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Choice of solvent (MeCN vs H(2)O) decides rate-limiting step in S(N)Ar aminolysis of 1-fluoro-2,4-dinitrobenzene with secondary amines: importance of Brønsted-type analysis in acetonitrile.
A kinetic study is reported for nucleophilic substitution reactions of 2,4-dinitro-1-fluorobenzene (DNFB) with a series of secondary amines in MeCN and H2O at 25.0 degrees C. The reaction in MeCNExpand
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The α-effect and its modulation by solvent
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Effects of amine nature and nonleaving group substituents on rate and mechanism in aminolyses of 2,4-dinitrophenyl X-substituted benzoates.
Second-order rate constants have been measured for the reactions of 2,4-dinitrophenyl X-substituted benzoates (1a-f) with a series of primary amines in 80 mol % H(2)O/20 mol % DMSO at 25.0 +/- 0.1Expand
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Mechanistic assessment of S(N)Ar displacement of halides from 1-halo-2,4-dinitrobenzenes by selected primary and secondary amines: Brønsted and Mayr analyses.
Pseudo-first-order rate constants (k(obsd)) have been measured spectrophotometrically for nucleophilic substitution reactions of 1-X-2,4-dinitrobenzenes (1a-d, X = F, Cl, Br, I) with various primaryExpand
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Alkali metal ion catalysis and inhibition in nucleophilic displacement reactions at phosphorus centers: ethyl and methyl paraoxon and ethyl and methyl parathion.
We report on the ethanolysis of the P=O and P=S compounds ethyl and methyl paraoxon (1a and 1b) and ethyl and methyl parathion (2a and 2b). Plots of spectrophotometrically measured rate constants,Expand
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Aminolysis of Y-substituted-phenyl 2-methoxybenzoates in acetonitrile: effect of the o-methoxy group on reactivity and reaction mechanism.
  • I. Um, Ae Ri Bae
  • Chemistry, Medicine
  • The Journal of organic chemistry
  • 12 August 2011
Second-order rate constants (k(N)) were measured for aminolyses of Y-substituted-phenyl 2-methoxybenzoates 2a-i and 4-nitrophenyl X-substituted-benzoates 3a-j in MeCN at 25.0 °C. The Brønsted-typeExpand
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Effect of amine nature on reaction rate and mechanism in nucleophilic substitution reactions of 2,4-dinitrophenyl X-substituted benzenesulfonates with alicyclic secondary amines.
Second-order rate constants have been measured for reactions of 2,4-dinitrophenyl X-substituted benzenesulfonates with a series of alicyclic secondary amines. The reaction proceeds through S-O andExpand
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Aminolyses of aryl diphenylphosphinates and diphenylphosphinothioates: effect of modification of electrophilic center from P=O to P=S.
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,Expand
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Aminolysis of Y-substituted phenyl diphenylphosphinates and benzoates: effect of modification of electrophilic center from C=O to P=O.
The effect of modification of the electrophilic center from C=O to P=O on reactivity and reaction mechanism has been investigated for aminolysis of Y-substituted phenyl diphenylphosphinates (1a-j)Expand
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Aminolysis of X-substituted phenyl diphenylphosphinates: effect of amine nature on reactivity and transition-state structure.
A kinetic study is reported for aminolysis of X-substituted phenyl diphenylphosphinates (1a-i) in 80 mol % H(2)O/20 mol % dimethyl sulfoxide at 25.0 +/- 0.1 degrees C. The Brønsted-type plot for theExpand
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