An air-stable radical with a redox-chameleonic amide. Issue 5 (16th December 2022)

• Record Type: Journal Article
• Authors: Peltier, Jesse L.; Serrato, Melinda R.; Thery, Valentin; Pecaut, Jacques; Tomás-Mendivil, Eder; Bertrand, Guy; Jazzar, Rodolphe; Martin, David
• Is Part Of: Chemical communications. Volume 59:Issue 5(2023)
• Page Start: 595
• Page End: 598
• Publication Date: 2022-12-16
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/d2cc05404c
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : Amides are redox stereoelectronic chameleons, which can act as strong acceptors and allow for the design of air-stable radicals. Abstract : 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.