Is Phenylnitrene a Missing Link in the Formation of Polycyclic Aromatic Nitrogen Heterocycles?
Year: 2025
Type: article
Abstract: The incorporation of heteroatoms into the framework of polycyclic aromatic hydrocarbons (PAHs), in particular of nitrogen to yield polycyclic aromatic nitrogen heterocycles (PANHs), has been proposed for both astronomical and combustion environments, but no suitable precursors and pathways have been found. Analogous pathways to PAH formation are kinetically or energetically inhibited in the presence of a nitrogen heteroatom. We report on the reaction of phenylnitrene ( 3 PhN, c ‐C 6 H 5 N) with resonance‐stabilized propargyl radicals (C 3 H 3 ) and find that the association reaction bifurcates depending on the orientation of the attacking propargyl radical and yields multiple isomeric products. Among them, we identify the condensed‐ring quinoline and conclude that nitrenes are viable candidates to drive the formation of PANHs.
Language: English
Subfield: Physical and Theoretical Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: hybrid
Estimated APC paid: $5,510
Funders: National Science Foundation, National Aeronautics and Space Administration, Deutscher Akademischer Austauschdienst, Deutsche Forschungsgemeinschaft, Bundesministerium für Bildung und Forschung, Nederlandse Organisatie voor Wetenschappelijk Onderzoek, Paul Scherrer Institut, Solar System Exploration Research Virtual Institute
OpenAlex ID: W4410121692