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Aromaticity of corazulenic fullerenes

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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.

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References

  1. E.C. Kirby, in From Chemical Topology to Three-Dimensional Geometry, ed. by A.T. Balaban (Plenum Press, New York, 1997), pp. 263–296

  2. Bühl M., Hirsch A.: Chem. Rev. 101, 1153–1183 (2001)

    Article  Google Scholar 

  3. Randić M.: Chem. Rev. 103, 3449–3605 (2003)

    Article  Google Scholar 

  4. Salem K.: MATCH, Commun. Math. Comput. Chem. 53, 419–426 (2005)

    CAS  Google Scholar 

  5. Salem K.: MATCH, Commun. Math. Comput. Chem. 53, 427–440 (2005)

    CAS  Google Scholar 

  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. 1–8

  7. Cyvin S.J., Cyvin B.N., Brunvoll J.: MATCH, Commun. Math. Comput. Chem. 25, 105–113 (1990)

    CAS  Google Scholar 

  8. Dias J.R.: J. Chem. Inf. Model. 45, 562–571 (2005)

    Article  CAS  Google Scholar 

  9. Vukičević D., Kroto H.W., Randić M.: Croat. Chem. Acta 78, 223–234 (2005)

    Google Scholar 

  10. Clar E.: Polycyclic Hydrocarbons. Academic Press, London (1964)

    Google Scholar 

  11. Clar E.: The Aromatic Sextet. Wiley, New York (1972)

    Google Scholar 

  12. Fries K., Liebigs J.: Ann. Chem. 454, 121–324 (1927)

    CAS  Google Scholar 

  13. Shiu W.-Ch., Lam P.Ch.B., Zhang H.: Theochem 4, 0210 (2000)

    Google Scholar 

  14. Fowler P.W., Pisanski T.: J. Chem. Soc. Faraday Trans. 90, 2865–2871 (1994)

    Article  CAS  Google Scholar 

  15. Dias J.R.: J. Chem. Inf. Comput. Sci. 39, 144–150 (1999)

    CAS  Google Scholar 

  16. S.J. Cyvin, I. Gutman, Kekule Structures in Benzenoid Hydrocarbons. Lecture Notes in Chemistry, vol. 46 (Springer-Verlag, Berlin, 1988)

  17. Dias J.R.: Thermochim. Acta 122, 313–337 (1987)

    Article  CAS  Google Scholar 

  18. Dias J.R.: J. Chem. Inf. Comput. Sci. 31, 89–96 (1991)

    CAS  Google Scholar 

  19. Kirby E.C.: Fullerene Sci. Technol. 2, 395–404 (1994)

    CAS  Google Scholar 

  20. Kirby E.C.: MATCH, Commun. Math. Comput. Chem. 33, 147–156 (1996)

    CAS  Google Scholar 

  21. E.C. Kirby, in Nanostructures-Novel Architecture, ed. by M.V. Diudea (NOVA, New York, 2005), pp. 175–191

  22. Nikolić S., Trinajstić N.: Gazz. Chim. Ital. 120, 685–689 (1990)

    Google Scholar 

  23. Gutman I., Cyvin S.: MATCH, Commun. Math. Comput. Chem. 30, 93–102 (1994)

    CAS  Google Scholar 

  24. Gutman I., Cyvin S.J., Petrovic V., Teodorovic A.: Polycyclic Aromat. Compds. 4, 183–189 (1994)

    Article  CAS  Google Scholar 

  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. 297–341

  26. Eberhard V.: Zur Morphologie der Polyeder. Teubner, Leipzig (1891)

    Google Scholar 

  27. Fowler P.W.: Chem. Phys. Lett. 131, 444–450 (1986)

    Article  CAS  Google Scholar 

  28. Diudea M.V.: Phys. Chem. Chem. Phys. 7, 3626–3633 (2005)

    Article  CAS  Google Scholar 

  29. Diudea M.V.: Forma (Tokyo) 19, 131–163 (2004)

    Google Scholar 

  30. M.V. Diudea, in Nanostructures-Novel Architecture, ed. by M.V. Diudea (NOVA, New York, 2005), pp. 203–242

  31. M.V. Diudea, in Nanostructures-Novel Architecture, ed. by M.V. Diudea (NOVA, New York, 2005), pp. 111–126

  32. M. Stefu, M.V. Diudea, CageVersatile 1.3 (“Babes-Bolyai” University, Cluj, 2003)

  33. Hosoya H., Tsukano Y., Nakada K., Iwata S., Nagashima U.: Croat. Chem. Acta 77, 89–95 (2004)

    CAS  Google Scholar 

  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. 155–158

  35. Clar E., Sanigok U., Zander M.: Tetrahedron 24, 2817–2823 (1968)

    Article  CAS  Google Scholar 

  36. Schulman J.M., Disch R.L.: J. Phys. Chem. A 101, 9176–9179 (1997)

    Article  CAS  Google Scholar 

  37. Keith T.A., Bader R.F.W.: Chem. Phys. Lett. 210, 223–231 (1993)

    Article  CAS  Google Scholar 

  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. 1–88

  39. Acocella A., Havenith E.W.A., Steiner E., Fowler P.W., Jenneskens L.W.: Chem. Phys. Lett. 363, 64–72 (2002)

    Article  CAS  Google Scholar 

  40. Julg A., Francois Ph.: Theor. Chim. Acta 7, 249–261 (1967)

    Article  Google Scholar 

  41. A. Julg, in Aromaticity, Pseudoaromaticity, Anti-Aromaticity, ed. by E.D. Bergmann, B. Pullman (Israel Acad. Sci. Human., Jerusalem, 1971), p. 383

  42. Bird C.W.: Tetrahedron 41, 1409–1414 (1985)

    Article  CAS  Google Scholar 

  43. Krygowski T.M.: J. Chem. Inf. Comput. Sci. 33, 70–78 (1993)

    CAS  Google Scholar 

  44. Krygowski T.M., Ciesielski A.: J. Chem. Inf. Comput. Sci. 35, 203–210 (1995)

    CAS  Google Scholar 

  45. Krygowski T.M., Ciesielski A.: J. Chem. Inf. Comput. Sci. 35, 1001–1003 (1995)

    CAS  Google Scholar 

  46. Dewar M.J.S.: Angew. Chem. Int. Ed. Engl. 10, 761–870 (1971)

    Article  CAS  Google Scholar 

  47. Jug K., Koester A.M.: J. Phys. Org. Chem. 4, 163–169 (1991)

    Article  CAS  Google Scholar 

  48. Balaban A.T., Oniciu D.C., Katritzky A.R.: Chem. Rev. 104, 2777–2812 (2004)

    Article  CAS  Google Scholar 

  49. Fowler P.W., Collins D.J., Austin S.J.: J. Chem. Soc. Perkin Trans. 2, 275–277 (1993)

    Google Scholar 

  50. Stone A.J., Wales D.J.: Chem. Phys. Lett. 128, 501–503 (1986)

    Article  CAS  Google Scholar 

  51. Diudea M.V., Ştefu M., John P.E., Graovac A.: Croat. Chem. Acta 79, 355–362 (2006)

    CAS  Google Scholar 

  52. Cs.L. Nagy, M.V. Diudea, JSCHEM Software (“Babes-Bolyai” University, Cluj, 2006)

  53. Sakurai H., Daiko T., Hirao T.: Science 301, 1878 (2003)

    Article  CAS  Google Scholar 

  54. Sakurai H., Daiko T., Sakane H., Amaya T., Hirao T.: J. Am. Chem. Soc. 127, 11580–11581 (2005)

    Article  CAS  Google Scholar 

  55. M.V. Diudea, Cs.L. Nagy, Periodic Nanostructures, Chap. 6 (Springer, 2007)

  56. Diudea M.V., Vukičević D., Nanosci J.: Nanotechnol. 7, 1321–1328 (2006)

    Google Scholar 

  57. Vukičević D., Randić M.: Chem. Phys. Lett. 401, 446–450 (2005)

    Article  Google Scholar 

  58. Ciesielski A., Cyranski M.K., Krygowski T.M., Fowler P.W., Lillington M.: J. Org. Chem. 71, 6840–6845 (2006)

    Article  CAS  Google Scholar 

  59. Endo M., Kroto H.W.: J. Phys. Chem. 96, 6941–6944 (1992)

    Article  CAS  Google Scholar 

  60. Diudea M.V.: Phys. Chem. Chem. Phys. 4, 4740–4746 (2002)

    Article  CAS  Google Scholar 

  61. S. Chigher, M.V. Diudea, Kekule Structure Counter 1.1 (“Babes-Bolyai” University, Cluj, 2006)

  62. Haddon R.C.: J. Am. Chem. Soc. 109, 1676–1685 (1987)

    Article  CAS  Google Scholar 

  63. Haddon R.C.: J. Am. Chem. Soc. 112, 3385–3389 (1990)

    Article  CAS  Google Scholar 

  64. Haddon R.C.: J. Am. Chem. Soc. 119, 1797–1798 (1997)

    Article  CAS  Google Scholar 

  65. Haddon R.C.: J. Am. Chem. Soc. 120, 10494–10496 (1998)

    Article  CAS  Google Scholar 

Download references

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Authors and Affiliations

  1. Faculty of Chemistry and Chemical Engineering, Babes-Bolyai University, 400028, Cluj, Romania

    Mircea V. Diudea & Aniela E. Vizitiu

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  1. Mircea V. Diudea
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  2. Aniela E. Vizitiu
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Correspondence to Mircea V. Diudea.

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Diudea, M.V., Vizitiu, A.E. Aromaticity of corazulenic fullerenes. J Math Chem 45, 330–353 (2009). https://doi.org/10.1007/s10910-008-9409-0

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