Fig. 5: Chloride-induced activation of a responsive foldamer.
From: Switching imidazole reactivity by dynamic control of tautomer state in an allosteric foldamer
The reaction of bis(4-nitrophenylcarbonate) 4 with (a) imidazole (R = H) to give adduct 5; benchmark compound 2 to give adduct 6; device 1 to give adduct 7. b Activation of device 1 for reaction with 4 takes place only when 1 is bound to chloride. c Progress of the reaction of 4 with imidazole (in blue), 2 (in mauve), 1 (in red), 1 + Bu4NCl (in green), and Bu4NCl (in black). The increase in absorbance at 327 nm, arising from the adduct 7, was monitored. The data are fitted to first-order kinetics to provide approximate observed rate constants (shown). d Switch-on of nucleophilic activity of 1 by the addition of chloride (3 equiv.) added after 193 min.
