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

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journal contribution
posted on 23.06.2020, 22:03 by Santosh K. Singh, Tang-Yu Tsai, Bing-Jian Sun, Agnes H. H. Chang, Alexander M. Mebel, Ralf I. Kaiser
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.