33963-55-2Relevant academic research and scientific papers
Substituent effects on the base-catalysed hydrolysis of phenyl esters of ortho-substituted benzoic acids
Bauerova, Ingrid,Ludwig, Miroslav
, p. 770 - 784 (2007/10/03)
Fourteen model phenyl esters of 2-substituted benzoic acids were synthesised. Structures and purity of model compounds were confirmed by 1H and 13C NMR spectroscopy, as well as by HPLC and elemental analysis. Kinetics of base-catalysed hydrolysis of model phenyl esters occurring by the BAC2 mechanism were measured by UV spectrophotometry in 50% (v/v) aqueous dimethyl sulfoxide solutions at 25 °C under pseudo-first-order reaction conditions (c(NaOH) = 0.001-1.0 mol 1-1). Linear relation between JE- and log kobs with the slope close to unity was found for all model compounds. Neither one-parameter nor multiparameter Hammett-type description of variability of experimental data obtained for phenyl esters of 2-substituted benzoic acids was found. Two groups (conjugating and non-conjugating) were created by division of ortho-substituents in ortho-position using the AISE theory, based on their interaction with the reaction centre.
Separation of Polar and Steric Effects: Reactions of ortho-Substituted Benzoate and 3-Substituted 2-Naphthoate Ions with Picryl Bromide
Ananthakrishnanadar, P.
, p. 343 - 346 (2007/10/02)
Rate constants for the reactions of ortho-substituted benzoate and 3-substituted 2-naphthoate ions with picryl bromide have been determined at 30 deg C, 40 deg C and 50 +/- 0.1 deg C in 80percent methanol-20percent water (v/v) mixtures.Electron-donating groups increase the rate, while electron-withdrawing groups decrease the rate.The rate data are analysed through multiple correlations involving electronic and steric terms associated with substituents.The steric term is rate-accelerating.
