Imidazol‐2‐ylidene: Generation of a Missing Carbene and Its Dication by Neutralization–Reionizatin and Charge‐Stripping Mass Spectrometry

Abstract

Though not yet available off-the-shelf, the generation the title molecule 2 from aldehyde 1 and its detection in the gas phase confirms quantum chemical predictions that it should be stable, in particular towards its 1,2-hydrogen shift isomer imidazole. Thus, substituents larger than hydrogen on the nitrogen atoms are not a feature essential to the inherent stability of imidazolylidene carbenes, although such groups may still play a role in hindering bimolecular processes (N = neutralization, R = reionization).