6-Electron exchange function as a simple estimator of aromaticity in large polyaromatic hydrocarbons

Chemical Physics Letters

Volumn 470, Issue 1-3, 2009, Pages 140-146

  Mandado, Marcos ^a   Mosquera, Ricardo A ^a  

^a UNIVERSITY OF VIGO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; GRAPHITE;

AROMATICITY; BENZENE RINGS; COMPUTATIONAL COSTS; ELECTRON EXCHANGES; ELECTRON-DELOCALIZATION; POLYAROMATIC HYDROCARBONS; RELATIVE VALUES;

HYDROCARBONS;

EID: 63749103666     PISSN: 00092614     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cplett.2009.01.039     Document Type: Article

References (40)

1. Schmitz-Hübsch T., et al. Surf. Sci. 445 (2000) 358
2. Dötz F., Brand J.D., Ito S., Gherghel L., and Müllen K. J. Am. Chem. Soc. 122 (2000) 7707
3. Simpson C.D., Brand J.D., Berresheim A.J., Przybilla L., Räder H.J., and Müllen K. Chem. Eur. J. 8 (2002) 1424
4. Stabel A., Herwig P., Müllen K., and Rabe P. Angew. Chem. Int. Ed. Engl. 34 (1995) 1609
5. Müller M., Kübel Ch., and Müllen K. Chem. Eur. J. 4 (1998) 2099
6. Berresheim A.J., Müller M., and Müllen K. Chem. Rev. 99 (1999) 1747
7. Weisman J.L., Lee T.J., Salama F., and Head-Gordon M. Astrophys. J. 587 (2003) 256
8. Bréchignac P., and Pino T. Astron. Astrophys. 343 (1999) L49
9. Smith G.C., and Sinski J.F. Appl. Spectrosc. 53 (1999) 1459
10. Barone P.M.V.B., Braga R.S., Camilo Jr. A., and Galvão D.S. Theochem 505 (2000) 55
11. Moran D., Stahl F., Bettinger H.F., Schaefer III H.F., and Schleyer P.v.R. J. Am. Chem. Soc. 125 (2003) 6746
12. Hajgató B., and Ohno K. Chem. Phys. Lett. 385 (2004) 512
13. Hajgató B., Deleuze M.S., and Ohno K. Chem. Eur. J. 12 (2006) 5757
14. Steiner E., Fowler P.W., Soncini A., and Jenneskens L.W. Faraday Discuss. 135 (2007) 309
15. Rándic M., and Guo X. New. J. Chem. 23 (1999) 251
16. Rándic M., and Guo X. Int. J. Quant. Chem. 74 (1999) 697
17. Stein S.E., and Brown R.L. Carbon 23 (1985) 105
18. Stein S.E., and Brown R.L. J. Am. Chem. Soc. 109 (1987) 3721
19. Fias S., and Bultinck P. Faraday Discuss. 135 (2007) 381
20. Chen Z., Wannere C.S., Corminboeuf C., Puchta R., and Schleyer P.v.R. Chem. Rev. 105 (2005) 3843 and references therein
21. Fowler P.W., Lillington M., and Olson L.P. Pure Appl. Chem. 79 (2007) 969
22. Kruszewski J., and Krygowski T.M. Tetrahedron Lett. 13 (1972) 3839
23. Heilbronner E., and Bock H. The HMO Model and its Application (1976), Wiley-Interscience, New York
24. Cyránski M.K. Chem. Rev. 105 (2005) 3773 and references therein
25. Randic M. Chem. Rev. 103 (2003) 3449 and references therein
26. Bultinck P., Mandado M., and Mosquera R.A. J. Math. Chem. 43 (2008) 111
27. Fowler P.W., and Steiner E. Chem. Phys. Lett. 364 (2002) 259
28. Mandado M., González-Moa M.J., and Mosquera R.A. J. Comput. Chem. 28 (2007) 127
29. Mandado M., González-Moa M.J., and Mosquera R.A. J. Comput. Chem. 28 (2007) 1625
30. Bultinck P., Ponec R., and Van Damme S. J. Phys. Org. Chem. 18 (2005) 706
31. Bultinck P., Rafat M., Ponec R., Van Gheluwe B., Carbó-Dorca R., and Popelier P. J. Phys. Chem. A 110 (2006) 7642
32. Mulliken R.S. J. Chem. Phys. 23 (1955) 1833
33. Bader R.F.W. Atoms in Molecules - A Quantum Theory. International Series of Monographs on Chemistry No. 22 (1990), Oxford University Press, Oxford
34. Mandado M., Krishtal A., Van Alsenoy C., Bultinck P., and Hermida-Ramón J.M. J. Phys. Chem. A 111 (2007) 11885
35. Bultinck P., Van Alsenoy C., Ayers P.W., and Carbó-Dorca R. J. Chem. Phys. 126 (2007) 144111
36. Expression (1) is fully theoretically founded within the Hartree-Fock, HF, approach. Its extension to density functional methods (using Kohn-Sham, KS, molecular orbitals) or post-HF methods (using natural orbitals) is just an approximation. However, the use of KS molecular orbitals in the calculation of multicenter electron delocalization has been extensively shown to provide a good description of aromaticity.
37. M.J. Frisch et al., Gaussian 03, Revision C.02, Gaussian, Inc., Wallingford CT, 2004.
38. Mandado M., Bultinck P., González-Moa M.J., and Mosquera R.A. Chem. Phys. Lett. 433 (2006) 5
39. Fias S., Van Damme S., and Bultinck P. J. Comput. Chem. 29 (2008) 358
40. Fias S., Fowler P.W., Delgado J.L., Hahn U., and Bultinck P. Chem. Eur. J. 14 (2008) 3093