Mechanistic change in the reactivity of substituted phenyl acetates over phenyl thiolacetates toward imidazole in aqueous phase was written by Rajarathnam, D.;Jeyakumar, T.;Nadar, P. Ananthakrishna. And the article was included in International Journal of Chemical Kinetics in 2005.SDS of cas: 35065-86-2 This article mentions the following:
The kinetics of aminolysis of several substituted Ph 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 (λmax = 272-401 nm), under excess free imidazole, pseudo-first-order rate constants (kobs) are obtained. For the esters with good nucleofuges, the reaction follows clean second-order kinetics and the plots of (kobs – kH) against free imidazole concentration are linear at constant pH. The macroscopic nucleophilic substitution rate constants (kN) are obtained as the slopes of these plots and are 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 k’2 on free imidazole is observed Accordingly, the microscopic rate constants for the assisted paths viz. kga and kgb were disseminated besides for simple bimol. 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 analog thiolesters under identical reaction conditions showed remarkable mechanistic differences which are discussed. 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 experiment, the researchers used many compounds, for example, 3-Bromophenyl acetate (cas: 35065-86-2SDS of cas: 35065-86-2).
3-Bromophenyl acetate (cas: 35065-86-2) belongs to organobromine compounds. Bromo compounds are employed in a variety of metal-catalyzed coupling reactions. They are also ideal candidates for the synthesis of Grignard reagents that have wide-applicability in organic synthesis. alpha-Bromoesters are employed in the Reformatsky reaction for the synthesis of beta-hydroxyesters. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.SDS of cas: 35065-86-2
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary