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Pairwise energy effect of cyclic conjugation in benzo-annelated perylenes

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Abstract

Previous analysis of cyclic conjugation in benzo-annelated perylenes has revealed that annelation of a benzene ring in the angular position increases the extent of cyclic conjugation in the central ring whereas annelation of a benzene ring in the linear position reduces it. We now present a general method for assessing the effect of a ring on the energy effect of cyclic conjugation in another ring. The respective quantity, referred to as the pairwise energy effect, is used to rationalize specific modes of cyclic conjugation in benzo-annelated perylenes.

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References

  1. Randić M (2003) Chem Rev 103:3449

    Article  Google Scholar 

  2. Balaban AT, PvR Schleyer, Rzepa HS (2005) Chem Rev 105:3436

    Article  CAS  Google Scholar 

  3. Gutman I, Cyvin SJ (1989) Introduction to the theory of benzenoid hydrocarbons. Springer, Berlin

    Google Scholar 

  4. Đurđević J, Gutman I, Terzić J, Balaban AT (2009) Polycyclic Arom Comp 29:90

    Article  Google Scholar 

  5. Gutman I, Đurđević J (2009) J Serb Chem Soc 74:765

    Article  CAS  Google Scholar 

  6. Đurđević J, Radenković S, Gutman I, Marković S (2009) Monatsh Chem 140:1305

    Article  Google Scholar 

  7. Radenković S, Đurđević J, Gutman I (2009) Chem Phys Lett 475:289

    Article  Google Scholar 

  8. Gutman I, Turković N, Jovičić J (2004) Monatsh Chem 135:1389

    Article  CAS  Google Scholar 

  9. Radenković S, Linert W, Gutman I, Jeremić S (2009) Indian J Chem 48A:1657

    Google Scholar 

  10. Gutman I (2010) J Math Chem. doi:10.1007/s10910-009-9655-9

  11. Aihara J (1977) J Am Chem Soc 99:2048

    Article  CAS  Google Scholar 

  12. Bosanac S, Gutman I (1977) Tetrahedron 33:1809

    Article  Google Scholar 

  13. Bosanac S, Gutman I (1977) Z Naturforsch A 32:10

    Google Scholar 

  14. Herndon WC (1982) J Am Chem Soc 104:3541

    Article  CAS  Google Scholar 

  15. Gutman I (2005) Monatsh Chem 136:1055

    Article  CAS  Google Scholar 

  16. Graovac A, Gutman I, Trinajstić N, Živković T (1972) Theor Chim Acta 26:67

    Article  CAS  Google Scholar 

  17. Aihara J (1976) J Am Chem Soc 98:6840

    Article  CAS  Google Scholar 

  18. Gutman I (1994) J Math Chem 16:73

    Article  CAS  Google Scholar 

  19. Coulson CA, Jacobs J (1949) J Am Chem Soc 2805

Download references

Acknowledgments

S.R. and I.G. were supported by the Serbian Ministry of Science, through Grant no. 144015G. W.L. was supported by the Austrian Science Fund (FWF) (Project 19335-N17).

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Correspondence to Slavko Radenković.

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Gutman, I., Radenković, S. & Linert, W. Pairwise energy effect of cyclic conjugation in benzo-annelated perylenes. Monatsh Chem 141, 401–407 (2010). https://doi.org/10.1007/s00706-010-0270-z

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  • DOI: https://doi.org/10.1007/s00706-010-0270-z

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