Aminohydroxymethylene (H2N-C̈-OH), the Simplest Aminooxycarbene.

We generated and isolated hitherto unreported aminohydroxymethylene (1, aminohydroxycarbene) in solid Ar via pyrolysis of oxalic acid monoamide (2). Astrochemically relevant carbene 1 is persistent under cryogenic conditions and only decomposes to HNCO + H2 and NH3 + CO upon irradiation of the matrix at 254 nm. This photoreactivity is contrary to other hydroxycarbenes and aminomethylene, which undergo [1,2]H shifts to the corresponding carbonyls or imine. The experimental data are well supported by the results of CCSD(T)/cc-pVTZ and B3LYP/6-311++G(3df,3pd) computations.