Advertisement

Journal of Mathematical Chemistry

, Volume 45, Issue 2, pp 330–353 | Cite as

Aromaticity of corazulenic fullerenes

  • Mircea V. Diudea
  • Aniela E. Vizitiu
Original Paper

Abstract

A novel class of non-classical fullerenes, having pentagon–heptagon pairs, as in azulene, is modeled. The various coverings, sometimes alternating azulenic and benzenic units, are designed by some new sequences of map operations or generalized operations. The hypothetical azulenic fullerenes are characterized by PM3 semiempirical data and POAV1 strain energy SE. Their aromaticity is discussed in the light of several criteria. The HOMA index of aromaticity enabled evaluation of global and local aromaticity of the designed fullerenes.

Keywords

Fullerenes Azulenic fullerenes Tessellation Map operations Aromaticity Local aromaticity 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    E.C. Kirby, in From Chemical Topology to Three-Dimensional Geometry, ed. by A.T. Balaban (Plenum Press, New York, 1997), pp. 263–296Google Scholar
  2. 2.
    Bühl M., Hirsch A.: Chem. Rev. 101, 1153–1183 (2001)CrossRefGoogle Scholar
  3. 3.
    Randić M.: Chem. Rev. 103, 3449–3605 (2003)CrossRefGoogle Scholar
  4. 4.
    Salem K.: MATCH, Commun. Math. Comput. Chem. 53, 419–426 (2005)Google Scholar
  5. 5.
    Salem K.: MATCH, Commun. Math. Comput. Chem. 53, 427–440 (2005)Google Scholar
  6. 6.
    H. Abeledo, G. Atkinson, in Discrete Mathematical Chemistry, ed. by P. Hansen, P.W. Fowler, M. Zheng. DIMACS Series, in Discrete Mathematics and Theoretical Computer Science, vol. 51 (American Mathematical Society, Providence, 2000), pp. 1–8Google Scholar
  7. 7.
    Cyvin S.J., Cyvin B.N., Brunvoll J.: MATCH, Commun. Math. Comput. Chem. 25, 105–113 (1990)Google Scholar
  8. 8.
    Dias J.R.: J. Chem. Inf. Model. 45, 562–571 (2005)CrossRefGoogle Scholar
  9. 9.
    Vukičević D., Kroto H.W., Randić M.: Croat. Chem. Acta 78, 223–234 (2005)Google Scholar
  10. 10.
    Clar E.: Polycyclic Hydrocarbons. Academic Press, London (1964)Google Scholar
  11. 11.
    Clar E.: The Aromatic Sextet. Wiley, New York (1972)Google Scholar
  12. 12.
    Fries K., Liebigs J.: Ann. Chem. 454, 121–324 (1927)Google Scholar
  13. 13.
    Shiu W.-Ch., Lam P.Ch.B., Zhang H.: Theochem 4, 0210 (2000)Google Scholar
  14. 14.
    Fowler P.W., Pisanski T.: J. Chem. Soc. Faraday Trans. 90, 2865–2871 (1994)CrossRefGoogle Scholar
  15. 15.
    Dias J.R.: J. Chem. Inf. Comput. Sci. 39, 144–150 (1999)Google Scholar
  16. 16.
    S.J. Cyvin, I. Gutman, Kekule Structures in Benzenoid Hydrocarbons. Lecture Notes in Chemistry, vol. 46 (Springer-Verlag, Berlin, 1988)Google Scholar
  17. 17.
    Dias J.R.: Thermochim. Acta 122, 313–337 (1987)CrossRefGoogle Scholar
  18. 18.
    Dias J.R.: J. Chem. Inf. Comput. Sci. 31, 89–96 (1991)Google Scholar
  19. 19.
    Kirby E.C.: Fullerene Sci. Technol. 2, 395–404 (1994)Google Scholar
  20. 20.
    Kirby E.C.: MATCH, Commun. Math. Comput. Chem. 33, 147–156 (1996)Google Scholar
  21. 21.
    E.C. Kirby, in Nanostructures-Novel Architecture, ed. by M.V. Diudea (NOVA, New York, 2005), pp. 175–191Google Scholar
  22. 22.
    Nikolić S., Trinajstić N.: Gazz. Chim. Ital. 120, 685–689 (1990)Google Scholar
  23. 23.
    Gutman I., Cyvin S.: MATCH, Commun. Math. Comput. Chem. 30, 93–102 (1994)Google Scholar
  24. 24.
    Gutman I., Cyvin S.J., Petrovic V., Teodorovic A.: Polycyclic Aromat. Compds. 4, 183–189 (1994)CrossRefGoogle Scholar
  25. 25.
    D.J. Klein, H. Zhu, in From Chemical Topology to Three-Dimensional Geometry, ed. by A.T. Balaban (Plenum Press, New York, 1997), pp. 297–341Google Scholar
  26. 26.
    Eberhard V.: Zur Morphologie der Polyeder. Teubner, Leipzig (1891)Google Scholar
  27. 27.
    Fowler P.W.: Chem. Phys. Lett. 131, 444–450 (1986)CrossRefGoogle Scholar
  28. 28.
    Diudea M.V.: Phys. Chem. Chem. Phys. 7, 3626–3633 (2005)CrossRefGoogle Scholar
  29. 29.
    Diudea M.V.: Forma (Tokyo) 19, 131–163 (2004)Google Scholar
  30. 30.
    M.V. Diudea, in Nanostructures-Novel Architecture, ed. by M.V. Diudea (NOVA, New York, 2005), pp. 203–242Google Scholar
  31. 31.
    M.V. Diudea, in Nanostructures-Novel Architecture, ed. by M.V. Diudea (NOVA, New York, 2005), pp. 111–126Google Scholar
  32. 32.
    M. Stefu, M.V. Diudea, CageVersatile 1.3 (“Babes-Bolyai” University, Cluj, 2003)Google Scholar
  33. 33.
    Hosoya H., Tsukano Y., Nakada K., Iwata S., Nagashima U.: Croat. Chem. Acta 77, 89–95 (2004)Google Scholar
  34. 34.
    H. Hosoya, Y. Tsukano, M. Ohuchi, K. Nakada, in Computer Aided Innovation of New Materials II, ed. by M. Doyama, J. Kihara, M. Tanaka, R. Yamamoto (Elsevier, Amsterdam, 1993), pp. 155–158Google Scholar
  35. 35.
    Clar E., Sanigok U., Zander M.: Tetrahedron 24, 2817–2823 (1968)CrossRefGoogle Scholar
  36. 36.
    Schulman J.M., Disch R.L.: J. Phys. Chem. A 101, 9176–9179 (1997)CrossRefGoogle Scholar
  37. 37.
    Keith T.A., Bader R.F.W.: Chem. Phys. Lett. 210, 223–231 (1993)CrossRefGoogle Scholar
  38. 38.
    P. Lazzeretti, in Progress in Nuclear Magnetic Resonance Spectroscopy, vol. 36, ed. by J.W. Emsley, J. Feeney, L.H. Sutcliffe (Elsevier, Amsterdam, 2000), pp. 1–88Google Scholar
  39. 39.
    Acocella A., Havenith E.W.A., Steiner E., Fowler P.W., Jenneskens L.W.: Chem. Phys. Lett. 363, 64–72 (2002)CrossRefGoogle Scholar
  40. 40.
    Julg A., Francois Ph.: Theor. Chim. Acta 7, 249–261 (1967)CrossRefGoogle Scholar
  41. 41.
    A. Julg, in Aromaticity, Pseudoaromaticity, Anti-Aromaticity, ed. by E.D. Bergmann, B. Pullman (Israel Acad. Sci. Human., Jerusalem, 1971), p. 383Google Scholar
  42. 42.
    Bird C.W.: Tetrahedron 41, 1409–1414 (1985)CrossRefGoogle Scholar
  43. 43.
    Krygowski T.M.: J. Chem. Inf. Comput. Sci. 33, 70–78 (1993)Google Scholar
  44. 44.
    Krygowski T.M., Ciesielski A.: J. Chem. Inf. Comput. Sci. 35, 203–210 (1995)Google Scholar
  45. 45.
    Krygowski T.M., Ciesielski A.: J. Chem. Inf. Comput. Sci. 35, 1001–1003 (1995)Google Scholar
  46. 46.
    Dewar M.J.S.: Angew. Chem. Int. Ed. Engl. 10, 761–870 (1971)CrossRefGoogle Scholar
  47. 47.
    Jug K., Koester A.M.: J. Phys. Org. Chem. 4, 163–169 (1991)CrossRefGoogle Scholar
  48. 48.
    Balaban A.T., Oniciu D.C., Katritzky A.R.: Chem. Rev. 104, 2777–2812 (2004)CrossRefGoogle Scholar
  49. 49.
    Fowler P.W., Collins D.J., Austin S.J.: J. Chem. Soc. Perkin Trans. 2, 275–277 (1993)Google Scholar
  50. 50.
    Stone A.J., Wales D.J.: Chem. Phys. Lett. 128, 501–503 (1986)CrossRefGoogle Scholar
  51. 51.
    Diudea M.V., Ştefu M., John P.E., Graovac A.: Croat. Chem. Acta 79, 355–362 (2006)Google Scholar
  52. 52.
    Cs.L. Nagy, M.V. Diudea, JSCHEM Software (“Babes-Bolyai” University, Cluj, 2006)Google Scholar
  53. 53.
    Sakurai H., Daiko T., Hirao T.: Science 301, 1878 (2003)CrossRefGoogle Scholar
  54. 54.
    Sakurai H., Daiko T., Sakane H., Amaya T., Hirao T.: J. Am. Chem. Soc. 127, 11580–11581 (2005)CrossRefGoogle Scholar
  55. 55.
    M.V. Diudea, Cs.L. Nagy, Periodic Nanostructures, Chap. 6 (Springer, 2007)Google Scholar
  56. 56.
    Diudea M.V., Vukičević D., Nanosci J.: Nanotechnol. 7, 1321–1328 (2006)Google Scholar
  57. 57.
    Vukičević D., Randić M.: Chem. Phys. Lett. 401, 446–450 (2005)CrossRefGoogle Scholar
  58. 58.
    Ciesielski A., Cyranski M.K., Krygowski T.M., Fowler P.W., Lillington M.: J. Org. Chem. 71, 6840–6845 (2006)CrossRefGoogle Scholar
  59. 59.
    Endo M., Kroto H.W.: J. Phys. Chem. 96, 6941–6944 (1992)CrossRefGoogle Scholar
  60. 60.
    Diudea M.V.: Phys. Chem. Chem. Phys. 4, 4740–4746 (2002)CrossRefGoogle Scholar
  61. 61.
    S. Chigher, M.V. Diudea, Kekule Structure Counter 1.1 (“Babes-Bolyai” University, Cluj, 2006)Google Scholar
  62. 62.
    Haddon R.C.: J. Am. Chem. Soc. 109, 1676–1685 (1987)CrossRefGoogle Scholar
  63. 63.
    Haddon R.C.: J. Am. Chem. Soc. 112, 3385–3389 (1990)CrossRefGoogle Scholar
  64. 64.
    Haddon R.C.: J. Am. Chem. Soc. 119, 1797–1798 (1997)CrossRefGoogle Scholar
  65. 65.
    Haddon R.C.: J. Am. Chem. Soc. 120, 10494–10496 (1998)CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC 2008

Authors and Affiliations

  1. 1.Faculty of Chemistry and Chemical EngineeringBabes-Bolyai UniversityClujRomania

Personalised recommendations