Benzenoid hydrocarbon aromaticity in terms of charge density descriptors

Canadian Journal of Chemistry

Volumn 75, Issue 9, 1997, Pages 1174-1181

  Howard, S T ^a   Krygowski, T M ^b  

^a CARDIFF UNIVERSITY   (United Kingdom)

^b UNIVERSITY OF WARSAW   (Poland)

Author keywords

Aromaticity; Aromaticity index; Electron density; HOMA; NICS; Quantum chemistry

Indexed keywords

BENZENE; CARRIER CONCENTRATION; CHEMICAL BONDS; NAPHTHALENE; QUANTUM THEORY;

ANTHRACENE; AROMATICITY INDEX; CHARGE DENSITY; CHRYSENE; CORONENE; PERYLENE; PHENANTHRENE; PYRENE; TETRACENE; TRIPHENYLENE;

AROMATIC HYDROCARBONS;

EID: 0031224490     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v97-141     Document Type: Article

References (42)

1. A. Kekule. Bull. Soc. Chim. Fr. 3, 98 (1865).
2. E. Erlenmayer. Ann. Chem. Pharm. 137, 327 (1866).
3. (a) E. Hückel. Z. Phys. 70, 204 (1931);
4. (b) Grundzüge der Theorie Ungesättiger und Aromatischer Verbindungen Chemie. Berlin. 1938.
5. L.M. Jackman and J.A. Elvidge. J. Chem. Soc. 859 (1961).
6. F. Sondheimer. Pure Appl. Chem., 7, 363 (1964).
7. G. Wheland. Resonance in organic chemistry. Wiley, New York. 1955.
8. A. Streitwieser, Jr. Molecular orbital theory for organic chemists. Wiley, New York. 1961.
9. M.J.S. Dewar and C. de Llano. J. Am. Chem. Soc. 91, 789 (1969).
10. B.A. Hess, Jr. and L.J. Schaad. J. Am. Chem. Soc. 93, 305 (1971).
11. B.A. Hess, Jr., L.J. Schaad, and C.W. Holyoke. Tetrahedron, 28, 3657 (1972).
12. M. Randić. Chem. Phys. Lett. 38, 68 (1976).
13. I. Gutman and S.J. Cyvin. Introduction to the theory of benzenoid hydrocarbons. Springer Verlag, Berlin. 1989.
14. D.J. Klein. Pure Appl. Chem. 61, 2107 (1989).
15. A. Julg and P.H. Francois. Theor. Chim. Acta, 7, 249 (1967).
16. J. Kruszewski and T.M. Krygowski. Tetrahedron Lett. 3842 (1972).
17. T.M. Krygowski. J. Chem. Inf. Comput. Sci. 33, 70 (1993).
18. C.W. Bird. Tetrahedron, 41, 1409 (1985).
19. C.W. Bird. Tetrahedron, 42, 89 (1986).
20. G. Binsch and I. Tamir. J. Am. Chem. Soc. 91, 450 (1969).
21. A. Ciesielski, T.M. Krygowski, C.W. Bird, and A. Kotschy. J. Chem. Inf. Comput. Sci. 35, 203 (1995).
22. A.F. Pohzarsky. Chem. Heterocycl. Comp. 21, 717 (1985).
23. M.H. Palmer, R.H. Findley, and W.J. Moyes. J. Chem. Soc. Perkin Trans. 2, 841 (1975).
24. P. von R. Schleyer, P.K. Freeman, H. Jiao, and B. Goldfuss. Angew. Chem. Int. Ed. Engl. 34, 337 (1995).
25. R.F.W. Bader and T.A. Keith. J. Chem. Phys. 99, 3683 (1993).
26. C.P. Slichter. Principles of magnetic resonance. 2nd ed. Springer Verlag, Berlin. 1978. pp. 71-76.
27. K. Jug and A. Koester. J. Phys. Org. Chem. 4, 163 (1991).
28. Z.X. Zhou, R.G. Parr, and J.F. Garst. Tetrahedron Lett. 29, 4843 (1988).
29. Z.X. Zhou and R.G. Parr. J. Am. Chem. Soc. 111, 7371 (1989).
30. A.R. Katritzky, P. Barczynski, G. Musumurra, D. Pisano, and M. Szafran. J. Am. Chem. Soc. 111, 7 (1989).
31. R.F.W. Bader. Atoms in molecules: a quantum theory. Oxford University Press, Oxford. 1990.
32. R.J. Boyd and K.E. Edgecombe. J. Comput. Chem. 8, 489 (1987).
33. R.J. Boyd and K.E. Edgecombe. J. Am. Chem. Soc. 110, 4182 (1988).
34. V.I. Minkin, M.N. Glukhovtsev, and B.Y. Simkin. Aromaticity and antiaromaticity, electronic and structural aspects. John Wiley & Sons, New York. 1994. pp. 84-87.
35. S.S. Shaik, P.C. Hiberty, J.M. Lefour, and G. Ohanessian. J. Am. Chem. Soc. 109, 363 (1987).
36. K. Jug and A. Koester. J. Am. Chem. Soc. 112, 6772 (1990).
37. E.D. Glendening, R. Faust, A. Streitwieser, K.P.C. Vollhardt, and F. Weinhold. J. Am. Chem. Soc. 115, 10952 (1993).
38. I. Gutman, S. Markovic, and G.G. Hall. Chem. Phys. Lett. 234, 21 (1995).
39. M.W. Schmidt, K.K. Baldridge, J.A. Boatz, S.T. Elbert, M.S. Gordon, J.H. Jensen, S. Koseki, N. Matsunaga, K.A. Nguyen, S.J. Su, T.L. Windus, M. Dupuis, and J.A. Montgomery. J. Comput. Chem. 14, 1347 (1993).
40. F.W. Biegler-Konig, R.F.W. Bader, and T.H. Tang. J. Comput. Chem. 13, 317 (1992).
41. P.C. Hariharan and J.A. Pople. Theor. Chim. Acta, 28, 213 (1973).
42. P. von R. Schleyer, C. Maerker, A. Dransfeld, H. Jaio, and N.J.R.V. Hommes. J. Am. Chem. Soc. 118, 6317 (1996).