Acyl Transfer from Esters
Aminolysis, Imidizole Catalysis, Alcoholysis, -CO2- Attack
10. T.C. Bruice and G.L. Schmir. The Catalysis of the Hydrolysis of
p-Nitrophenyl Acetate by Imidazole and its Derivatives. Arch. Biochem.Biophys.
1956, 63, 484.
11. T.C. Bruice and G.L. Schmir. Imidazole Catalysis. I. The Catalysis
of the Hydrolysis of Phenyl Acetates by Imidazole. J.Am. Chem. Soc.
1957, 79, 1663.
13. T.C. Bruice and G.L. Schmir. Imidazole Catalysis. II. The Reaction
of Substituted Imidazoles with Phenyl Acetates in Aqueous Solution.
J. Am. Chem. Soc. 1958, 80, 148.
14. G.L. Schmir and T.C. Bruice. Imidazole Catalysis. III. The Solvolysis
of 4-(2'-Acetoxyphenyl)-imidazole. J. Am. Chem. Soc. 1958, 80, 1173.
17. T.C. Bruice and R. Lapinski, Imidazole Catalysis. IV. The Reaction
of General Bases with p-Nitrophenyl Acetate in Aqueous Solution. J.
Am. Chem. Soc. 1958, 80, 2265.
24. T.C. Bruice and M.F. Mayahi. The Influence of the Leaving Tendency
of the Phenoxy Group on the Ammonolysis and Hydrolysis of Substituted
Phenyl Acetates. J. Am. Chem Soc. 1960, 82, 3067.
25. U.K. Pandit and T.C. Bruice. Imidazole Catalysis. VII. The Dependence
of Imidazole Catalysis of Ester Hydrolysis on the Nature of the Acyl
Group. J. Am. Chem. Soc. 1960, 82, 3386.
28. T.C. Bruice and J.L. York. The Mechanism of the Reaction of Tris-(hydroxymethyl)-aminomethane
and Pentaerythritol with Phenyl Esters. J. Am. Chem. Soc. 1961, 83,
1382.
32. T.C. Bruice and J.J. Bruno. The Mechanism of the Reaction of Hydroxylamine
with ?-Butyro- and d-Valerolactones. Examples of Reactions Kenetically
both Third and Fourth Order. J. Am. Chem. Soc. 1961, 83, 3494.
35. T.C. Bruice; T.H. Fife; J.J. Bruno and N.E. Brandon. Hydroxyl Group
Catalysis. II. The Reactivity of the Hydroxyl Group of Serine. The
Nucleophilicity of Alcohols and the Ease of Hydrolysis of Their Acetyl
Esters as Related to Their pKa'. Biochem. 1962, 1, 7.
36. T.C. Bruice and F.H Marquardt. Hydroxyl Group Catalysis. IV. The
Mechanism of Intramolecular Participation of the Aliphatic Hydroxyl
Group in Amide Hydrolysis. J. Am. Chem. Soc. 1962, 84, 365.
37. T.C. Bruice and T.H. Fife. Hydroxyl Group Catalysis. III. The Nature
of Neighboring Hydroxyl Group Assistance in the Alkaline Hydrolysis
of the Ester Bond. J. Am. Chem. Soc. 1962, 84, 1973.
38. T.C. Bruice and J. J. Bruno. Imidazole Catalysis. IX. The Bell-
shaped pH-Dependence of the Rate of Imidazole Catalysis of d-Thiovalerolactone
Hydrolysis. J. Am. Chem. Soc. 1962, 84, 2128.
40. T.C. Bruice; T.H. Fife; J.J. Bruno and P. Benkovic. Hydroxyl Group
(V) and Imidazole (X) Catalysis. The General Base Catalysis of Ester
Hydrolysis by Imidazole and the Influence of a Neighboring Hydroxyl
Group. J. Am. Chem. Soc. 1962, 84, 3012.
47. T.C. Bruice. Acyl Imidazoles. In Methods in Enzymology; Vol. VI;
Academic Press, 1963; 606.
53. T.C. Bruice and S.J. Benkovic. the Compensation in ? H± and
? S± Accompanying the Conversion of Lower Order Nucleophilic
Displacement Reactions to Higher Order Catalytic Processes. The
Temperature Dependence of the Hydrazinolysis and Imidazole-Catalyzed
Hydrolysis
of Substituted Phenyl Acetates. J. Am. Chem. Soc. 1964, 86, 418.
61. T.C. Bruice and R.G. Willis. The Reaction of Aliphatic Diamines
with Phenyl Acetate. J. Am. Chem. Soc. 1965, 87, 531.
71. L.R. Fedor; T.C. Bruice; K.L. Kirk and J. Meinwald. Aminolysis
of Phenyl Acetates in Aqueous Solutions. V. Hypernucleophilicity Associated
with Constraint of Bond Angles. J. Am. Chem. Soc. 1966, 88, 108.
80. T.C. Bruice; A. Donzel; R.W. Huffman and A.R. Butler. Aminolysis
of Phenyl Acetates in Aqueous Solutions. VII. Observations on the Influence
of Salts, Amine Structure and Base Strength. J. Am. Chem. Soc. 1967,
89, 2106.
82. R.W. Huffman; A. Donzel and T.C. Bruice. Aminolysis of Esters.
VII. The Reaction of Lysine with Phenyl Acetate and Triacetin. J. Org.
Chem. 1967, 32, 1973.
100. S.M. Felton and T.C. Bruice. Mechanism of the Solvolyis of 4-(2'-
Acetoxyphenyl)imidazole. Chem. Commun. (London) 1968, 15, 907-8.
117. T.C. Bruice; A.F. Hegarty; S.M. Felton; A. Donzel and N.G. Kundu.
Aminolysis of Esters. IX. The Nature of the Transition States in the
Aminolysis of Phenyl Acetates. J. Am. Chem. Soc. 1970, 92, 1370.
148. R. Goitein and T.C. Bruice. Effect of Transfer from Water to 1.0
M Water in Dimethyl Sulfoxide on the Reaction of Nucleophiles with
Phenyl Esters. J. Phys. Comm. 1972, 76, 432.
182. T.C. Bruice and I. Oka. Nucleophilic Displacements upon Phenyl
Esters in Which the Direct Relationship between Basicity of the Leaving
Group and Rate Is Determined by Ground State Conformations. A Question
of Concerted Catalysis in the Hydrolysis of Hexachlorophene Esters.
J. Am. Chem. Soc. 1974, 96, 4500.
462. H. Adalsteinsson & T. C. Bruice. What is the Mechanism
of Catalysis of Ester Aminolysis by Weak Amine Bases? Comparison
of
Experimental Studies and Theoretical Investigation of the Aminolysis
of Substituted
Phenyl Esters of Qunoline-6- and -8-Carboxylic Acids. J. Am. Chem.
Soc. 1998, 120, 3440.
Intramolecular Models, efficiency of enzyme catalysis
18. T.C. Bruice and J.M. Sturtevant. An intramolecular model for an
esteratic enzyme. Biochim. Biophys. Acta. 1958, 30, 208-9.
19. T.C. Bruice and J.M. Sturtevant. Imidazole Catalysis. V. The Intramolecular
Participation of the Imidazolyl Group in the Hydrolysis of Some Esters
and the Amide of ?-(4- Imidazolyl)butyric Acid and 4-(2'-Acetoxyethyl)-imidazole.
J. Am. Chem. Soc. 1959, 81, 2860.
22. T.C. Bruice. Imidazole Catalysis. VI. The Intramolecular Nucleophilic
Catalysis of the Hydrolysis of an Acyl Thiol. The Hydrolysis of n-Propyl
?-(4-Imidazolyl)-thiolbutyrate. J. Am. Chem. Soc. 1959, 81, 5444.
23. T.C. Bruice and U.K. Pandit. Intramolecular Models Depicting
the Kinetic Importance of "Fit" in Enzymatic Catalysis.
Proc. Natl. Acad. Sci. 1960, 46, 402.
26. T.C. Bruice and U.K. Pandit. The Effect of Geminal Substitution
Ring Size and Rotamer Distribution on the Intramolecular Nucleophilic
Catalysis of the Hydrolysis of Monophenyl Esters of Dibasic Acids and
the Solvolysis of the Intermediate Anhydrides. J. Am. Chem. Soc. 1960,
82, 5858.
29. T.C. Bruice and T.H. Fife. The Nature of Neighboring Hydroxyl Group
Assistance in the Alkaline Hydrolysis of the Ester Bond. Tetrahedron
Lett. 1961, 8, 263.
41. T.C. Bruice and S.J. Benkovic. A Comparison of the Bimolecular
and Intramolecular Nucleophilic Catalysis of the Hydrolysis of Substituted
Phenyl Acylates by the Dimethylamino Group. J. Am. Chem. Soc. 1963,
85, 1.
42. T.C. Bruice. Intramolecular Catalysis and the Mechanism of Chymotrypsin
Action. Brookhaven Symp. Biol. 1962, 15, 52-84.
68. T.C. Bruice and W.C. Bradbury. The gem Effect. I. The Influence
of 3-Substituents on the Rates of Solvolysis of Glutaric Anhydride.
A Conformational Analysis. J. Am. Chem. Soc. 1965, 87, 4838.
69. T.C. Bruice and W.C. Bradbury. The gem Effect. II. The Influence
of 3-Mono- and 3,3-Disubstitution on the Rates of Solvolysis of Mono-p-bromophenyl
Glutarate. J. Am. Chem. Soc. 1965, 87, 4846.
74. J.W. Thanassi and T.C. Bruice. Neighboring Carboxyl Group Participation
in the Hydrolysis of Monoesters of Phthalic Acid. The Dependence of
Mechanisms on Leaving Group Tendencies. J. Am. Chem. Soc. 1966, 88,
747.
104. T.C. Bruice and S.M. Felton. Intramolecular Amine-Catalyzed Aminolysis
of an Ester. J. Am. Chem. Soc. 1969, 91, 2799.
115. S.M. Felton and T.C. Bruice. Intramolecular General-Base- Catalyzed
Hydrolysis and Aminolysis of the Ester Bond by Imidazole and Quinoline
Bases. J. Am. Chem. Soc. 1969, 91, 6721.
121. T.C. Bruice and A. Turner. Solvation and Approximation. Solvent
Effects on the Bimolecular and Intramolecular Nucleophilic Attack of
Carboxyl Anion on Phenyl Esters. J. Am. Chem. Soc. 1970, 92, 3422.
134. T. Maugh II and T.C. Bruice. The Role of Intramolecular Bifunctional
Catalysis of Ester Hydrolysis in Water. J. Am. Chem. Soc. 1971, 93,
3237.
137. T. Maugh II and T.C. Bruice. Hydrolysis and Aminolysis of O- Acylhydroxyquinolines.
Intracomplex General Base-Catalyzed Aminolysis. J. Am. Chem., Soc.
1971, 93, 6584.
169. G.A. Rogers and T.C. Bruice. Isolation of a Tetrahedral Intermediate
in an Acetyl Transfer Reaction. J. Am. Chem. Soc. 1973, 95, 4452.
183. P.Y. Bruice and T.C. Bruice. Intramolecular General Base Catalyzed
Hydrolysis and Tertiary Amine Nucleophilic Attack vs. General Base
Catalyzed Hydrolysis of Substituted Phenyl Quinoline-8- and -6-carboxylates.
J. Am. Chem. Soc. 1974, 96, 5523.
184. P.Y. Bruice and T.C. Bruice. Aminolysis of Substituted Phenyl
Quinoline-8- and -6-Carboxylates with Primary and Secondary Amines.
Involvement of Proton-Slide Catalysis. J. Am. Chem. Soc. 1974, 96,
5533.
423. F. C. Lightstone; T. C. Bruice. Geminal-Dialkyl Substitution,
Intramolecular Reactions and Enzyme Efficiency. J. Am. Chem. Soc. 1994,
116, 10789.
438. F. C. Lightstone; T. C. Bruice. Ground State Conformations and
Entropic and Enthalpic Factors in the Efficiency of Intramolecular
and Enzymatic Reactions. I Cyclic Anhydride Formation by Substituted
Glutarates, Succinate and 3,6-Endoxod4-tetrahydrophthalate Monophenyl
Esters. J. Am. Chem. Soc. 1996, 118, 2595.
458. F. C. Lightstone & T. C. Bruice. Separation of Ground
State and Transition State Effects in Intramolecular and Enzymatic
Reactions.
II. A Theoretical Study of the Formation of Transition States in
Cyclic Anhydride Formation. J. Am. Chem. Soc. 1997, 119, 9103.
473. F. C. Lightstone & T. C. Bruice. Enthalpy and Entropy
in Ring Closure Reactions. Bioorganic Chem. 1998, 26, 193.
ElcB & Types, Electrostatic
27. T.C. Bruice and T.H. Fife. A Facile Base-catalyzed Ester Hydrolysis
Involving Alkyl-Oxygen Cleavage. The Mechanism of Hydrolysis of Esters
of 4(5)-Hydroxymethylimidazole. J. Am. Chem. Soc. 1961, 83, 1124.
57. T.C. Bruice and J.L. Herz. Hydrolytic Reactions of 4(5)- Hydroxymethylimidazolyl
Acetate, 1-Methyl-5- Hydroxymethylimidazolyl Acetate, 4(5)-Chloromethylimidazole,
and 1-Methyl-5-chloromethylimidazole. J. Am. Chem. Soc. 1964, 86, 4109.
85. T.C. Bruice and B. Holmquist. The Question of the Importance of
Electrostatic Catalysis. I. Comparison of the Reactivity of o- Nitrophenyl
Hydrogen Oxalate and Ethyl O-Nitrophenyl Oxalate toward Nucleophiles.
J. Am. Chem. Soc.1967, 89, 4028.
102. T.C. Bruice and B. Holmquist. The Establishment of a Carbanion
Mechanism for Ester Hydrolysis and the Unimportance of Electrostatic
Effects of a Substituents on the Rates of Hydroxide Ion Attack at the
Ester Carbonyl Group. J. Am. Chem. Soc. 1969, 90, 7136.
105. B. Holmquist and T.C. Bruice. Electrostatic Catalysis. II. A Comparison
of Spontaneous and Alkaline Hydrolytic Rate Constants for a Substituted
O-Nitrophenyl Esters. J. Am. Chem. Soc. 1969, 91, 2982.
106. B. Holmquist and T.C. Bruice. Electrostatic Catalysis. III. Comparison
of the Reactivity of a Substituted O-Nitrophenyl Esters with Anionic
and Amine Nucleophiles. J. Am. Chem. Soc. 1969, 91, 2985.
107. B. Holmquist and T.C. Bruice. The Carbanion (ElcB) Mechanisms
of Ester Hydrolysis. I. Hydrolysis of Malonate Esters. J. Am. Chem.
Soc. 1969, 91, 2993.
108. B. Holmquist and T.C. Bruice. The Carbanion Mechanism of Ester
Hydrolysis. II. o-Nitrophenyl, a-Cyano- and a-Dimethylsulfonioacetate
Esters. J. Am. Chem. Soc. 1969, 91, 3003.
126. R.F. Pratt and T.C. Bruice. The Carbanion Mechanism (ElcB) of
Ester Hydrolysis. III. Some Structure-Reactivity Studies and the Ketene
Intermediate. J. Am. Chem. Soc. 1970, 92, 5956.
257. M. Inoue and T.C. Bruice. The Influence of Electron Delocalization
upon the Rate Constants for Competing BAC2 and Elcb Ester Hydrolyses.
J. Chem. Soc., Chem. Commun. 1981, 17, 884-6.
262. M. Inoue and T.C. Bruice. Extended ElcB Mechanism for Ester Hydrolysis:
Allylic Substitution via Carbanion in Ester Hydrolysis. J. Am. Chem.
Soc. 1982, 104, 1664.
279. M. Inoue and T.C. Bruice. Influence of Steric Effects upon the
Rate Constants for Competing BAC2 and ElcB Ester Hydrolyses. J. Org.
Chem. 1983, 48, 3559.
313. M. Inoue and T.C. Bruice. Mechanistic Change from (ElcB)R to (ElcB)i
Brought about by a Sterically Bulky Substituent in Ester Hydrolysis.
J. Org. Chem. 1986, 51, 959.
The Gem Effect
68. T.C. Bruice and W.C. Bradbury. The gem Effect. I. The Influence
of 3-Substituents on the Rates of Solvolysis of Glutaric Anhydride.
A Conformational Analysis. J. Am. Chem. Soc. 1965, 87, 4838.
69. T.C. Bruice and W.C. Bradbury. The gem Effect. II. The Influence
of 3-Mono- and 3,3-Disubstitution on the Rates of Solvolysis of Mono-p-bromophenyl
Glutarate. J. Am. Chem. Soc. 1965, 87, 4846.
70. T.C. Bruice and W.C. Bradbury. The gem Effect. III. The Influence
of 3-Mono and 3-gem Substitution on the Acid Dissociation Constants
of Glutaric Acid. A Comparison of the Sensitivity of ? pKa of Dicarboxylic
Acids and the Rate of Ring Closure of Their Monoesters to the Intramolecular
Distance Separating Carboxyl Functions. J. Am. Chem. Soc. 1965, 87,
4851.
97. T.C. Bruice and W.C. Bradbury. The gem Effect. IV. Activation Parameters
Accompanying the Increased Steric Requirements of 3,3'-Substituents
in the Solvolysis of Mono-p-bromophenyl Glutarates. J. Am. Chem. Soc.
1968, 90, 3808.
O-acyl Isoureas & Biotin
114. A.F. Hegarty; T.C. Bruice and S.J. Benkovic. Biotin and the Nucleophilicity
of 2-Methoxy-2-imidazoline Toward the sp2 Carbonyl Carbon. Chem. Commun.
1969, 20, 1173-4.
124. T.C. Bruice and A.F. Hegarty. Biotin-Bound CO2 and the Mechanism
of Enzymatic Carboxylation Reactions. Proc. Natl. Acad. Sci. 1970,
65, 805.
128. A.F. Hegarty and T.C. Bruice, Acyl Transfer Reactions from and
to the Ureido Functional Group. I. The Mechanisms of Hydrolysis of
an O-Acylisourea (2-Amino-4,5-benzo-6-oxo-1,3- oxazine). J. Am. Chem.
Soc.1970, 92, 6561.
129. A.F. Hegarty and T.C. Bruice. Acyl Transfer Reactions from and
to the Ureido Functional Group. II. The Mechanisms of Aminolysis of
an O-Acylisourea (2-Amino-4,5-benzo-6-oxo- 1,3-oxazine). J. Am. Chem.
Soc. 1970, 92, 6568.
130. A.F. Hegarty and T.C. Bruice. Acyl Transfer Reactions from
and to the Ureido Functional Group. III. The Mechanism of Intramolecular
Nucleophilic Attack of the Ureido Functional Group upon Acyl Groups.
J. Am. Chem. Soc. 1970, 92, 6575.
135. A.F. Hegarty; R.F. Pratt; T. Guidici and T.C. Bruice. Acyl
Transfer Reactions from and to the Ureido Functional Group. IV.
Neighboring
Carboxyl Group General Acid Catalysis in the Hydrolysis of an
O-Acylisourea (2-Amino-8-carboxy-4-oxo- 3,1,4-benzoxazine). J.
Am. Chem., Soc. 1971,
93, 1428.
141. R.F. Pratt and T.C. Bruice. Reactions of S-Acylisothioureas.
I. S- to N-Acyl Migrations in S-Benzoylisothiobiotin and Analogs.
Biochem.
1971, 10, 3178.
143. T.C. Bruice and R.F. Pratt. An Intramolecular Acyl Transfer
Reaction Limited by Substrate Isomerization. Chem. Commun. 1971,
20, 1259-61.
146. R.F. Pratt and T.C. Bruice. Reactions of S-Acylisothioureas.
II. Effects of Structure and Stereochemistry on the Rates of
Hydrolysis,
Thiol Elimination, and S and N Acyl Migration in Acylic Systems.
J. Am. Chem. Soc. 1972, 94, 2823.
Metal Ion Catalysis
214. M.A. Wells and T.C. Bruice. The Nucleophilicity of Metal
Bound Hydroxide Mechanisms of Displacement on Esters and Transesterification
Involving the Metal-Acyl Anhydride Bond. In Metal-Ligand Interactions
in Organic Chemistry and Biochemistry Part 2; B. Pullman and
N. Goldblum;
Eds.; D. Reidel Publishing Company: Dordrecht-Holland, 1976;
273-284.
206. M.A. Wells; G.A. Rogers and T.C. Bruice. Intramolecular
Hydrolysis of a Methyl Ester by Substrate Bound Metal Hydroxide.
J. Am. Chem.
Soc. 1976, 98, 4336.
218. M.A. Wells and T.C. Bruice. Intramolecular Catalysis of
Ester Hydrolysis by Metal Complexed Hydroxide Ion. Acyl Oxygen
Bond Scission
in Co2+ and Ni2+ Carboxylic Acid Complexes. J. Am. Chem. Soc.
1977, 99, 5341.
Triad
34. T.C. Bruice. The Mechanisms for Chymotrypsin. Proc. Natl.
Acad. Sci. 1961, 47, 1924.
131. T.C. Bruice; P.G. Kury and D.M. McMahon. Chromophoric Lactones
and the Mechanism of Chymotrypsin Action. J. Am. Chem. Soc. 1970,
92, 6674.
150. T.C. Bruice and D.M. McMahon Nucleophilic Selectivity in
Attack at Amide Bonds. Reactivity of Oxygen and Nitrogen Nucleophiles
with
N-Acetyldehydrophenylalanyl-L-proline Diketopiperazine. Biochem.
1972, 11, 1273.
169. G.A. Rogers and T.C. Bruice. Isolation of a Tetrahedral
Intermediate in an Acetyl Transfer Reaction. J. Am. Chem. Soc.
1973, 95, 4452.
177. G.A. Rogers and T.C. Bruice. Control of Modes of Intramolecular
Imidazole Catalysis of Ester Hydrolysis by Steric and Electronic
Effects. J. Am. Chem. Soc. 1974, 96, 2463.
178. G.A. Rogers and T.C. Bruice. Synthesis and Evaluation of
a Model for the So-Called "Charge-Relay" System of
the Serine Esterases. J. Am. Chem. Soc. 1974, 96, 2473.
179. G.A. Rogers and T.C. Bruice. The Mechanisms of Acyl Group
Transfer from a Tetrahedral Intermediate. J. Am. Chem. Soc. 1974,
96, 2481.
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