Electronic factors influencing the decarboxylation of β-keto acids. A model enzyme study

Journal of Organic Chemistry

Volumn 61, Issue 18, 1996, Pages 6346-6353

  Bach, Robert D ^a   Canepa, Carlo ^a  

^a WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84961974526     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960356m     Document Type: Article

References (29)

1. Logue, M. W.; Pollack, R. M.; Vitullo, V. P. J. Am. Chem. Soc. 1875, 97, 6868.
2. Walsh, C. Enzymatic Reaction Mechanism; W. H. Freeman and Co.: New York, 1979.
3. Skorcz, J. A.; Kaminski, F. E. Org. Synth. 1988, 48, 53.
4. Steinberger, R.; Westheimer, F. H. J. Am. Chem. Soc. 1951, 73, 429.
5. Straub, T. S.; Bender, M. L. J. Am. Chem. Soc. 1972, 94, 8881.
6. Swain, C. G.; Bader, R. F. W.; Esteve, R. M., Jr.; Griffin, R. N. J. Am. Chem. Soc. 1961, 83, 1951.
7. Westheimer, F. H.; Jones, W. A. J. Am. Chem. Soc. 1941, 63, 3283.
8. Pedersen, K. J. J. Phys. Chem. 1934, 38, 559.
9. Hine, J. Physical Organic Chemistry; McGraw-Hill: New York, 1952.
10. Bigley, D. B.; Thurman, J. C. J. Chem. Soc. B 1968, 436.
11. Miyamoto, K.; Tsuchiya, S.; Ohta, H. J. Am. Chem. Soc. 1992, 114, 6256.
12. Kim, Y. S.; Kolattukudy, P. E. J. Biol. Chem. 1980, 255, 686.
13. (a) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowki, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. GAUSSIAN 94, Gaussian, Inc., Pittsburgh, PA, 1995.
14. (b) Gonzalez, C.; Schlegel, H. B. J. Chem. Phys. 1989, 90, 2154.
15. (c) Miertus, S.; Scrocco, E.; Tomasi, J. Chem. Phys. 1981, 55, 117.
16. Gandour, R. D. Tetrahedron Lett. 1974, 3, 295.
17. Hall, G. A., Jr. J. Am. Chem. Soc. 1949, 71, 2691.
18. Hall, G. A., Jr.; Hanrahan, E. S. J. Phys. Chem. 1965, 69, 2402.
19. Miyamoto, K.; Ohta, H. J. Am. Chem. Soc. 1990, 112, 4077.
20. Thomas, N. R.; Rose, J. E.; Gani, D. J. Chem. Soc., Chem. Commun. 1991, 908.
21. Ferris, J. P.; Miller, N. C. J. Am. Chem. Soc. 1966, 88, 3522.
22. The activation barrier of this decarboxylation reaction has been recomputed both at the MP2/6-31G* and RHF/6-31+G* levels to assess the effect of diffuse functions in the basis set and the electronic correlation, respectively. Diffuse functions show minimal effect on the barrier, the latter being dimished by only 0.4 kcal/mol. The HF/6-31+G* barrier increased by 5.5 kcal/mol with respect to the MP2/6-31+G*.
23. Breneman, C. M.; Wiberg, K. B. J. Comput. Chem. 1990, 11, 361.
24. Corey, E. J.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1965, 4, 1075.
25. Bach, R. D.; Su, M.-D. J. Am. Chem. Soc. 1994, 116, 5392.
26. van Poelje, P. D.; Snell, E. E. Ann. Rev. Biochem. 1990, 59, 29.
27. Hayashi, H.; Mizuguchi, H.; Kagamiyama, H. Biochemistry 1993, 32, 812.
28. Tonety M. D.; Hohenester, E.; Keller, J. W.; Jansonius, J. N. J. Mol. Biol. 1995, 245, 151.
29. Gonzalez, C.; Schlegel, H. B. J. Phys. Chem. 1990, 94, 5523.