In organic chemistry, isodiazomethane, also known as isocyanamide, aminoisonitrile, or systematically as isocyanoamine,[1] is the parent compound of a class of derivatives of general formula R2N–NC.
[2] The parent compound is only marginally stable at room temperature and is isolated by removal of solvent at –50 °C.
[6] A solution of isodiazomethane in diethyl ether at –30 °C gradually isomerizes to diazomethane upon exposure to sodium hydroxide for 20 min.
[4] Microwave spectroscopy indicates that unlike diazomethane, isodiazomethane is not completely planar, with the amino nitrogen undergoing inversion.
[8] Like other isocyanide derivatives and carbon monoxide, its primary resonance form carries a negative charge and lone pair on carbon, a comparatively rare situation for neutral molecules.