On the stability of large [4n]annulenes

Organic Letters

Volumn 5, Issue 17, 2003, Pages 2983-2986

  Wannere, Chaitanya S ^a   Moran, Damian ^a   Allinger, Norman L ^a   Hess Jr , B Andes ^b   Schaad, Lawrence J ^b   Schleyer, Paul Von Ragué ^a  

^a UNIVERSITY OF GEORGIA   (United States)

^b VANDERBILT UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 BUTADIENE; ANNULENE DERIVATIVE; INDENE DERIVATIVE;

ARTICLE; CONFORMATION; ELECTRON;

EID: 0141521437     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034979f     Document Type: Article

References (43)

1. Streitwieser, A., Jr. Molecular Orbital Theory for Organic Chemists; John Wiley: New York, 1961.
2. (a) Breslow, R. Chem. Eng. News 1965, 43, 90.
3. (b) Dewar, M. J. S. Adv. Chem. Phys. 1965, 8, 65.
4. Breslow, R. Acc. Chem. Res. 1973, 6, 393.
5. Wiberg, K. B. Chem. Rep. 2001, 101, 1317.
6. (a) Minkin, V. I.; Glukhovtsev, M. N.; Simkin, B. Y. Aromaticity and Antiaromaticity. Electronic and Structural Aspects; John Wiley & Sons: New York, 1994.
7. (b) Dewar, M. J. S.; de Llano, C. J. Am. Chem. Soc. 1969, 91, 789.
8. (c) Schaad, L. J.; Hess, B. A., Jr. Chem. Rev. 2001, 101, 1465.
9. (d) Hess, B. A., Jr.; Schaad, L. J. J. Am. Chem. Soc. 1971, 93, 305.
10. Klärner, F.-G. Angew. Chem., Int. Ed. 2001, 40, 3977.
11. (a) Anet, F. A. L. J. Am. Chem. Soc. 1962, 84, 671.
12. (b) Anet, F. A. L.; Bourn, A. J. R.; Lin, Y. S. J. Am. Chem. Soc. 1964, 86, 3576.
13. (c) Oth, J. F. M. Pure Appl. Chem. 1971, 25, 573.
14. (d) Luz, Z.; Meiboom, S. J. J. Chem. Phys. 1973, 59, 1077.
15. (e) Naor, R.; Luz, Z. J. Chem. Phys. 1982, 76, 5662.
16. Krygowski, T. M.; Pindelska, E.; Cyrañski, M. K.; Häfelinger, G. Chem. Phys. Lett. 2002, 359 (1-2), 158.
17. (a) Allinger, N. L.; Sprague, J. T.; Finder, C. J. Tetrahedron, 1973, 29, 2519.
18. (b) Roth, W. R.; Lennartz, H.-W.; Vogel, E.; Leiendecker, M.; Oda. M. Chem. Ber. 1986, 119, 837.
19. (c) Nevins, N.; Lii, J. H.; Allinger, N. L. J. Comput. Chem. 1996, 17, 695.
20. Schleyer, P. v. R.; Pühlhofer, F. Org. Lett. 2002, 4, 2873.
21. Details of the correction evaluations are explained fully in Supporting Information.
22. When fused to an arene, the cyclopentene moiety is taken by our convention to have a syn conformation irrespective of the Kekulé form of the aromatic ring.
23. (a) Syn-anti corrections for SP's ISE method were evaluated as the energy difference between the dihydrogen derivative of methyl-[4n]-annulene and their respective nonaromatic isomer.
24. s geometries optimized at B3LYP/6-31G* using Gaussian 98 (reference in Supporting Information). Zero-point energies computed at B3LYP/6-31G* were applied.
25. (a) Pedley J. B.; Naylor R. D.; Kirby S. P. Theromochemical Data of Organic Compounds; Chapman and Hall: London, 1986.
26. (b) Afeefy, H. Y.; Liebman, J. F.; Stein, S. E. Neutral Theromochemical Data. In NIST Chemistry WebBook, NIST Standard Reference Database No. 69; Linstrom, P. J., Mallard, W. G., Eds.; National Institute of Standards and Technology: Gaithersburg, MD; http://webbook.nist.gov (accessed July 2001).
27. Wannere, C. S.; Schleyer, P. v. R. Org. Lett. 2003, 5, 865.
28. Dewar M. J. S.; Dougherty R. C. The PMO Theory of Organic Chemistry; Plenum: New York, 1975.
29. (a) Baldridge, K. K.; Siegel, J. S. Angew. Chem., Int. Ed. Engl. 1997, 36, 745.
30. (b) Choi, C. H.; Kertesz, M. J. Chem. Phys. 1998, 108, 6681.
31. (a) Murray, J. S.; Seminario, J. M.; Politzer, P. Int. J. Quantum Chem. 1994, 49, 575.
32. (b) Politzer, P.; Murray, J. S.; Seminario, J. M. Int. J. Quantum Chem. 1994, 50, 273.
33. (a) Dauben, H. J.; Wilson, J. D.; Laity, J. L. Nonbenzenoid Aromaticity Snyder, J. P., Eds.; Academic Press: New York, 1971; Vol 2, and references therein.
34. (b) Jiao, H.; Schleyer, P. v. R. Angew. Chem., Int. Ed. Engl. 1993, 32, 1763.
35. (c) Herges, R.; Jiao, H.; Schleyer, P. v. R. Angew. Chem., Int. Ed. Engl. 1994, 33, 1376.
36. (d) Schleyer, P. v. R.; Jiao, H. Pure Appl. Chem. 1996, 68, 209.
37. (a) Schleyer, P. v. R.; Maerker, C.; Dransfeld, A.; Jiao, H.; Hommes, N. J. R. v. E. J. Am. Chem. Soc. 1996, 118, 6317.
38. (b) Schleyer, P. v. R.; Jiao, H.; Hommes, N. J. R. v. E.; Malkin, V. G.; Malkina, O. L. J. Am. Chem. Soc. 1997, 119, 12669.
39. (c) Schleyer, P. v. R.; Manoharan, M.; Wang, Z. X.; Kiran, B.; Jiao, H.; Puchta, R.; Hommes, N. J. R. v. E. Org. Lett. 2001, 3, 2465.
40. 2= and =CH- increments are -7.3 and -5.1 cgs ppm, respectively.
41. Wannere, C. S.; Schleyer, P. v. R. Org. Lett. 2003, 5, 605.
42. Negative value of absolute magnetic shieldings calculated at revealing points (generally center of the ring) in [n]annulene system.
43. Such conclusions also were made from a study of aromatic systems comprised of 105 compounds. For example, see: Cyrañski, M. K.; Krygowski, T. M.; Katritzky, A. R.; Schleyer, P. v. R. J. Org. Chem. 2002, 67, 1333.