Aromaticity: An ab initio evaluation of the properly cyclic derealization energy and the π-delocalization energy distortivity of benzene

Journal of Physical Chemistry A

Volumn 112, Issue 45, 2008, Pages 11481-11486

  Angeli, Celestino ^a   Malrieu, Jean Paul ^b  

^a UNIVERSITY OF FERRARA   (Italy)

^b UNIVERSITÉ PAUL SABATIER   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ATOMIC PHYSICS; ATOMS; BENZENE; CHEMICAL BONDS; MOLECULAR GRAPHICS; MOLECULAR ORBITALS; ORGANIC POLYMERS; QUANTUM CHEMISTRY;

AB INITIO; AROMATICITY; BENZENE RINGS; BOND ALTERNATIONS; CARBON ATOMS; CAS-SCF; COMPLETE ACTIVE SPACES; CONJUGATED MOLECULES; CYCLIC CORRELATIONS; DELOCALIZATION; DELOCALIZATION ENERGIES; ELECTRON DEREALIZATIONS; ELECTRONIC CORRELATIONS; ENERGY CONTRIBUTIONS; SELF-CONSISTENT FIELDS; THIRD ORDERS;

FREE RADICALS;

EID: 57149111528     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp805870r     Document Type: Article

References (45)

1. (a) For reviews see: Schleyer, P.; von, R.; Jiao, H. Pure Appl. 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.; Barczynski, P.; Musumarra, G.; Pisano, D.; Szafran, M. J. Am. Chem. Soc. 1989, 111, 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) Lazzeretti, P. Prog. Nucl. Magn. Reson. Spectrosc. 2000, 36, 1.
7. (b) Heine, T.; Corminboeuf, C.; Seifert, G. Chem. Rev. 2005, 105, 3889.
8. (c) Geuenich, D.; Hess, K.; Köhler, F.; Herges, R. Chem. Rev 2005, 105, 3758, and references therein.
9. (a) Hehre, W. J.; Dichtfield, R.; Radom, L.; Pople, J. A. J. Am. Chem. Soc. 1970, 92, 4796.
10. (b) George, P.; Trachtman, M.; Bock, C. W.; Brett, A. M. J. Chem. Soc., Perkin Trans. 2 1976, 1222.
11. (c) George, P.; Trachtman, M.; Bock, C. W.; Brett, A. M. Tetrahedron 1976, 32, 317.
12. (d) Hess, B. A., Jr.; Schaad, L. J. J. Am. Chem. Soc. 1983, 105, 7500.
13. (e) Cyranski, M. K. Chem. Rev. 2005, 105, 3773.
14. (a) Breslow, R.; Mohacsi, E. J. Am. Chem. Soc 1963, 85, 431.
15. (b) Aihara, J.-I.; Ichikawa, H. Bull. Chem. Soc. Jpn. 1988, 61, 223.
16. Malrieu, J.-P.; Lepetit, C.; Gicquel, M.; Heully, J.-L.; Fowler, P. W.; Chauvin, R. New J. Chem. 2007, 31, 1918.
17. Malrieu, J.-P.; Gicquel, M.; Fowler, P. W.; Lepetit, C.; Heully, J.-L.; Chauvin, R. J. Phys. Chem. A, in press.
18. (a) Ruedenberg, K.; Schmidt, M. W.; Gilbert, M. M.; Elbert, S. T. Chem. Phys. 1982, 71, 41.
19. (b) Ruedenberg, K.; Schmidt, M. W.; Gilbert, M. M.; Elbert, S. T. Chem. Phys. 1982, 71, 51.
20. (c) Ruedenberg, K.; Schmidt, M. W.; Gilbert, M. M.; Elbert, S. T. Chem. Phys. 1982, 71, 65.
21. (a) Maynau, D.; Evangelisti, S.; Guihéry, N.; Calzado, C. J.; Malrieu, J.-P J. Chem. Phys. 2002, 116, 10060.
22. (b) Angeli, C.; Evangelisti, S.; Maynau, D.; Cimiraglia, R. J. Chem. Phys. 2002, 117, 10525.
23. (a) Malrieu, J.-P.; Guihéry, N.; Angeli, C.; Calzado, C. J. J. Comput. Chem. 2007, 28, 35.
24. (b) Angeli, C.; Cimiraglia, R.; Malrieu, J.-P. J. Chem. Educ. 2008, 85, 150.
25. McWeeny, R. Proc. Phys. Soc. London A 1953, 66, 714.
26. Bernhardsson, A.; Forsberg, N.; Malmqvist, P.-Å; Roos, B. O. J. Chem. Phys. 2000, 112, 2798.
27. Widmark, P.-O.; Malmqvist, P.-Å.; Roos, B. O. Theor. Chim. Acta 2000, 77, 291.
28. (a) Hiberty, P. C.; Shaik, S.; Lefour, J. M.; Ohanessian, G. J. Org. Chem. 1985, 50, 4657.
29. (b) Shaik, S.; Hiberty, P. C. J. Am Chem. Soc. 1985, 107, 3089.
30. (c) Hiberty, P. C.; Shaik, S.; Ohanessian, G.; Lefour, J. M. J. Org. Chem. 1986, 51, 3908.
31. (d) Shaik, S.; Hiberty, P. C.; Lefour, J. M.; Ohanessian, G. J. Am. Chem. Soc. 1987, 109, 363.
32. (e) Shaik, S.; Hiberty, P. C.; Ohanessian, G.; Lefour, J. M. J. Phys. Chem. 1988, 92, 5086.
33. (f) Hiberty, P. C.; Danovich, D.; Shurki, A.; Shaik, S. J. Am. Chem. Soc. 1995, 117, 7760.
34. (g) Shurki, A.; Shaik, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2205.
35. (h) Shaik, S.; Shurki, A.; Danovich, D.; Hiberty, P. C. Chem. Rev. 2001, 101, 1501.
36. (a) Jug, K.; Koster, A. M. J. Am. Chem Soc. 1990, 112, 6772.
37. (b) Gobbi, A.; Yamaguchi, Y.; Frenking, G.; Schaefer, H. F., III Chem. Phys. Lett. 1995, 244, 27.
38. (c) Kovačević, B.; Barić, D.; Maksić, Z. B.; Müller, T. ChemPhysChem 2004, 5, 1352.
39. (d) Rehaman, A.; Datta, A.; Mallajosyula, S. S.; Pati, S. K. J. Chem. Theory Comput. 2006, 2, 30.
40. The reader may find a presentation of the here-employed Feynman diagrams in: Szabo, A.; Ostlund, N. Modern Quantum Chemistry; McGraw Hill: New York, 1989.
41. Daudey, J. P.; Heully, J. L.; Malrieu, J.-P. J. Phys. Chem. 1993, 99, 1240.
42. Shurki, A.; Hiberty, P. C.; Dijkstra, F.; Shaik, S. J. Phys. Org. Chem. 2003, 16, 731.
43. Maynau, D.; Malrieu, J.-P. J. Am. Chem Soc. 1982, 104, 3029.
44. (a) Havenith, R. W. A.; Jenneskens, L. W.; Fowler, P. W. Chem. Phys. Lett. 2003, 367, 468.
45. (b) Soncini, A.; Havenith, R. W. A.; Fowler, P. W.; Jenneskens, L. W.; Steiner, E. J. Org. Chem. 2002, 67, 4753.