In organic chemistry, isodiazomethane, also known as isocyanamide, aminoisonitrile, or systematically as isocyanoamine, is the parent compound of a class of derivatives of general formula R₂N–NC. It has the condensed formula H₂N–N⁺≡C^–, making it an isomer of

diazomethane Diazomethane is the chemical compound CH2N2, discovered by German chemist Hans von Pechmann in 1894. It is the simplest diazo compound. In the pure form at room temperature, it is an extremely sensitive explosive yellow gas; thus, it is almost u ...

. It is prepared by protonating an ethereal solution of lithiodiazomethane, LiCHN₂, with aqueous NaH₂PO₄ or NH₄Cl. The parent compound is only marginally stable at room temperature and is isolated by removal of solvent at –50 °C. Derivatives are generally prepared by dehydration of the corresponding substituted formylhydrazine with COCl₂ and Et₃N. Earlier, the compound was misidentified as the isomeric

nitrilimine Nitrilimines or nitrile amides are a class of organic compounds sharing a common functional group with the general structure R-CN-NR corresponding to the conjugate base of an amine bonded to the N-terminus of a nitrile. The dominant structure for th ...

, HN^––N⁺≡CH. However, this structure was disproven by ¹H NMR studies, which show a compound with a single signal at δ 6.40 ppm in (CD₃CD₂)₂O instead of two signals expected for nitrilimine. Moreover, an

infrared Infrared (IR), sometimes called infrared light, is electromagnetic radiation (EMR) with wavelengths longer than those of visible light. It is therefore invisible to the human eye. IR is generally understood to encompass wavelengths from around ...

band at 2140 cm⁻¹ was assigned to the isocyano group. Transition metal complexes of isodiazomethane have been prepared. In bulk form isodiazomethane is a liquid which decomposes when the temperature exceeds 15 °C. If it is heated to 40 °C, the substance explodes. A solution of isodiazomethane in diethyl ether at –30 °C gradually isomerizes to diazomethane upon exposure to sodium hydroxide for 20 min.

Microwave spectroscopy Microwave spectroscopy is the spectroscopy method that employs microwaves, i.e. electromagnetic radiation at GHz frequencies, for the study of matter. History The ammonia molecule NH3 is shaped like a pyramid 0.38 Å in height, with an equilatera ...

indicates that unlike diazomethane, isodiazomethane is not completely planar, with the amino nitrogen undergoing inversion. An ''ab initio'' study indicated that there is some N–N double bond character in H₂N–N≡C, although less so than in the N–C bond of H₂N–C≡N. Like other

isocyanide An isocyanide (also called isonitrile or carbylamine) is an organic compound with the functional group –. It is the isomer of the related nitrile (–C≡N), hence the prefix is ''isocyano''.IUPAC Goldboo''isocyanides''/ref> The organic fragme ...

derivatives and

carbon monoxide Carbon monoxide (chemical formula CO) is a colorless, poisonous, odorless, tasteless, flammable gas that is slightly less dense than air. Carbon monoxide consists of one carbon atom and one oxygen atom connected by a triple bond. It is the simple ...

, its primary resonance form carries a negative charge and lone pair on carbon, a comparatively rare situation for neutral molecules. A resonance form with zero formal charge on all atoms also has some importance; however, the carbon atom only has a sextet of electrons and is formally a

carbene In organic chemistry, a carbene is a molecule containing a neutral carbon atom with a valence of two and two unshared valence electrons. The general formula is or where the R represents substituents or hydrogen atoms. The term "carbene" ma ...

References

{{Reflist Functional groups