Recommendations for the evaluation of aromatic stabilization energies

Organic Letters

Volumn 4, Issue 17, 2002, Pages 2873-2876

  Von Ragué Schleyer, Paul ^a,b   Puhlhofer, Frank ^a,b  

^a UNIVERSITY OF GEORGIA   (United States)

^b UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0041689490     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0261332     Document Type: Article

References (20)

1. Wheland, G. W. Resonance in Organic Chemistry; Wiley: New York, 1955.
2. (a) Pedley J. B.; Naylor R. D.; Kirby S. P. Thermochemical Data of Organic Compounds; Chapman and Hall: London, 1986; p 87ff.
3. (b) Afeefy, H. Y.; Liebman, J. F.; Stein, S. E. Neutral Thermochemical 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: July 2001 (http://webbook.nist.gov).
4. Dewar, M. J. S.; Schmeising, H. N. Tetrahedron 1959, 5, 166.
5. (a) Schleyer, P. v. R.; Manoharan, M.; Jiao H.; Stahl, F. Org. Lett. 2001, 3, 3643.
6. (b) See Suresh, C. H.; Koga, N. J. Org. Chem. 2002, 67, 1965, for another approach giving SE = 29 kcal/mol for benzene.
7. Cyrañski, M. K.; Krygowski, T. M.; Katritzky, A. R.; Schleyer P. v. R. J. Org. Chem. 2002, 67, 1338.
8. Sauers, R. R. et al. Manuscript in preparation.
9. All energies refer to minima optimized in their most stable geometries at B3LYP/6-311+G** using Gaussian 98 (Frisch, M. J. et al., Revision A.5; Gaussian, Inc.: Pittsburgh, PA, 1998). Zero-point energies computed at B3LYP/6-31G* were applied.
10. Minkin, V. J.; Glukhovtsev, M. N.; Simkin, B. Y. Aromaticity and Antiaromaticity: Electronic and Structural Aspects; Wiley: New York, 1994; p 80.
11. (a) Wakita, K.; Tokitoh, N.; Okazaki, R.; Nageses, S.l Scheyer, P. v. R.; Jiao, H. J. Am. Chem. Soc. 1999, 121, 11336.
12. (b) Havenith, R. W. A.; Jiao, H.; Jenneskens, W.; van Lenthe, J. H.; Sarobe, M.; Schleyer, P. v. R.; Kataoka, M.; Necula, A.; Scott, L. T. J. Am. Chem. Soc. 2002, 124, 2363. The ISE corrections recommended in the present paper were not applied in these publications or in ref 4a.
13. (a) Vogel, E.; Roth, H. D. Angew. Chem. 1964, 76, 145; Angew. Chem., Int. Ed. Engl. 1964, 3, 228.
14. (a) Vogel, E.; Roth, H. D. Angew. Chem. 1964, 76, 145; Angew. Chem., Int. Ed. Engl. 1964, 3, 228.
15. (b) Jiao, H.; Hommes, N. J. R. v. E.; Schleyer, P. v. R. Org. Lett., submitted.
16. Rice, J. E.; Lee, T. J.; Remington, R. B.; Allen, W. D.; Clabo, D. A.; Schaefer, H. F. J. Am. Chem. Soc. 1987, 109, 2902.
17. 10 8 (-13.5/-7.5; into/out of cage), and 9 (-12.2).
18. Boydston, A. J.; Haley, M. M. Org. Lett. 2001, 3, 3599.
19. Schleyer, P. v. R. et al. Unpublished data.
20. 1 point group), preoptimization at semiempirical or other lower levels is recommended. As was done here, vibrationat frequencies and the derived ZPEs also can be from lower levels.