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
2021
Pyun, S.Y. | Paik, K.C. | Han, M.S. | Cho, B.R.
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 Brönsted 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.
Show more [+] Less [-]Bibliographic information
This bibliographic record has been provided by Korea Agricultural Science Digital Library