-
2
-
-
77956941740
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Boyer, P. D., Ed.; Academic Press: New York, Chapter 4
-
Bruice, T. C. In The Enzymes; Boyer, P. D., Ed.; Academic Press: New York, 1970; Chapter 4, Vol. 2, p 217.
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(1970)
The Enzymes
, vol.2
, pp. 217
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-
Bruice, T.C.1
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3
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-
0342631316
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-
Van Tamelen, E. E., Ed.; Academic Press: New York, Chapter 5
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Fife, T. H. In Bioorganic Chemistry; Van Tamelen, E. E., Ed.; Academic Press: New York, 1977; Chapter 5, p 93.
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(1977)
Bioorganic Chemistry
, pp. 93
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Fife, T.H.1
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6
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0021744255
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-
(a) Hangauer, D. G.; Monzingo, A. F.; Matthews, B. W. Biochemistry 1984, 23, 5730.
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(1984)
Biochemistry
, vol.23
, pp. 5730
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Hangauer, D.G.1
Monzingo, A.F.2
Matthews, B.W.3
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9
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-
0000261801
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-
(a) Cotton, F. A.; Hazen, E. E.; Legg, M. J. Proc. Natl. Acad. Sci. USA 1979, 76, 2551.
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(1979)
J. Proc. Natl. Acad. Sci. USA
, vol.76
, pp. 2551
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Cotton, F.A.1
Hazen, E.E.2
Legg, M.3
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13
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0343501515
-
-
note
-
In comparison, appropriate intramolecular general base catalyzed hydrolysis reactions will be discussed in a following paper.
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-
-
-
16
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-
33947322034
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-
Jencks, W. P.; Gilchrist, M. J. Am. Chem. Soc. 1968, 90, 2622. Blackburn, G. M.; Jencks, W. P. J. Am. Chem. Soc. 1968, 90, 2638.
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(1968)
J. Am. Chem. Soc.
, vol.90
, pp. 2622
-
-
Jencks, W.P.1
Gilchrist, M.2
-
17
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0001361466
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-
Jencks, W. P.; Gilchrist, M. J. Am. Chem. Soc. 1968, 90, 2622. Blackburn, G. M.; Jencks, W. P. J. Am. Chem. Soc. 1968, 90, 2638.
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(1968)
J. Am. Chem. Soc.
, vol.90
, pp. 2638
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-
Blackburn, G.M.1
Jencks, W.P.2
-
23
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-
0001389531
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-
(b) Fife, T. H.; Hutchins, J. E. C.; Wang, M. S. J. Am. Chem. Soc. 1975, 97, 5878.
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(1975)
J. Am. Chem. Soc.
, vol.97
, pp. 5878
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Fife, T.H.1
Hutchins, J.E.C.2
Wang, M.S.3
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25
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0001016041
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Fife, T. H.; Bambery, R. J.; DeMark, B. R. J. Am. Chem. Soc. 1978, 100, 5500.
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(1978)
J. Am. Chem. Soc.
, vol.100
, pp. 5500
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Fife, T.H.1
Bambery, R.J.2
DeMark, B.R.3
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35
-
-
0343937354
-
-
note
-
a of the amine group would reasonably be greater than 25. A low concentration of a reactive species does not, of course, rule out a unimolecular reaction via that species if the rate constant is very large.
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-
-
-
36
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0343937353
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Unpublished data
-
0 vs pH is linear with a slope of 1.0 from pH 11.3 to 8.5 (8 points).
-
-
-
Bembi, R.1
Fife, T.H.2
-
39
-
-
0342631304
-
-
note
-
a of the leaving group.
-
-
-
-
41
-
-
0343065598
-
-
note
-
a to attack of the neutral amine at the carbonyl is highly improbable. The linear Bronsted plot of Figure 4 indicates that no change in rate-determining step occurs in the general base catalyzed cyclization of I.
-
-
-
-
42
-
-
0343937350
-
-
note
-
Values of β of 0 or 1.0 imply rate-determining proton transfer in the general base catalyzed reaction, whereas β values between 0 and 1.0 imply that bond making or breaking processes are occurring in concert with proton transfer.
-
-
-
-
43
-
-
0343065596
-
-
note
-
B[B].
-
-
-
-
44
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0000217963
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-
Fife, T. H.; Brod, L. H. J. Am. Chem. Soc. 1970, 92, 1681. Capon, B.; Nimmo, K. J. Chem. Soc., Perkin Trans. 2 1975, 1113.
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(1970)
J. Am. Chem. Soc.
, vol.92
, pp. 1681
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Fife, T.H.1
Brod, L.H.2
-
45
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37049123834
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-
Fife, T. H.; Brod, L. H. J. Am. Chem. Soc. 1970, 92, 1681. Capon, B.; Nimmo, K. J. Chem. Soc., Perkin Trans. 2 1975, 1113.
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(1975)
J. Chem. Soc., Perkin Trans. 2
, pp. 1113
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-
Capon, B.1
Nimmo, K.2
-
48
-
-
0343501506
-
-
note
-
A detailed discussion of the mechanistic differences in the intramolecular nucleophilic reactions of methyl 2-aminophenylacetate and methyl 2-aminophenylpropionate was presented in ref 20. See also references cited therein.
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-
-
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51
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0041710413
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Fife, T. H.; Jao, L. K. J. Am. Chem. Soc. 1968, 90, 4081. Fife, T. H. Acc. Chem. Res. 1972, 5, 264.
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(1968)
J. Am. Chem. Soc.
, vol.90
, pp. 4081
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Fife, T.H.1
Jao, L.K.2
-
52
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0000549918
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Fife, T. H.; Jao, L. K. J. Am. Chem. Soc. 1968, 90, 4081. Fife, T. H. Acc. Chem. Res. 1972, 5, 264.
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(1972)
Acc. Chem. Res.
, vol.5
, pp. 264
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Fife, T.H.1
-
56
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0030479175
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Fife, T. H.; Bembi, R.; Natarajan, R. J. Am. Chem. Soc. 1996, 118, 12956.
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(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 12956
-
-
Fife, T.H.1
Bembi, R.2
Natarajan, R.3
-
57
-
-
0343065592
-
-
note
-
Intramolecular nucleophilic attack does not occur via a 4-membered ring transition state in the corresponding 2-aminobenzoate esters. Fife, T.; Bembi, R. Unpublished data.
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