Strain release is not enough

Tetrahedron Letters

Volumn 37, Issue 31, 1996, Pages 5573-5576

  Sella, Ariel ^a   Basch, Harold ^a   Hoz, Shmaryahu ^a  

^a BAR ILAN UNIVERSITY   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; CHEMICAL REACTION KINETICS; MOLECULAR DYNAMICS; THERMODYNAMICS;

EID: 0030605831     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01128-8     Document Type: Article

References (11)

1. 1. (a). Greenberg, A.; Liebman, J. F. "Strained Organic Molecules": Academic Press, New York, 1978;
2. (b) Wiberg, K. B. Angew. Chem. Int. Ed. Engl. 1986, 25, 312;
3. (c) Advances in Strain in Organic Chemistry, Volume 1, Halton, B. Ed.; JAI Press, London, 1991.
4. 2. Sella, A.; Basch, H.; Hoz, S. J. Am. Chem. Soc. 1996, 118, 416.
5. 3. Kaszynski, P.; Michl, J. in "The Chemistry of the Cyclopropyl Group", Rappoport Z. Ed.; John Wiley & Sons, 1995, Chapter 11.
6. 4. Kaszynski, P.; Michl, J. J. Am. Chem. Soc. 1988, 110, 5225; Optiz, K.; Schluter, A. -D. Angew. Chem. Int. Ed. Engl. 1989, 28, 456
7. 4. Kaszynski, P.; Michl, J. J. Am. Chem. Soc. 1988, 110, 5225; Optiz, K.; Schluter, A. -D. Angew. Chem. Int. Ed. Engl. 1989, 28, 456
8. 5. Gaussian 92, Revision C, Frisch, M. J.; Trucks, G. W.; Head-Gordon, M.; Gill, P. M. W.; Wong, M. W.; Foresman, J. B.; Johnson, B. G.; Schlegel, H. B.; Robb, M.A.; Replogle, E. S.; Gomperts, R.; Andres, J. L.; Raghavachari, K.; Binkley, J. S.; Gonzalez, C.; Martin, R. L.; Fox, D. J.; Defrees, D. J.; Baker, J.; Stewart, J. J. P.; Pople, J.A. Gaussian, Inc., Pittsburgh PA, 1992.
9. 2 → 1, 1, 1-bicyclopentane was calculated at both the RHF and the MP4 levels. Values of -53.2 and -40.5 kcal were obtained at the RHF/6-31+G* and the MP4/6-31+G*//6-31+G* levels respectively. The experimental values range from -39 to -34 kcal (Wiberg, K. B. J. Am. Chem. Soc. 1983, 105, 1227 and reference 1(b) respectively). The MP4 value is in a much better agreement with the experimental data, as expected. Nevertheless, it is interesting to note that the final result - the degree of strain relief at the transition state - is insensitive to the level of calculation since both methods give the same result.
10. 7. Lefller, J. E.; Grunwald, E. "Rates and Equilibria of Organic Reactions": Wiley: New York, 1963; Chapman, N.B., Shorter, J. Eds. "Correlation Analysis in Chemistry": Plenum, New York 1978.
11. 7. Lefller, J. E.; Grunwald, E. "Rates and Equilibria of Organic Reactions": Wiley: New York, 1963; Chapman, N.B., Shorter, J. Eds. "Correlation Analysis in Chemistry": Plenum, New York 1978.