Journal of Structural Chemistry

, Volume 49, Issue 6, pp 979–985 | Cite as

Aromatic stability energy studies on five-membered heterocyclic C4H4M (M = O, S, Se, Te, NH, PH, AsH and SbH): DFT calculations

  • E. VessallyEmail author


Energetic, geometric and magnetic criteria were applied to examine the stability and/or aromatic character for the cyclic molecules C 4 H 4 M (M = O, S, Se, Te, NH, PH, AsH and SbH) at B3LYP/6-311++G** and MP2/6-311++G** levels of theory. The isodesmic reactions and nuclear independent chemical shifts (NICS) calculations were utilized to examine the molecules for energetic and magnetic criteria, respectively. The isodesmic reaction energies reveal that thiophene (C 4 H 4 S, −23.269 kcal/mol) and pyrrole (C 4 H 4 NH, −20.804 kcal/mol) have the greatest aromatic stabilization energies and tellurophene (C 4 H 4 Te, −15.114 kcal/mol) and stibole (C 4 H 4 SbH, −1.169 kcal/mol) have the lowest aromatic stabilization energies in their corresponding groups at MP2/6-311++G**. The NICS calculations confirmed the results obtained through isodesmic reaction energies.


aromatic character isodesmic reaction NICS five-membered heterocycle C4H4


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    V. I. Minkin, M. N. Glukhovtsev, and B. Ya. Simkin, Aromaticity and Antiaromaticity — Electronic and Structural Aspects, Wiley, New York (1994).Google Scholar
  2. 2.
    T. M. Krygowski, M. K. Cyranski, Z. Czarnocki, et al., Tetrahedron, 56, 1783–1796 (2000).CrossRefGoogle Scholar
  3. 3.
    F. Sondheimer, Pure Appl. Chem., 7, 363–388 (1963).CrossRefGoogle Scholar
  4. 4.
    M. J. S. Dewar, Tetrahedron, 22(Supplement 8), 75–102 (1966).CrossRefGoogle Scholar
  5. 5.
    J. A. Elvidge and L. M. Jackman, J. Chem. Soc., 859–866 (1961).Google Scholar
  6. 6.
    M. K. Cyranski, T. M. Krygowski, A. R. Katritzky, and P. V. R. Schleyer, J. Org. Chem., 67, 1333–1338 (2002).CrossRefGoogle Scholar
  7. 7.
    J. Karolak-Wojciechowska, A. Mrozek, R. Czylkowski, et al., J. Mol. Struct., 839, 125–131 (2007).CrossRefGoogle Scholar
  8. 8.
    C. Domene, L. W. Jenneskens, and P. W. Fowler, Tetrahedron Lett., 46, 4077–4080 (2005).CrossRefGoogle Scholar
  9. 9.
    J. Van Droogenbroeck, C. Van Alsenoy, and F. Blockhuys, J. Phys. Chem. A, 109, 4847–4851 (2005).CrossRefGoogle Scholar
  10. 10.
    W. J. Hehre, R. Ditchfield, L. Radom, and J. A. Pople, J. Am. Chem. Soc., 92, 4796–4801 (1970).CrossRefGoogle Scholar
  11. 11.
    P. George, M. Trachtman, C. W. Bock, and A. M. Brett, J. Chem. Soc., Perkin Trans. II, 1222–1227 (1976).Google Scholar
  12. 12.
    W. J. Hehre, L. Radom, P. V. R. Schleyer, and J. A. Pople, Ab Initio Molecular Orbital Theory, Wiley, New York (1986).Google Scholar
  13. 13.
    P. V. R. Schleyer, C. Maerker, A. Dransfield, et al., J. Am. Chem. Soc., 118, 6317/6318 (1996).Google Scholar
  14. 14.
    a) M. K. Cyranski, P. v. R. Schleyer, T. M. Krygowski, et al., Tetrahedron, 59, 1657–1665 (2003)CrossRefGoogle Scholar
  15. 14.
    b) A. Stanger, J. Org. Chem., 71, 883–893 (2006)CrossRefGoogle Scholar
  16. 14.
    c) Z. Chen, C. S. Wannere, C. Corminboeuf, et al., Chem. Rev., 105, 3842–3888 (2005).CrossRefGoogle Scholar
  17. 15.
    a) M. Z. Kassaee, S. Arshadi, M. Acedy, and E. Vessally, J. Organomet. Chem., 690, 3427–3439 (2005)CrossRefGoogle Scholar
  18. 15.
    b) E. Vessally, N. Chalyavi, A. Rezaei, and M. Nikoorazm, Russ. J. Phys. Chem., 81, 1820–1824 (2007)CrossRefGoogle Scholar
  19. 15.
    c) E. Vessally, A. Rezaei, N. Chalyavi, and M. Nikoorazm, J. Chin. Chem. Soc., 54, 1583–1589 (2007)Google Scholar
  20. 15.
    d) E. Vessally, Heteroatom. Chem., 19, 245–251 (2008)CrossRefGoogle Scholar
  21. 15.
    e) E. Vessally et. al., Chin. J. Inorg. Chem., 24, 631 (2008).Google Scholar
  22. 16.
    C. Lee, W. Yang, and R. G. Parr, Phys. Rev., 37B, 785–789 (1988).Google Scholar
  23. 17.
    A. D. Becke, J. Chem. Phys., 98, 5648–5652 (1993).CrossRefGoogle Scholar
  24. 18.
    M. J. Frisch, M. Head-Gordon, and J. A. Pople, Chem. Phys. Lett., 166, 281–289 (1990).CrossRefGoogle Scholar
  25. 19.
    M. J. Frisch, G. W. Trucks, G. E. Schlegel, et. al., Gaussian-98, Revision A.6, Gaussian Inc., Pittsburgh PA (1998).Google Scholar
  26. 20.
    H. B. Schlegel and M. J. Frisch, Int. J. Quantum Chem., 54, 83–87 (1995).CrossRefGoogle Scholar
  27. 21.
    D. E. Manolopoulos, J. C. May, and S. E. Down, Chem. Phys. Lett., 181, 105–111 (1991).CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2008

Authors and Affiliations

  1. 1.Payame Noor UnivesityZanjanIran

Personalised recommendations