An air-stable radical with a redox-chameleonic amide

An air-stable (amino)(amido)radical was synthesized by reacting a cyclic (alkyl)(amino)carbene with carbazoyl chloride, followed by one-electron reduction. We show that an adjacent radical center weakens the amide bond. It enables the amino group to act as a strong acceptor under steric contraint, thus enhancing the stabilizing capto-dative effect.

Automated summary

An air-stable (amino)(amido)radical was prepared by the reaction of a cyclic (alkyl)(amino)carbene with carbazoyl chloride, followed by one-electron reduction. The neighboring radical center was found to weaken the amide bond, enabling the amino group to serve as a strong acceptor under steric constraint and enhancing the stabilizing captodative effect.