. R., Organometallics, 2002, vol. 21, no. 14, p. 2986.CrossRefGoogle Scholar
  9. 9.
    Abe, M., You, Y., and Detty, M. R., Ibid., 2002, vol. 21, no. 21, p. 4546.CrossRefGoogle Scholar
  10. 10.
    Langer, U., Hoelger, C., Wehrle, B., Latanowicz, L., Vogel, E., and Limbach, H. H., J. Phys. Org. Chem., 2000, vol. 13, no. 1, p. 23.CrossRefGoogle Scholar
  11. 11.
    Pukhovskaya, S.G., Guseva, L. Z., Malkova, O.V., Semeikin, A.S., and Golubchikov, O. A., Russ. J. Gen. Chem., 2003, vol. 73, no. 3, p. 473.CrossRefGoogle Scholar
  12. 12.
    Winnischofer, H., Engelmann, F.M., Toma, H.E., Araki, K., and Rechenberg, H.R., Inorg Chim. Acta, 2002, vol. 338, no. p. 27.CrossRefGoogle Scholar
  13. 13.
    Araki K., Winnischofer, H., Toma, H. E., Maeda, H., Osuka, A., and Furuta, H., Inorg. Chem., 2001, vol. 40, no. 9, p. 2020.CrossRefGoogle Scholar
  14. 14.
    Mamardashvili, N.Z., Ivanova, Y.B., Sheinin, V.B., Golubchikov, O.A., and Berezin, B.D., Russ. J. Gen. Chem., 2001, vol. 71, no. 5, p. 797.CrossRefGoogle Scholar
  15. 15.
    Khelevina, O.G., Rumyantseva, S.V., Chizhova, N. V., Stuzhin, P.A., and Migalova, I.S., Russ. J. Gen. Chem., 2003, vol. 73, no. 3, p. 478.CrossRefGoogle Scholar
  16. 16.
    Khelevina, O.G., Rumyantseva, S.V., Kulinich, V. P., and Shaposhnikov, G. P., Russ. J. Gen. Chem., 2003, vol. 73, no. 2, p. 288.CrossRefGoogle Scholar
  17. 17.
    Khelevina, O.G., Bubnova, A.S., and Makarova, O. N., Russ. J. Gen. Chem., 2006, vol. 76, no. 9, p. 1504.CrossRefGoogle Scholar
  18. 18.
    Khelevina, O.G., Ferro, V.R., Islyaikin, M.K., Veselkova, E.A., Stryapan, M.G., and de la Vega, J.M.G., J. Phys. Org. Chem., 2005, vol. 18, no. 4, p. 329.CrossRefGoogle Scholar
  19. 19.
    Braun, J., Hasenfratz, C., Schwesinger, R., and Limbach, H. H., Angew. Chem. Int. Ed., 1994, vol. 33, no. 21, p. 2215.CrossRefGoogle Scholar
  20. 20.
    Schroeder, G., Brzezinski, B., Podebski, D., and Grech, E., J. Mol. Struct., 1997, vol. 416, nos. 1–3, p. 11.CrossRefGoogle Scholar
  21. 21.
    Claramunt, R. M., Elguero, J., and Katritzky, A.R., Adv. Heterocycl. Chem., 2000, vol. 77, no. 1, p. 1.CrossRefGoogle Scholar
  22. 22.
    Clarke, J. A., Dawson, P. J., Grigg, R., and Rochester, Ch., J. Chem. Soc. Perkin Trans. 2, 1973, no. 4, p. 414.Google Scholar
  23. 23.
    Kadish, K. M., Smith, K. M., and Guilard, R, The Porphyrin Handbook, San Diego: Academic, 1999, vol. 7, ch. 47.Google Scholar
  24. 24.
    Almlof, J., Fischer, T. H., Gassman, P. G., Ghosh, A., and Haser, M., J. Phys. Chem., 1993, vol. 97, no. 42, p. 10964.CrossRefGoogle Scholar
  25. 25.
    Ghosh, A., J. Phys. Chem. B, 1997, vol. 101, no. 16, p. 3290.CrossRefGoogle Scholar
  26. 26.
    Punnagai, M. and Sastry, G. N., J. Mol. Struct. (Theochem), 2004, vol. 684, nos. 1–3, p. 21.CrossRefGoogle Scholar
  27. 27.
    Punnagai, M., Sateesh, B., and Sastry, G.N., Arkivoc, 2005, vol. 3, p. 258.Google Scholar
  28. 28.
    Punnagai, M., Joseph, S., and Sastry, G.N., J. Chem. Sci., 2004, vol. 116, no. 5, p. 271.CrossRefGoogle Scholar
  29. 29.
    Wu, Y.D., Chan, K.W.K., Yip, C.P., Vogel, E., Plattner, D.A., and Houk, K.N., J. Org. Chem., 1997, vol. 62, no. 26, p. 9240.CrossRefGoogle Scholar
  30. 30.
    Baker, J., Kozlowski, P.M., Jarzecki, A.A., and Pulay, P., Theor. Chem. Acc., 1997, vol. 97, nos. 1–4, p. 59.Google Scholar
  31. 31.
    Reimers, J.R., Lu, T.X., Crossley, M.J., and Hush, N. S., J. Am. Chem. Soc., 1995, vol. 117, no. 10, p. 2855.CrossRefGoogle Scholar
  32. 32.
    Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Zakrzewski, V.G., Montgomery, J.A., Stratmann, R.E., Burant, J.C., Dapprich, S., Millam, J. M., Daniels, A.D., Kudin, K. N., Strain, M. C., Farkas, O., Tomasi, J., Barone, V., Cossi, M., Cammi, R., Mennucci, B., Pomelli, C., Adamo, C., Clifford, S., Ochterski, J., Petersson, G. A., Ayala, P. Y., Cui, Q., Morokuma, K., Malick, D.K., Rabuck, A.D., Raghavachari, K., Foresman, J.B., Cioslowski, J., Ortiz, J. V., Stefanov, B. B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Gomperts, R., Martin, R.L., Fox, D.J., Keith, T., Al-Laham, M.A., Peng, C.Y., Nanayakkara, A., Gonzalez, C., Challacombe, M., Gill, P.M.W., Johnson, B.G., Chen, W., Wong, M.W., Andres, J.L., Head-Gordon, M., Replogle, E.S., and Pople, J.A., Gaussian-98, Pittsburgh, PA: Gaussian, 1998.Google Scholar
  33. 33.
    Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Montgomery, J. J. A., Vreven, T., Kudin, K. N., Burant, J. C., Millam, J. M., Iyengar, S.S., Tomasi, J., Barone, V., Mennucci, B., Cossi, M., Scalmani, G., Rega, N., Petersson, G.A., Nakatsuji, H., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Klene, M., Li, X., Knox, J. E., Hratchian, H. P., Cross, J. B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Ayala, P. Y., Morokuma, K., Voth, G.A., Salvador, P., Dannenberg, J.J., Zakrzewski, V.G., Dapprich, S., Daniels, A.D., Strain, M.C., Farkas, O., Malick, D.K., Rabuck, A.D., Raghavachari, K., Foresman, J.B., Ortiz, J.V., Cui, Q., Baboul, A.G., Clifford, S., Cioslowski, J., Stefanov, B.B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Martin, R. L., Fox, D. J., Keith, T., Al-Laham, M.A., Peng, C.Y., Nanayakkara, A., Challacombe, M., Gill, P.M.W., Johnson, B., Chen, W., Wong, M.W., Gonzalez, C., and Pople, J.A., Gaussian-03, Wallingford, CT: Gaussian, 2003.Google Scholar
  34. 34.
    Becke, A.D., J. Chem. Phys., 1993, vol. 98, no. 7, p. 5648.CrossRefGoogle Scholar
  35. 35.
    Lee, C. T., Yang, W. T., and Parr, R. G., Phys. Rev., 1988, vol. 37, no. 2, p. 785.CrossRefGoogle Scholar
  36. 36.
    Hariharan, P.C. and Pople, J.A., Theor. Chim. Acta, 1973, vol. 28, no. 3, p. 213.CrossRefGoogle Scholar
  37. 37.
    Bader, R. W., Atoms in Molecules: A Quantum Theory, Oxford: Clarendon, 1990.Google Scholar
  38. 38.
    Popelier, P.L.A., Atoms In Molecules. An Introduction, Harlow: Prentice Hall, 2000.Google Scholar
  39. 39.
    Biegler-König, F.W., Bader, R.F.W., and Tang, T. H., J. Comput. Chem., 1982, vol. 3, no. 3, p. 317.CrossRefGoogle Scholar
  40. 40.
    Popelier, P.L.A and Bone, R.G.A., MORPHY98, A Topological Analysis Program, UMIST (England, EU), 1999.Google Scholar
  41. 41.
    Boronat, M., Orti, E., Viruela, P. M., and Tomas, F., J. Mol. Struct. (Theochem), 1997, vol. 390, p. 149.CrossRefGoogle Scholar
  42. 42.
    Ghosh, A. and Almlof, J., J. Phys. Chem., 1995, vol. 99, no. 4, p. 1073.CrossRefGoogle Scholar
  43. 43.
    NIST-Chemistry-Webbook, http://webbook.nist.gov/chemistry/vol. June-2005
  44. 44.
    Minkin, V.I. and Minyaev, R.M., Chem. Rev., 2001, vol. 101, no. 5, p. 1247.CrossRefGoogle Scholar
  45. 45.
    Sanz, P., Yanez, M., and Mo, O., Chem. Eur. J., 2003, vol. 9, no. 18, p. 4548.CrossRefGoogle Scholar
  46. 46.
    Picazo, O., Alkorta, I., and Elguero, J., J. Org. Chem., 2003, vol. 68, no. 19, p. 7485.CrossRefGoogle Scholar
  47. 47.
    Espinosa, E., Alkorta, I., Elguero, J., and Molins, E., J. Chem. Phys., 2002, vol. 117, no. 12, p. 5529.CrossRefGoogle Scholar

Copyright information

© MAIK Nauka 2008

Authors and Affiliations

  1. 1.Instituto de Química MédicaCSICMadridSpain

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