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Volumn 94, Issue 1, 1972, Pages 71-75

Enhancement of Saponification Rates in Aqueous Dipolar Solvents. Hydroxide Ion Solvation vs. Transition State Solvation

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EID: 33947091752     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00756a013     Document Type: Article
Times cited : (43)

References (31)
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    • J. Org. Chem., 29, 2716 (1964)
    • (1964) J. Org. Chem. , vol.29 , pp. 2716
  • 5
    • 0001427207 scopus 로고
    • J. Org. Chem., 30, 3516 (1965)
    • (1965) J. Org. Chem. , vol.30 , pp. 3516
  • 11
    • 0006215391 scopus 로고
    • E. g., see, and references cited therein
    • E. g., see G. Choux and R. L. Benoit, J. Amer. Chem. Soc., 91, 622 (1969), and references cited therein.
    • (1969) J. Amer. Chem. Soc. , vol.91 , pp. 622
    • Choux, G.1    Benoit, R.L.2
  • 26
    • 0001186521 scopus 로고
    • This is a fairly reasonable assumption, found from the hydrolysis and carbonyl oxygen exchange rates in the base-catalyzed hydrolysis of ethyl benzoate in 33 % dioxane-H2O that the energy of activation for the hydrolysis reaction, Eh = 12. 9 kcal/mol; and the activation energy for the first step in the reaction, E1 = 13. 2 kcal/mol
    • This is a fairly reasonable assumption. M. L. Bender, R. D. Ginger, and J. P. Unik [J. Amer. Chem. Soc., 80, 1044 (1958)] found from the hydrolysis and carbonyl oxygen exchange rates in the base-catalyzed hydrolysis of ethyl benzoate in 33 % dioxane-H2O that the energy of activation for the hydrolysis reaction, Eh = 12. 9 kcal/mol; and the activation energy for the first step in the reaction, E1 = 13. 2 kcal/mol.
    • (1958) J. Amer. Chem. Soc. , vol.80 , pp. 1044
    • Bender, M.L.1    Ginger, R.D.2    Unik, J.P.3
  • 27
    • 5244245983 scopus 로고
    • This is what would be expected
    • This is what would be expected from Hammondʼns postulate: G. S. Hammond, J. Amer. Chem. Soc., 77, 334 (1955).
    • (1955) J. Amer. Chem. Soc. , vol.77 , pp. 334
    • Hammond, G.S.1
  • 29
    • 0008517981 scopus 로고
    • W. D. McElroy and B. Glass, Ed., Johns Hopkins Press, Baltimore, Md.
    • H. Eyring, R. Lumry, and J. D. Spikes, “The Mechanism of Enzyme Action,” W. D. McElroy and B. Glass, Ed., Johns Hopkins Press, Baltimore, Md., 1954, p 123.
    • (1954) The Mechanism of Enzyme Action , pp. 123
    • Eyring, H.1    Lumry, R.2    Spikes, J.D.3
  • 30
    • 85023270125 scopus 로고    scopus 로고
    • For a discussion and references see ref 6a
    • For a discussion and references see ref 6a, pp 242–258.


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