Capture of Electrochemically Generated Fleeting Carbazole Radical Cations and Elucidation of Carbazole Dimerization Mechanism by Mass Spectrometry
Chengyuan Liu, Qi Wang, B. Hivick, Yongling Ai, Pier Alexandre Champagne, Yang Pan, Hao Chen
Abstract
The capture of reactive intermediates is important for the elucidation of reaction mechanisms. We report the first observation of electrochemically generated, short-lived radical cations of carbazole (t1/2 ≈ 97 μs) and two N-substituted carbazole derivatives by mass spectrometry. In addition, online investigation of the reactivity of electrochemically generated carbazole radical cations supports that the carbazole dimerization mechanism involves the reaction of one radical cation with one neutral molecule rather than the previously proposed coupling of two radical cations.
Topics & Concepts
ChemistryCarbazoleMass spectrometryRadical ionReactivity (psychology)PhotochemistryReaction mechanismMoleculeComputational chemistryCombinatorial chemistryIonOrganic chemistryCatalysisPathologyMedicineAlternative medicineChromatographyRadical Photochemical ReactionsCO2 Reduction Techniques and CatalystsCatalytic C–H Functionalization Methods