How to find the fries structures for benzenoid hydrocarbons

Symmetry

Volumn 2, Issue 3, 2010, Pages 1390-1400

  Ciesielski, Arkadiusz ^a,b   Krygowski, Tadeusz M ^b   Cyrański, Michał K ^b  

^a INSTITUTE OF BIOCHEMISTRY AND BIOPHYSICS   (Poland)

^b UNIVERSITY OF WARSAW   (Poland)

Author keywords

Aromaticity; Benzenoid hydrocarbons; Fries structure; Graph topology

Indexed keywords

EID: 84555199250     PISSN: None     EISSN: 20738994     Source Type: Journal    
DOI: 10.3390/sym2031390     Document Type: Article

References (32)

1. Garratt, P.J. Aromaticity; Wiley Inc.: New York, NY, USA, 1986.
2. Lloyd, D. The Chemistry of Conjugated Cyclic Compounds: To Be or Not to Be like Benzene; J. Wiley: New York, NY, USA, 1990.
3. Minkin, V.I.; Glukhovtsev, M.N.; Simkin, B.Y. Aromaticity and Antiaromaticity; J. Wiley: New York, NY, USA, 1994.
4. Hopf, H. Classics in Hydrocarbon Chemistry: Syntheses, Concepts, Perspectives; Wiley, VCH: Weinheim, Germany, 2000.
5. Pascal, R.A., Jr. Twisted Acenes. Chem. Rev. 2006, 106, 4809-4819.
6. Schleyer, P.v.R. Special Issue of the Journal Devoted to Aromaticity. Chem. Rev. 2001, 101, 1115-1566.
7. Lazzeretti, P.; Corminboeuf, C.; Heine, T.; Seifert, G.; Schleyer, P.v.R.; Weber, J.; De Proft, F.; Geerlings, P.; Hiberty, P.C.; Shaik, S.; Rassat, A.; Soncini, A.; Fowler, P.W.; Jenneskens, L.W.; Havenith, R.W.A; Engelberts, J.J.; Fowler, P.W.; Steiner, E.; van Lenthe, J.; Poater, J.; Garcia-Cruz. I.; Illas, F.; Solà, M.; Diudea, M.V.; Taylor, R.; Steiner E, Fowler, P.W.; Steiner, E.; Shetty, S.; Kanhere, D.; Pal, S.; Krygowski, T.M.; Cyrański, M.K. Lectures at the European Science Foundation Workshop: New Perspectives on Aromaticity, Exeter, UK, 5-9 July, 2003. Phys. Chem. Chem. Phys. 2005, 6, 217-339.
8. Schleyer, P.v.R. Special Issue of the Journal Devoted to Delocalization Sigma and Pi. Chem. Rev. 2005, 105, 3433-3948.
9. Randić, M. Aromaticity of Polycyclic Conjugated Hydrocarbons. Chem. Rev. 2003, 103, 3449-3605.
10. Clar, E. Polycyclic Hydrocarbons; Academic Press: London, UK, 1964; Volume 1-2.
11. Clar, E. The aromatic Sextet; Wiley: New York, NY, USA, 1972.
12. Poater, J.; Solà, M.; Duran, M.; Fradera, X. The Calculation of Electron Localization and Delocalization Indices at the Hartree-Fock, Density Functional and Post-Hartree-Fock Levels of Theory. Theor. Chem. Acc. 2002, 107, 362-371.
13. Poater, J.; Fradera, X; Duran, M. Solà, M. The Delocalization Index as an Electronic Aromaticity Criterion: Application to a Series of Planar Polycyclic Aromatic Hydrocarbons. Chem. Eur. J. 2003, 9, 400-406.
14. Portella, G.; Poater J., Solà; M. Assessment of Clar's Aromatic π-Sextet Rule by Means of PDI, NICS and HOMA Indicators of Local Aromaticity. J. Phys. Org. Chem. 2005, 18, 785-791.
15. Faglioni, F.; Ligabue, A.; Pelloni, S.; Soncini A.; Viglione R.G.; Ferraro M.B., Zanasi R., Lazzaretti P. Why Downfield Proton Chemical Shifts Are Not Reliable Aromaticity Indicators? Org. Lett. 2005, 7, 3457-3460.
16. Maksić, Z.B.; Barić, D.; Muller, T. Clar's Sextet Rule Is a Consequence of the σ-Electron Framework. J. Phys. Chem. 2006, 110, 10135-10147.
17. Bultinck, P.; Ponec, R.; Gallegos, A; Fias, S.; Van Damme, S.; Carbó-Dorca, R. Generalized Polansky Index as an Aromaticity Measure in Polycyclic Aromatic Hydrocarbons. Croat. Chem. Acta 2006, 79, 363-371.
18. Bultinck, P. Critical Analysis of the Local Aromaticity Concept in Polyaromatic Hydrocarbons. Farad. Disc. 2007, 135, 347-365.
19. Alonso, M.; Herradon, B. Neural Networks as a Tool to Classify Compounds According to Aromaticity Criteria. Chem. Eur. J. 2007, 13, 3913-3923.
20. Fias, S.; van Damme S.; Bultinck, P. Multidimensionality of Delocalization Indices and Nucleus Independent Chemical Shifts in Polycyclic Aromatic Hydrocarbons. J. Comput. Chem. 2008, 29, 358-366.
21. Fias, S.; Fowler, P.W.; Delgado, J.L.; Hahn U.; Bultinck P. Correlation of Delocalization Indices and Current-Density Maps in Polycyclic Aromatic Hydrocarbons. Chem. Eur. J. 2008, 14, 3093-3099.
22. Balaban, A.T.; Schleyer, P.v.R.; Rzepa, H.S. Crocker, Not Armit and Robinson, Begat the Six Aromatic Electrons. Chem. Rev. 2005, 105, 3436-3447.
23. Balaban, A.T.; Klein, D.J. Claromatic Carbon Nanostructures. J. Phys. Chem. C 2009, 113, 19123-19133.
24. Fries, K. Über bicyclische Verbindungen und ihren Vergleich mit dem Naphtalin. Justus Liebigs Ann. Chem. 1927, 454, 121-324.
25. Graovac, A.; Gutman, I.; Randic, M.; Trinajstic, N. Kekule index for valence bond structures of conjugated polycyclic systems J. Am. Chem. Soc. 1973, 95, 6267-6273.
26. Krygowski, T.M.; Cyrański, M.K. Structural Aspects of Aromaticity. Chem. Rev. 2001, 101, 1385-1419.
27. Schleyer, P.v.R.; Maerker, C.; Dransfeld, A.; Jiao, H.J.; Hommes, N.J.R.V. Nucleus-independent chemical shifts: A simple and efficient aromaticity probe. J. Am. Chem. Soc. 1996, 118, 6317-6318.
28. Chen, Z.; Wannere, C.S.; Corminboeuf, C.; Puchta, R.; Schleyer, P.v.R. Nucleus-Independent Chemical Shifts (NICS) as an Aromaticity Criterion. Chem. Rev. 2005, 105, 3842-3888.
29. Ciesielski, A.; Krygowski, T.M.; Cyrański, M.K.; Dobrowolski, M.A.; Aihara, J.-I. Graphtopological approach to magnetic properties of benzenoid hydrocarbons. Phys. Chem. Chem. Phys. 2009, 11, 11447-11445.
30. Trinajstić, N. Chemical Graph Theory, 2nd ed.; CRC press: Boca Raton, FL, USA, 2000.
31. Horn, R.A., Johnson, C.R. Matrix Analysis; Cambridge University Press: Cambridge, UK, 1985.
32. Horn, R.A., Johnson C.R. Topics in Matrix Analysis; Cambridge University Press: Cambridge, UK, 1994.