- Kinetic study on aminolysis of aryl X-substituted-cinnamates in acetonitrile: Differential medium effect determines reactivity and reaction mechanism
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A kinetic study on nucleophilic substitution reactions of 2,4-dinitrophenyl X-substituted-cinnamates (1a-1f) and Y-substituted-phenyl cinnamates (2a-2g) with a series of alicyclic secondary amines in MeCN at 25.0 ± 0.1 °C is reported. The Br?nsted-type pl
- Um, Ik-Hwan,Bae, Ae-Ri,Dust, Julian M.
-
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- Kinetic study on alkaline hydrolysis of Y-substituted phenyl X-substituted benzenesulfonates: Effects of changing nucleophile from azide to hydroxide ion on reactivity and transition-state structure
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Second-order rate constants (kOH-) for alkaline hydrolysis of 2,4-dinitrophenyl X-substituted benzenesulfonates (1a-1f) and Y-substituted phenyl 4-nitrobezenesulfonates (2a-2g) have been measured spectrophotometrically. Comparison of kOH/
- Moon, Ji-Hyun,Kim, Min-Young,Han, So-Yeop,Um, Ik-Hwan
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p. 1563 - 1568
(2015/08/11)
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- Kinetic study on alkaline hydrolysis of Y-substituted phenyl picolinates: Effects of modification of nonleaving group from benzoyl to picolinyl on reactivity and reaction mechanism
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Second-order rate constants (kOH-) for alkaline hydrolysis of Y-substituted phenyl picolinates (6a-6i) have been measured spectrophotometrically. A linear Bronsted-type plot is obtained with βlg = -0.34, which is typical for reactions reported previously to proceed through a stepwise mechanism with formation of an addition intermediate being the rate-determining step (RDS). However, σYo constants result in a much poorer Hammett correlation than σY- constants. Furthermore, the Yukawa-Tsuno plot exhibits an excellent linear correlation with ρY = 0.82 and r = 0.72, indicating that a negative charge develops partially on the O atom of the leaving group in the RDS. Thus, the reactions have been concluded to proceed through a forced concerted mechanism with a highly unstable intermediate 7. Comparison of the current kinetic data with those reported previously for the corresponding reactions of Y-substituted phenyl benzoates has revealed that modification of the nonleaving group from benzoyl to picolinyl causes not only an increase in reactivity but also a change in the reaction mechanism (i.e., from a stepwise mechanism to a forced concerted pathway).
- Kim, Myung-Joo,Kim, Min-Young,Um, Ik-Hwan
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p. 1138 - 1142
(2015/07/15)
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- Study on the transesterification of methyl aryl phosphorothioates in methanol promoted by Cd(II), Mn(II), and a synthetic Pd(II) complex
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Methanol solutions containing Cd(II), Mn(II), and a palladacycle, (dimethanol bis(N,N-dimethylbenzylamine-2C,N)palladium(II) (3), are shown to promote the methanolytic transesterification of O-methyl O-4-nitrophenyl phosphorothioate (2b) at 25 °C with impressive rate accelerations of 10 6-1011 over the background methoxide promoted reaction. A detailed mechanistic investigation of the methanolytic cleavage of 2a-d having various leaving group aryl substitutions, and particularly the 4-nitrophenyl derivative (2b), catalyzed by Pd-complex 3 is presented. Plots of k obs versus palladacycle [3] demonstrate strong saturation binding to form 2b:3. Numerical fits of the kinetic data to a universal binding equation provide binding constants, Kb, and first order catalytic rate constants for the methanolysis reaction of the 2b:3 complex (kcat) which, when corrected for buffer effects, give corrected (kcat corr) rate constants. A sigmoidal shaped plot of log(k catcorr) versus sspH (in methanol) for the cleavage of 2b displays a broad sspH independent region from 5.6 ≥ sspH ≥ ~10 with a k minimum = (1.45 ± 0.24) × 10-2 s-1 and a [lyoxide] dependent wing plateauing above a kinetically determined sspKa of 12.71 ± 0.17 to give a k maximum = 7.1 ± 1.7 s-1. Bronsted plots were constructed for reaction of 2a-d at sspH 8.7 and 14.1, corresponding to reaction in the midpoints of the low and high s spH plateaus. The Bronsted coefficients (βLG) are computed as -0.01 ± 0.03 and -0.86 ± 0.004 at low and high sspH, respectively. In the low sspH plateau, and under conditions of saturating 3, a solvent deuterium kinetic isotope effect of kH/kD = 1.17 ± 0.08 is observed; activation parameters (ΔHPd? = 14.0 ± 0.6 kcal/mol and ΔSPd?= -20 ± 2 cal/mol?K) were obtained for the 3-catalyzed cleavage reaction of 2b. Possible mechanisms are discussed for the reactions catalyzed by 3 at low and high sspH. This catalytic system is shown to promote the methanolytic cleavage of O,O-dimethyl phosphorothioate in CD3OD, producing (CD3O)2P=O(S-) with a half time for reaction of 34 min.
- Edwards, David R.,Neverov, Alexei A.,Brown, R. Stan
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scheme or table
p. 1786 - 1797
(2011/04/23)
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- Structure and mechanism of PhnP, a phosphodiesterase of the carbon-phosphorus lyase pathway
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PhnP is a phosphodiesterase that plays an important role within the bacterial carbon-phosphorus lyase (CP-lyase) pathway by recycling a "dead-end" intermediate, 5-phospho-α-d-ribosyl 1,2-cyclic phosphate, that is formed during organophosphonate catabolism
- He, Shu-Mei,Wathier, Matthew,Podzelinska, Kateryna,Wong, Matthew,McSorley, Fern R.,Asfaw, Alemayehu,Hove-Jensen, Bjarne,Jia, Zongchao,Zechel, David L.
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experimental part
p. 8603 - 8615
(2012/07/27)
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- Pitfalls in assessing the α-effect: Reactions of substituted phenyl methanesulfonates with HOO-, OH-, and substituted phenoxides in H2O
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Toward resolving the current controversy regarding the validity of the α-effect, we have examined the reactions of Y-substituted phenyl methanesulfonates 1a-1l with HOO-, OH-, and Z-substituted phenoxides in the gas phase versus solu
- Um, Ik-Hwan,Im, Li-Ra,Buncel, Erwin
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supporting information; experimental part
p. 8571 - 8577
(2011/03/20)
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- Analysis of linear free-energy relationships combined with activation parameters assigns a concerted mechanism to alkaline hydrolysis of X-substituted phenyl diphenylphosphinates
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A kinetic study is reported for alkaline hydrolysis of X-substituted phenyl diphenylphosphinates (1a-i). The Bronsted-type plot for the reactions of 1a-i is linear over 4.5 pKa units with βlg= -0.49, a typical βlg value for reactions which proceed through a concerted mechanism. The Hammett plots correlated with σo and σ- constants are linear but exhibit many scattered points, while the corresponding Yukawa-Tsuno plot results in excellent linear correlation with ρ= 1.42 and r=0.35. The r value of 0.35 implies that leaving-group departure is partially advanced at the rate-determining step (RDS). A stepwise mechanism, in which departure of the leaving group from an addition intermediate occurs in the RDS, is excluded since the incoming HO - ion is much more basic and a poorer nucleofuge than the leaving aryloxide. A dissociative (DN + AN) mechanism is also ruled out on the basis of the small βlg value. As the substituent X in the leaving group changes from H to 4-NO2 and 3,4-(NO2)2, ΔH≠ decreases from 11.3 kcal mol-1 to 9.7 and 8.7 kcal mol-1, respectively, while ΔS≠ varies from -22.6 cal mol-1 K-1 to -21.4 and -20.2 cal mol-1 K-1, respectively. Analysis of LFERs combined with the activation parameters assigns a concerted mechanism to the current alkaline hydrolysis of 1a-i.
- Um, Ik-Hwan,Han, Jeong-Yoon,Hwang, So-Jeong
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supporting information; experimental part
p. 7324 - 7330
(2009/08/07)
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- Aminolyses of aryl diphenylphosphinates and diphenylphosphinothioates: Effect of modification of electrophilic center from P=O to P=S
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(Chemical Equation Presented) A kinetic study is reported for aminolysis of aryl diphenylphosphinothioates (2a-i). The phosphinothioates 2a-i are less reactive than aryl diphenylphosphinates (1a-i), the oxygen analogues of 2a-i, regardless of the basicity
- Um, Ik-Hwan,Akhtar, Kalsoom,Shin, Young-Hee,Han, Jeong-Yoon
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p. 3823 - 3829
(2008/02/02)
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- Alkaline phosphatase mono- and diesterase reactions: Comparative transition state analysis
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Enzyme-catalyzed phosphoryl transfer reactions have frequently been suggested to proceed through transition states that are altered from their solution counterparts. Previous work with Escherichia coli alkaline phosphatase (AP), however, suggests that thi
- Zalatan, Jesse G.,Herschlag, Daniel
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p. 1293 - 1303
(2007/10/03)
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- Mechanistic change in the reactivity of substituted phenyl acetates over phenyl thiolacetates toward imidazole in aqueous phase
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The kinetics of aminolysis of several substituted phenyl acetates by imidazole is studied in aqueous medium at 20°C and an ionic strength of 0.1 M (KCl). By following the leaving groups spectrophotometrically (λ max = 272-401 nm), under excess free imidazole, pseudo-first-order rate constants (κobs) are obtained. For the esters with good nucleofuges, the reaction follows clean second-order kinetics and the plots of (κobs - κH) against free imidazole concentration are linear at constant pH. The macroscopic nucleophilic substitution rate constants (κN) are obtained as the slopes of these plots and found to be pH independent. For the esters with poor nucleofuges, a rate dependence on more than first power of the free imidazole and a linear dependence of κ′2 on free imidazole is observed. Accordingly, the microscopic rate constants for the assisted paths viz. κga and κgb have been disseminated besides for simple bimolecular attack. The Broensted-type plots and Hammett plots were constructed whose slope values are consistent with a stepwise mechanism through a bipolar tetrahedral addition intermediate whose formation or breakdown being rate determining for various paths. Comparison of this reaction of oxyesters with the earlier reported works on similar reaction of analogue thiolesters under identical reaction conditions showed remarkable mechanistic differences which are discussed in detail. The discussion is extended to include the details on previously studied ammonolysis of these two types of esters wherein thiolesters showed differed reactivity than that reported in the present study.
- Rajarathnam,Jeyakumar,Nadar, P. Ananthakrishna
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p. 211 - 221
(2007/10/03)
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- Kinetics and mechanistic study of the reaction of cyclic anhydrides with substituted phenols. Structure-reactivity relationships
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(Chemical Equation Presented) The kinetic of the reactions of phthalic and maleic anhydrides with different substituted phenols (Z-PhOH with Z = H, m-CH3, p-CH3, m-Cl, p-Cl, and m-CN) were studied in aqueous solution. Two kinetic processes well separated in time were observed. The fast one is attributed to the formation of the aryl ester in equilibrium with the anhydride and allows the determination of the rate of nucleophilic attack of the phenol on the anhydride (k-A). From the slow kinetic process, the equilibrium constant for this reaction was determined. The Broensted-type plots for the nucleophilic attack of substituted phenols on the anhydrides were linear with slopes βNuc of 0.45 and 0.56 for phthalic and maleic anhydride, respectively. The results are consistent with a mechanism involving rate-determining nucleophilic attack and also with a concerted mechanism. The calculated effective charge on the atoms involved in the reactions and the Broensted β values are consistent with a mechanism involving a concerted or enforced concerted mechanism where a tetrahedral intermediate with significant lifetime is not formed along the reaction coordinate. The latter mechanism is preferred over the stepwise process.
- Andres, Gabriel O.,De Rossi, Rita H.
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p. 1445 - 1449
(2007/10/03)
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- Transition-state variation in the nucleophilic substitution reactions of aryl bis(4-methoxyphenyl) phosphates with pyridines in acetonitrile
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The kinetics and mechanism of the reactions of Z-aryl bis(4-methoxyphenyl) phosphates, (4-MeOC6H4O)2P(=O) OC6H4Z, with pyridines (XC5H4N) are investigated in acetonitrile at 55.0 °C. In the case of more basic phenolate leaving groups (Z = 4-Cl, 3-CN), the magnitudes of βx (βnuc) and βz (βlg) indicate that mechanism changes from a concerted process (βx = 0.22-0.36, βz = -0.42 to -0.56) for the weakly basic pyridines (X = 3-Cl, 4-CN) to a stepwise process with rate-limiting formation of a trigonal bipyramidal pentacoordinate (TBP-5C) intermediate (βx = 0.09-0.14, βz = -0.08 to -0.28) for the more basic pyridines (X = 4-NH2, 3-CH3). This proposal is supported by a large negative cross-interaction constant (ρxz = -1.98) for the former and a positive ρxz(+0.97) for the latter processes. In the case of less basic phenolate leaving groups (Z = 3-CN, 4-NO2), the unusually small magnitude of βz values is indicative of a direct backside attack TBP-5C TS in which the two apical sites are occupied by the nucleophile and leaving group, ap(NX)-ap(LZ). The instability of the putative TBP-5C intermediate leading to a concerted displacement is considered to result from relatively strong proximate charge transfer interactions between the π-lone pairs on the directly bonded equatorial oxygen atoms and the apical bond (no(eq) - ?*(ap)). These are supported by the results of natural bond orbital (NBO) analyses at the NBO-HF/6-311+G**//B3LYP/6-311+G** level of theory.
- Lee, Hai Whang,Guha, Arun Kanti,Kim, Chang Kon,Lee, Ikchoon
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p. 2215 - 2222
(2007/10/03)
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- Reinterpretation of curved hammett plots in reaction of nucleophiles with aryl benzoates: Change in rate-determining step or mechanism versus ground-state stabilization
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A kinetic study is reported for the reaction of the anionic nucleophiles OH-, CN-, and N3- with aryl benzoates containing substituents on the benzoyl as well as the aryloxy moiety, in 80 mol % H2O-20 mol % dimethyl sulfoxide at 25.0 °C. Hammett log k vs σ plots for these systems are consistently nonlinear. However, a possible traditional explanation in terms of a mechanism involving a tetrahedral intermediate with curvature resulting from a change in rate-determining step is considered but rejected. The proposed explanation involves ground-state stabilization through resonance interaction between the benzoyl substituent and the electrophilic carbonyl center in the two-stage mechanism. Accordingly, the data are nicely accommodated on the basis of the Yukawa-Tsuno equation, which gives linear plots for all three nuceophiles. Literature reports of the mechanism of acyl transfer processes are reconsidered in this light.
- Um, Ik-Hwan,Han, Hyun-Joo,Ahn, Jung-Ae,Kang, Swan,Buncel, Erwin
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p. 8475 - 8480
(2007/10/03)
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- The mechanism of the metal ion promoted cleavage of RNa phosphodiester bonds involves a general acid catalysis by the metal aquo ion on the departure of the leaving group
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A series of uridine 3′-alkyl phosphates and 3′-aryl phosphates were synthesised and their cleavage was studied in the presence of Zn2+ aquo ions. A βlg value was determined for the Zn2+ promoted cleavage of both types of compounds. Comparison of the results obtained to those reported previously for the cleavage of the same substrates in the absence of metal ion catalysts suggests that the alkyl leaving group departs as an alcohol in the presence of metal ion catalysts. Furthermore, metal ion catalysts seem to enhance the departure. The aryl leaving group, in contrast, departs as an oxyanion.
- Mikkola, Satu,Stenman, Eeva,Nurmi, Kirsi,Yousefi-Salakdeh, Esmail,Stroemberg, Roger,Loennberg, Harri
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p. 1619 - 1625
(2007/10/03)
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- Acid dissociation constants of phenols and reaction mechanism for the reactions of substituted phenyl benzoates with phenoxide anions in absolute ethanol
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Acid dissociation constants of 10 substituted phenols have been measured by a kinetic method together with second-order rate constants for the reactions of aryl benzoates (X-C6H4CO-OC6H4-Y) with Z-substituted phenoxide (Z-C6H4O-) and EtO- in absolute ethanol at 25.0 ± 0.1°C. The kinetic results support a stepwise mechanism for the present acyl-transfer reaction.
- Um, Ik-Hwan,Hong, Yeon-Ju,Kwon, Dong-Sook
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p. 5073 - 5082
(2007/10/03)
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- Highly Sterically hindered Carbon Acids: The Intrinsic Reactivity of 5,5',5''-Trimethyl- and 3,3',3'',5,5',5''-Hexamethyl-2,2',2'',4,4',4''-Hexanitrotriphenylmethanes
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Rate constants (kpB,kpBH) for the reversible deprotonation of 5,5',5''-trimethyl- and 3,3',3'',5,5',5''-hexamethyl-2,2',2'',4,4',4''-hexanitrotriphenylmethanes (2 and 3) by primary aliphatic amines, piperidine and morpholine as well as by phenoxide anions and hydroxide anion have been measured in H2O-Me2SO (20:80) at 25 deg C.Comparison of the results obtained with those for 2,2',2'',4,4',4''-hexanitrotriphenylmethane (1a) shows that the introduction of methyl groups in positions adjacent to the nitro groups decreases markedly the thermodynamic acidity of theexocyclic CH group: ΔpK2a1a = 1.68; ΔpK3a1a = 6.48.It is suggested that these decreases are very likely the reflection of a twisting of the nitro groups out of their attached aromatic planes and therefore of a reduced resonance stabilization of the conjugated carbanions C-2 and C-3.Other important steric effects are operating in the ionization of 2 and 3.These arise from the accumulation of ortho-nitro groups in the triphenylmethane system which makes the approach of the base reagents from the exocyclic carbon of 2 and 3 very difficult.The finding of extremely low intrinsic reactivities for 2 and 3 and the observation of a much greater catalytic efficiency of primary amines than of secondary amines in assisting the proton transfers are the two most striking manifestations of these F-strain effects.
- Terrier, Francois,Xiao, Lan,Farrell, Patrick G.,Moskowitz, Danielle
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p. 1259 - 1263
(2007/10/02)
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- Heterolysis and homolysis energies for some carbon-oxygen bonds
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Methods described previously for obtaining heterolysis (ΔHhet) and homolysis (ΔHhomo) enthalpies for bonds that can be cleaved to produce resonance-stabilized carbenium ions, anions, and radicals are extended to the study of carbon-oxygen bonds through the reactions of resonance-stabilized carbenium ions with substituted phenoxide ions. Titration calorimetry was used to obtain the heat of heterolysis, and the second-harmonic ac voltammetry (SHACV) method was used to obtain reversible oxidation potentials for the anions. In several cases, the electrode reactions were so fast that reversible potentials were obtained only with the greatest difficulty. Nonetheless, there is remarkably good agreement between these oxidation potentials for phenoxide ions obtained by electrochemical methods in sulfolane solution and those reported by others using entirely different techniques in different media. Such agreement provides unprecedented evidence for the soundness of the various methods used to study redox potentials of organic ions and radicals. As before, a wide variety of correlations was tested between ΔHhet and ΔHhomo. These two properties showed little correlation with each other, but ΔHhet gave good correlations between many properties for which neutral species are converted into ions or vice versa, such as redox potentials of both types of ions, the pKas of the anions, or the free energies of electron transfer. In contrast to the earlier study of cleavage to carbanions and carbenium ions, the present ΔHhet values are predicted well by a general equation that employs the pKR+ of the carbenium ion (without modification) and the pKa of the phenol. The improvement is consistent with the fact that the cleavage of carbon-oxygen bonds of the triarylcarbinols used to establish the pKR+ stability scale is a more appropriate model for the heterolysis of carbon-oxygen bonds in sulfolane at 25°C than it is for the cleavage of carbon-carbon bonds under the same conditions.
- Arnett, Edward M.,Amarnath, Kalyani,Harvey, Noel G.,Venimadhavan, Sampath
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p. 7346 - 7353
(2007/10/02)
-
- A comprehensive view of the gas-phase reaction of fluoride ions and acetic acid derivatives
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The gas-phase reaction of F- with several acetic acid derivatives (MeCOX) is shown to proceed primarily by proton abstraction in the collision complex, rather than nucleophilic displacement, leading to the facile formation of FHX- or CH2CFO-.
- Riveros, Jose M.
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p. 773 - 774
(2007/10/02)
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- A systematic entropy relationship for the general-base catalysis of the deprotonation of a carbon acid. A quantitative probe of transition-state solvation
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The general-base-catalyzed deprotonation of a carbon acid, the l-methyl-4-(phenylacetyl)pyridinium cation (pKa = 9.02 at 25 °C), has been investigated for 32 general-base catalysts (25 amines and seven phenoxide ions) in aqueous solution. Amines give a generally scattered Bronsted plot; ring-substituted benzylamines have ?= 0.52, and ring-substituted phenoxides have ?= 0.60, with the phenoxides being more reactive than amines of similar basicity. The temperature dependences of the general-base-catalyzed deprotonation of this carbon acid have been measured over the range 15-45 °C for 12 base catalysts (eight primary, secondary, and tertiary amines; 4-(dimethylamino)pyridine; two phenoxide ions; hydroxide ion). The entropies of activation for these deprotonations show a clean curvilinear dependence upon the entropies of protonation of these base species, with the hydroxide ion being the only significant deviant from this relationship. This observation quantitatively establishes the importance of solvation effects as the major source of deviations that are commonly observed in Bronsted relationships for general-base-catalyzed processes.
- Bunting, John W.,Stefanidis, Dimitrios
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p. 779 - 786
(2007/10/02)
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- Effective Charge Development in Ester Hydrolysis Catalyzed by Cationic Micelles
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Reaction of hydroxide ion with substituted phenyl laurates is catalyzed by micelles containing CTAB (cetyltrimethylammonium bromide).The observed rate constants for ester consumption obey a Michaelis-Menten-like rate law, kobsd = (kOHKeq + kOHcat)/(Keq + ), where kOHcat is the second order rate constant for reaction of hydroxide ion with micelle-bound ester, Keq is a partition coefficient for dissociation of ester from the micelle-bound ester, and kOH is the second order rate constant for reaction of free ester with hydroxide ion.The value of the parameter Keq is independent of the nature of the substituent on the ester.The ratio kOHcat/Keq represents the free energy change from ester in aqueous solution to the transition state of the ester reaction in the micellar pseudophase.The dependence of log kOHcat/Keq on the pKa of the leaving phenol obeys a linear Bronsted equation with β1g = -0.51, and log kOH obeys a linear Bronsted equation with β1g = -0.56.Since both Bronsted parameters refer to catalyzed and uncatalyzed reactions starting from the same standard state (aqueous solution), the effective charge in the transtition state of both reactions is almost the same.The microscopic medium is thus similar for both cases, consistent with the COOAr moiety's residing in an aqueous-like region of the pseudophase in the catalytic process.
- Al-Awadi, Nouria,Williams, Andrew
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p. 2001 - 2004
(2007/10/02)
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- The one-electron reduction potential of 4-substituted phenoxyl radicals in water
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By means of pulse radiolysis the one-electron reduction potentials of twelve 4-substituted phenoxy radicals have been determined. The main reference used was the ClO2./ClO2- couple. By combining the redox potentials of phenoxyl radicals with the aqueous acidities of phenols the bond strength of the phenolic O-H bond was calculated. These values were found to be in good agreement with O-H bond dissociation enthalpies measured in the gas phase.
- Lind,Shen,Eriksen,Merényi
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p. 479 - 482
(2007/10/02)
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- ENHANCED REACTIVITY OF AN α-NUCLEOPHILE IN WATER-DIMETHYL SULFOXIDE MIXTURES. A TRANSITION STATE EFFECT.
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The reactivity of the anion of α,α,α-trifluoroacetophenone oxime towards p-nitrophenylacetate is considerably enhanced relative to that of the similarly basic p-chlorophenoxide anion on addition of Me2SO to aqueous solutions.This is shown to be due to an
- Laloi-Diard, Marguerite,Verchere, Jean-Francois,Gosselin, Patrick,Terrier, Francois
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p. 1267 - 1268
(2007/10/02)
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- Nucleophilic Catalysis of the Hydrolysis of Phenyl Acetates by the Succinimide Anion in Aqueous Solution
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Kinetic studies were conducted on the disapperance of some phenyl acetates in aqueous solutions buffered by succinimide/succinimide anion at 30 deg C.The most reasonable mechanistic scheme, compatible with the data, is that shown in Scheme I involving nuc
- Huffman, Robert W.
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p. 3687 - 3691
(2007/10/02)
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- A Mechanistic Change in the Alkaline Hydrolysis of Esters of Fluorene-9-carboxylic Acid
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The Broensted leaving group (βlg) plot for the alkaline hydrolysis of fluorene-9-carboxylate esters in the pH region corresponding to the existence of the ester anion shows a minimum flanked by a region of high negative βlg (-1.01), corresponding to an E1cb pathway and, for esters of pKlg >9.5, a region of positive βlg (+0.11).
- Alborz, Manoochehr,Douglas, Kenneth T.
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p. 728 - 729
(2007/10/02)
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