Transition State Structure for the Water-Catalyzed Hydrolysis of p-Nitrophenyl Trifluoroacetate in Acetonitrile

Journal of Organic Chemistry

Volumn 63, Issue 18, 1998, Pages 6115-6118

  Venkatasubban, K S ^a   Bush, Melissa ^a   Ross, Eileen ^a   Schultz, Michael ^a   Garza, Oscar ^a  

^a UNIVERSITY OF NORTH FLORIDA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0040560231     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo972027f     Document Type: Article

References (21)

1. Bell, R. P.; Critchlow, J. E. Proc. R. Soc. London, Ser. A. 1971, 325, 35-55.
2. Wolfe, S.; Kim, C. K.; Yang, K.; Weinberg, N.; Shi, Z. J. Am. Chem. Soc. 1995, 117, 4240-4260.
3. Venkatasubban, K. S.; Davis, K. R.; Hogg, J. L. J. Am. Chem. Soc. 1978, 100, 6125.
4. Venkatasubban, K. S.; Silverman, D. N. Biochemistry 1980, 19, 4984.
5. Cleland, W. W.; Kreevoy, M. M. Science 1994, 264, 1887.
6. (a) Steigman; Hammett. J. Am. Chem. Soc. 1937, 59, 2536.
7. (b) Farinacci; Hammett. J. Am. Chem. Soc. 1937, 59, 2542.
8. Venkatasubban, K. S.; Schowen, R. L. CRC Crit. Rev. Biochem. 1984, 17, 1-44.
9. (a) Gross, P. Z. Electrochem. 1938, 44, 299-301.
10. (b) Orr, W. J. C.; Butler, J. A. V. J. Chem. Soc. 1937, 330-335.
11. Kresge, A. J. Pure Appl. Chem. 1964, 8, 243-258.
12. Gold, V. Adv. Phys. Org. Chem. 1969, 7, 259-331.
13. Kresge, A. J.; More O'Ferall, R. A.; Powell, M. S. In Isotopes in Organic Chemistry; Buncel, E., Lee, C. C., Eds.; Elsevier: 1987; Vol. 1, p 7.
14. (a) Schowen, R. L. In Isotope Effects on Enzyme-Catalyzed Reactions; Cleland, W. W., O'Leary, M. H., Northrop, D. B., Eds.; university Park Press: Baltimore, 1972; p 64.
15. (b) Schowen, K. B.; Schowen, R. L. Methods Enzymol. 1982, 87C, 551.
16. (c) Schowen, K. B. In Transition States of Biochemical Process; Gandour, R. B., Schowen, R. L., Eds.; Plenum Press: New York, 1978; p 255.
17. Albery, W. J.; Davies, M. H. J. Chem. Soc. Faraday Trans. 1972, 167.
18. Eigen, M. Discuss. Faraday Soc. 1965, 39, 7-15.
19. Cox, R. A. Can. J. Chem. 1996, 74, 1779-83.
20. Gandour, R. D. Tetrahedron Lett. 1974, 295-298.
21. We thank one of the reviewers for suggesting this plot.