Effect of benzocyclobutadieno-annelation on cyclic conjugation in perylene
DOI:
https://doi.org/10.20450/mjcce.2011.38Keywords:
polycyclic aromatic hydrocarbons, cyclic conjugation, energy effect of cyclic conjugation, perylene, benzocyclobutadieno-annelated peryleneAbstract
Earlier studies showed that the intensity of cyclic conjugation in the central ring R of perylenecan be significantly altered by means of benzo-annelation. In particular, linear (resp. angular) benzoannelation
was found to decrease (resp. increase) the intensity of cyclic conjugation in R .We now examine
the analogous effect of benzocyclobutadieno-annelation, and show that linear annelation strongly increases
the cyclic conjugation in R, whereas the effect of angular annelation is negligibly small.
References
I. Gutman, N. Turković, J. Jovičić, Cyclic conjugation in benzo-annelated perylenes: How empty is the “empty” ring? Monatsh. Chem. 135 1389–1394 (2004).
S. Jeremić, S. Radenković, I. Gutman, Cyclic conjugation in benzo-annelated coronenes. Maced. J. Chem. Chem. Engin. 29 63–69 (2010).
S. Jeremić, S. Radenković, I. Gutman, Cyclic conjugation in benzo-annelated triphenylenes, J. Serb. Chem. Soc. 75 943–950 (2010).
T. Balaban, J. Đurđević, I. Gutman, S. Jeremić, S. Radenković, Correlations between local aromaticity indices of bipartite conjugated hydrocarbons, J. Phys. Chem. A 114 5870–5877 (2010).
T. Balaban, I. Gutman, S. Jeremić, J. Đurđević, Effect of benzo-annelation on cyclic conjugation, Monatsh. Chem. 142 53–57 (2011).
E. Clar, The Aromatic Sextet, Wiley, London, 1972.
I. Gutman, S. J. Cyvin, Introduction to the Theory of Benzenoid Hydrocarbons, Springer-Verlag, Berlin, 1989.
M. Randić, Aromaticity of polycyclic conjugated hydrocarbons. Chem. Rev. 103 3449–3606 (2003).
T. Balaban, M. Randić, in: M. V. Putz (Ed.), Advances in Physics and Chemistry of Carbon Bonding and Structures, Springer-Verlag, Berlin, 2011, in press.
Gutman, B. Furtula, A. T. Balaban, Effect of benzocyclobutadieno-annelation on cyclic conjugation in fluoranthene congeners, J. Serb. Chem. Soc. 76, 733–741 (2011).
I. Gutman, Cyclic conjugation energy effects in polycyclic π-electron systems. Monatsh. Chem. 136, 1055–1069 (2005).
I. Gutman, Mathematical modeling of chemical phenomena. in: A. Graovac, I. Gutman, D. Vukičević (Eds.), Mathematical Methods and Modelling for Students of Chemistry and Biology,Hum, Zagreb, 2009, pp. 13–27.
I. Gutman, V. Ivanov-Petrović, Unusual modes of cyclic conjugation in phenylenes. Bull. Chem. Technol. Maced. 16, 91–96 (1997).
I. Gutman, Ž. Tomović, On cyclic conjugation of the members of the pyrene/peropyrene series and their formally π-localized derivatives. Bull. Chem.Technol. Maced. 20, 33–37 (2001).
I. Gutman, S. Stanković, Why is phenanthrene more stable than anthracene?, Maced. J. Chem.Chem. Eng. 26, 111–114 (2007).
I. Gutman, On a class of integrals encountered in theoretical chemistry, Int. J. Chem. Model. 2, 335–341 (2010).
Suggested by the anonymous referee.
Downloads
Published
How to Cite
Issue
Section
License
The authors agree to the following licence: Attribution-NonCommercial 4.0 International (CC BY-NC 4.0)
- Share — copy and redistribute the material in any medium or format
- Adapt — remix, transform, and build upon the material
- for any purpose, even commercially.
Under the following terms:
Attribution — You must give appropriate credit, provide a link to the license, and indicate if changes were made. You may do so in any reasonable manner, but not in any way that suggests the licensor endorses you or your use.
- NonCommercial — You may not use the material for commercial purposes.