Kinetics of the reaction of 4-nitrophenyl benzoates with 4-chlorophenol in the presence of potassium carbonate in dimethylformamide
- 1 June 2006
- journal article
- Published by Pleiades Publishing Ltd in Russian Journal of Organic Chemistry
- Vol. 42 (6) , 865-872
- https://doi.org/10.1134/s1070428006060091
Abstract
The effect of the substituent in the benzoyl group on the relative rate and activation parameters of transesterification of substituted 4-nitrophenyl benzoates with 4-chlorophenol in dimethylformamide in the presence of potassium carbonate was studied by the competing reaction technique. The whole series of benzoates showed the enthalpy-entropy compensation effect. 4-Nitrophenyl benzoates having electronacceptor substituents give rise to isokinetic relationship with an isokinetic temperature β of 382 K. The mechanism of the transesterification process is discussed.Keywords
This publication has 27 references indexed in Scilit:
- Concerted Organic and Bio-organic MechanismsPublished by Taylor & Francis ,2020
- Curved Hammett Plot in Alkaline Hydrolysis of O-Aryl Thionobenzoates: Change in Rate-Determining Step versus Ground-State StabilizationThe Journal of Organic Chemistry, 2004
- Serine carboxypeptidase-like acyltransferasesPhytochemistry, 2004
- Relationship between nucleophilicity/electrophilicity indices and reaction mechanisms for the nucleophilic substitution reactions of carbonyl compoundsJournal of Physical Organic Chemistry, 2004
- Design of Novel Antibiotics that Bind to the Ribosomal Acyltransfer SiteJournal of the American Chemical Society, 2002
- Evidence of a stepwise acyl-transfer reaction mechanism: Nonlinear Hammett plots for reactions of p-nitrophenyl substituted benzoates with hydroxide and p-chlorophenoxideTetrahedron Letters, 1997
- Acid dissociation constants of phenols and reaction mechanism for the reactions of substituted phenyl benzoates with phenoxide anions in absolute ethanolTetrahedron, 1997
- Concerted or Stepwise Mechanisms for Acyl Transfer Reactions of p-Nitrophenyl Acetate? Transition State Structures from Isotope EffectsJournal of the American Chemical Society, 1994
- Structure-reactivity correlations for reactions of substituted phenolate anions with acetate and formate estersJournal of the American Chemical Society, 1993
- A single transition state in the reaction of aryl diphenylphosphinate esters with phenolate ions in aqueous solutionJournal of the American Chemical Society, 1988