Direct evaluation of cyclic contributions to the π energy of conjugated hydrocarbons from strongly localized zero-order pictures

Journal of Physical Chemistry A

Volumn 112, Issue 50, 2008, Pages 13203-13214

  Malrieu, Jean Paul ^a   Giequel, Mickaël ^b   Fowler, Patrick W ^c   Lepetit, Christine ^b   Heully, Jean Louis ^a   Chauvin, Remi ^b  

^a Université Paul Sabatier   (France)

^b CNRS   (France)

^c UNIVERSITY OF SHEFFIELD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ATOMS; BENZENE; BUTADIENE; CHEMICAL REACTIONS; FUNCTIONS; HYDROCARBONS; ISOMERS; MOLECULAR GRAPHICS; OPEN SYSTEMS; ORGANIC COMPOUNDS;

AROMATICITY; AROMATICITY INDICES; CHEMICAL EQUATIONS; CYCLIC ENERGIES; CYCLOBUTADIENE; DOUBLE BONDS; ELECTRONIC ENERGIES; GENERAL EXPRESSIONS; HETERO SUBSTITUTED; HOPPING INTEGRALS; MOLECULAR GRAPHS; RING SIZES; SECOND ORDERS; SINGLE BONDS; SUB SYSTEMS; THIRD ORDERS;

CHEMICAL BONDS;

EID: 58149168708     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp802839n     Document Type: Article

References (30)

1. For reviews see:(a) Schleyer, P; von, R.; Jiao, H. PureAppI, Chem. 1996, 68, 209.
2. (b) Minkin, V. I.; Gluckhovtsev, M. N.; Simkin, B. Y. In Aromaticity and Antiaromaticity, Electronic and Structural Aspects; Wiley: New York, 1994.
3. (c) Katritsky, A. R.; Barezvnski, P.; Musumarra, G.; Pisano, D.; Szafran, M. J. Am. Chem. Soc. 1989, m, 7.
4. (d) Zou, C.; Lepetit, C.; Coppel, Y.; Chauvin, R. Pure Appl. Chem. 2006, 78, 791.
5. (e) Special issues of Chem. Rev. 2001, 101, and 2005, 105.
6. (a) Hehre, W. J.; Dichtfield, R.; Radom, L.; Pople, J. A. J. Am. Chem. Soc. 1970, 92, 4796.
7. (b) George, P.; Trachtman, M.; Bock, C. W.; Brett, A. M. /. Chem. Soc, Perkin Trans. 2 1976, 1222.
8. (c) George, P.; Trachtman, M.; Bock, C. W.; Brett, A. M. Tetrahedron 1976, 32, 317.
9. (d) Hess, B. A., Jr.; Schaad, L. J. J. Am. Chem. Soc. 1983, 105, 7500.
10. (e) Cyranski, M. K. Chem. Rev. 2005, 105, 3773.
11. (a) Lazzeretti, P. Prog. Nucl. Magn. Reson. Spectrosc. 2000, 36, 1.
12. (b) Heine, T.; Corminboeuf, C.; Seifert, G. Chem. Rev. 2005, 105, 3889.
13. (c) Geuenich, D.; Hess, K.; Köhler, F.; Herges, R. Chem. Rev. 2005, 105, 3758, and references therein.
14. Santos, J. C.; Andres, J.; Aizman, A.; Fuentealba, P. J. Chem. Theory Comput. 2005, 1, 83.
15. Shurki, A.; Hibertv, P. C.; Dijkstra, F.: Shaik, P. J. Phys. Org. Chem. 2003, 16, 731.
16. Malrieu, J.-P.; Lepetit, C.; Gicquel, M.; Heully, J.-L.; Fowler, P. W.; Chauvin, R. New J. Chem. 2007, 31, 1918.
17. (a) Breslow, R.; Mohacsi, E. J. Am. Chem. Soc. 1963, 85, 431.
18. (b) Aihara, J.-L; Ichikawa, H. Bull. Chem. Soc. Jpn. 1988, 61, 223.
19. Malrieu, J. P.; Robert, V. J. Phys. Org. Chem. 2005, 19, 10.
20. Jug, K.; Hiberty. P. C.; Shaik. S. Chem. Rev. 2001, 101, 1477.
21. Malrieu, J. P.; Maynau, D. J. Am. Chem. Soc. 1982, 104, 3021.
22. Daudey, J. P.; Heully, J. L.; Malrieu, J. P. J. Phys. Chem. 1993, 99, 1240.
23. The reader may find a presentation of the Feynman diagrams employed here in Szabo, A.; Ostlund, N. Modern Quantum Chemistrx; McGraw Hill: New York, 1989.
24. Shurki, A.; Hibertv. P. C.; Dijkstra. F.; Shaik. S. J. Phys. Org. Chem. 2003, 16, 731.
25. Goldstone, J. Proc. R. Soc. London, Ser. A 1957, 239, 267.
26. (a) Havenith, R. W. A.; Jenneskens, L W.; Fowler, P. W. Chem. Phys. Lett. 2003, 367, 468.
27. (b) Soncini, A.; Havenith, R. W. A; Fowler, P. W.; Jenneskens, L. W.; Sterner, E. J. Org. Chem. 2002, 67, 4753.
28. (a) Hibertv, P. C.; Shaik, S. Phys. Chem. Chem. Phys. 2004, 6, 224.
29. (b) Shaik, S.; Shurki, A.; Danovich, D.; Hibertv, P. C. J. Mol. Struct. (THEOCHEM) 1997, 398-399, 155.
30. Angeli, C.; Malrieu, J. P. J. Phys. Chem. A, in press.