An ab initio valence bond study on cyclopenta-fused naphthalenes and fluoranthenes

Journal of Organic Chemistry

Volumn 70, Issue 11, 2005, Pages 4484-4489

  Havenith, Remco W A ^a   Van Lenthe, Joop H ^a   Jenneskens, Leonardus W ^b  

^a UTRECHT UNIVERSITY   (Netherlands)

^b UTRECHT UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; ELECTRONS; GROUND STATE; RESONANCE; THERMODYNAMIC STABILITY;

ELECTRON CONJUGATED CIRCUITS; RESONANCE ENERGY; VALENCE BOND (VB);

NAPHTHALENE;

ACENAPHTHYLENE; BENZENE DERIVATIVE; CYCLOPENTA[B,C]ACENAPHTHYLENE; CYCLOPENTA[C,D]FLUORANTHENE; FLUORANTHENE; NAPHTHALENE; NAPHTHALENE DERIVATIVE; PYRACYLENE; UNCLASSIFIED DRUG;

AB INITIO CALCULATION; ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; ELECTRON; ENERGY; ENTHALPY; HYDROGENATION; THERMODYNAMICS;

EID: 19544385779     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050296x     Document Type: Article

References (41)

1. Schleyer, P. v. R.; Jiao, H. Pure Appl. Chem. 1996, 68, 209-218.
2. Lloyd, D. J. Chem. Inf. Comput. Sci. 1996, 36, 442-447.
3. Krygowski, T. M.; Cyrañski, M. K; Czarnocki, Z.; Häfelinger, G.; Katritzky, A. R. Tetrahedron 2000, 56, 1783-1796.
4. Special issue on aromaticity: Chem. Rev. 2001, 101, 1115-1566.
5. Special issue on aromaticity: Phys. Chem. Chem. Phys. 2004, 6, 217-343.
6. Schleyer, P. v. R.; Maerker, C.; Dransfeld, A.; Jiao, H.; van Eikema Hommes, N. J. R. J. Am. Chem. Soc. 1996, 118, 6317-6318.
7. Slayden, S. W.; Liebman, J. F. Chem. Rev. 2001, 101, 1541-1566.
8. Clar, E. The Aromatic Sextet; J. Wiley & Sons: London, 1972.
9. Randić, M. Chem. Phys. Lett. 1976, 38, 68-70.
10. Randić, M. Tetrahedron 1977, 33, 1905-1920.
11. Randić, M. J. Am. Chem. Soc. 1977, 99, 444-450.
12. Randić, M. Chem. Rev. 2003, 103, 3449-3605.
13. Pauling, L.; Wheland, G. W. J. Chem. Phys. 1933, 1, 362-374.
14. Pauling, L. The Nature of the Chemical Bond and the Structure of Molecules and Crystals: An Introduction to Modern Structural Chemistry, 3rd ed.; Cornell University Press: Ithaca, NY, 1960.
15. Havenith, R. W. A.; van Lenthe, J. H.; Dijkstra, F.; Jenneskens, L. W. J. Phys. Chem. A 2001, 105, 3838-3845.
16. Havenith, R. W. A.; Jiao, H.; Jenneskens, L. W.; van Lenthe, J. H.; Sarobe, M.; Schleyer, P. v. R.; Necula, A.; Scott, L. T.; Kataoka, M. J. Am. Chem. Soc. 2002, 124, 2363-2370.
17. Steiner, E.; Fowler, P. W.; Jenneskens, L. W.; Havenith, R. W. A. Eur. J. Org. Chem. 2002, 163-169.
18. Subramanian, G.; Schleyer, P. v. R.; Jiao, H. Angew. Chem., Int. Ed. Engl. 1996, 35, 2638-2641.
19. Sarobe, M.; Flink, S.; Jenneskens, L. W.; Zwikker, J. W.; Wesseling, J. J. Chem. Soc., Perkin Trans. 2 1996, 2125-2131.
20. Brown, R. F. C.; Eastwood, F. W.; Wong, N. R. Tetrahedron Lett. 1993, 34, 1223-1226.
21. CP-PAHs 1-3, 5, and 6 are also of interest as combustion effluents due to their genotoxic properties. See for a recent paper: Otero-Lobato, M. J.; Jenneskens, L. W.; Seinen, W. Environ. Mol. Mutagen. 2004, 44, 304-312.
22. Fowler, P. W.; Zanasi, R.; Cadioli, B.; Steiner, E. Chem. Phys. Lett. 1996, 251, 132-140.
23. Fowler, P. W.; Steiner, E.; Acocella, A.; Jenneskens, L. W.; Havenith, R. W. A. J. Chem. Soc., Perkin Trans. 2 2001, 1058-1065.
24. Havenith, R. W. A.; Jenneskens, L. W.; Fowler, P. W.; Steiner, E. Phys. Chem. Chem. Phys. 2004, 6, 2033-2039.
25. Poater, J.; Solà, M.; Viglione, R. G.; Zanasi, R. J. Org. Chem. 2004, 69, 7537-7542.
26. Cooper, D. L.; Gerratt, J.; Raimondi, M. Nature 1986, 323, 699-701.
27. Sironi, M.; Cooper, D. L.; Gerratt, J.; Raimondi, M. J. Chem. Soc., Chem. Commun. 1989, 675-677.
28. Guest, M. F.; van Lenthe, J. H.; Kendrick, J.; Schöffel, K.; Sherwood, P. GAMESS-UK, a package of ab initio programs, 2000.
29. With contributions from Amos, R. D.; Buenker, R. J.; van Dam, H. J. J.; Dupuis, M.; Handy, N. C.; Hillier, I. H.; Knowles, P. J.; Bonacic-Koutecky, V.; von Niessen, W.; Harrison, R. J.; Rendell, A. P.; Saunders, V. R.; Stone, A. J.; Tozer, D. J.; de Vries, A. H. It is derived from the original GAMESS code due to M. Dupuis, D. Spangler, and J. Wendolowski. NRCC Software Catalog, Vol. 1, program no. QG01 (GAMESS), 1980.
30. Verbeek, J.; Langenberg, J. H.; Byrman, C. P.; Dijkstra, F.; Engelberts, J. J.; van Lenthe, J. H. TURTLE, an ab initio VB/VBSCF program, 1988-2005.
31. Saunders, V. R.; Guest, M. F. Atmol Program Package; SERC Daresbury Laboratorium: Daresbury, Great Britain.
32. Chirgwin, B. H.; Coulson, C. A. Proc. R. Soc. London A 1950, 201, 196-209.
33. Dijkstra, F.; van Lenthe, J. H. J. Comput. Chem. 2001, 22, 665-672.
34. Löwdin, P. O. Rev. Mod. Phys. 1967, 39, 259.
35. Fries, K. Justus Liebigs Ann. Chem. 1927, 454, 121-324.
36. Randić, M.; Pisanski, T. Rep. Mol. Theory 1990, 1, 107-114.
37. Mo, Y.; Jiao, H.; Lin, Z.; Schleyer, P. v. R. Chem. Phys. Lett. 1998, 289, 383-390.
38. Schleyer, P. v. R.; Pühlhofer, F. Org. Lett. 2002, 4, 2873-2876.
39. Plavšić, D.; Nikolić, S.; Trinajstić, N. J. Mol. Struct. (THEO-CHEM) 1992, 277, 213-237.
40. Diogo, H. P.; Kiyobayashi, T.; Minas da Piedade, M. E.; Burlak, N.; Rogers, D. W.; McMasters, D.; Persy, G.; Wirz, J.; Liebman, J. F. J. Am. Chem. Soc. 2002, 124, 2065-2072.
41. Koper, C.; Sarobe, M.; Jenneskens, L. W. Phys. Chem. Chem. Phys. 2004, 6, 319-327.