Gas Phase Identification of the Elusive N‑Hydroxyoxaziridine (c‑H₂CON(OH)): A Chiral Molecule

The hitherto elusive N-hydroxyoxaziridine molecule (c-H₂CON­(OH)), a chiral, high energy isomer of nitromethane (CH₃NO₂) and one of the simplest representatives of an oxaziridine, is detected in the gas phase. Electronic structure calculations propose an impending synthesis eventually via addition of carbene (CH₂) to the nitrogen–oxygen double bond of nitrous acid (HONO). The oxaziridine ring demonstrates an unusual kinetic stability toward ring opening compared to the isoeletronic cyclopropane (C₃H₆) counterpart. This system defines a fundamental benchmark to explore the formation and stability of racemic derivatives of strained oxaziridines (c-H₂CONH) and changes our perception how we think about fundamental decomposition and isomerization mechanisms in (model compounds of) energetic materials.