26163-41-7Relevant academic research and scientific papers
Reactions of 4-Nitrophenyl 5-substituted Furan-2-carboxylates with R2NH/R2NH2+ in 20 mol% DMSO(aq): Effect of Aryl Group on the Acyl-Transfer Reaction
Pyun, Sang Yong,Paik, Kyu Cheol,Han, Man So,Cho, Bong Rae
supporting information, p. 994 - 1000 (2021/05/11)
Reactions of 4-nitrophenyl 2-furoates (1a–e) with R2NH/R2NH2+ in 20 mol% DMSO(aq) have been studied. The reactions produced aminolysis products and exhibited second-order kinetics. The Br?nsted plots were linear with βnuc values of 0.75–0.89, which remained nearly the same for all 5-furyl substituents. The rate data showed excellent correlations on the Yukawa-Tsuno plots with ρ(x)?=?0.72–1.1, and r?=?0.55–0.95, respectively. The ρ value increased and r value decreased with a stronger nucleophile, indicating an increase in the electron density at the C-O bond and a decrease in the resonance contribution. The results have been interpreted with the addition–elimination mechanism in which the second step is the rds. By comparing with the data for ArC(O)OC6H4-4-NO2 (Ar?=?Ph, thienyl), the effect of the aryl group on the acyl transfer reaction was assessed.
