Azanide

This article is about the negative anion. For other compounds with the formula NH₂ but different charges, see amino radical and nitrenium ion.

Azanide is the IUPAC-sanctioned name for the anion NH−2. The term is obscure; derivatives of NH−2 are almost invariably referred to as amides,^[1][2][3] despite the fact that amide also refers to the organic functional group –C(=O)−NR₂. The anion NH−2 is the conjugate base of ammonia, so it is formed by the self-ionization of ammonia. It is produced by deprotonation of ammonia, usually with strong bases or an alkali metal. Azanide has a H–N–H bond angle of 104.5°.

Amide anion

Names
Pronunciation	/ˈæzənaɪd/
IUPAC name Azanide
Other names Amide Amide ion Ammonia ion Ammonide Dihydrogen azanide Dihydrogen nitride Monoamide
Identifiers
CAS Number	17655-31-1
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:29337
ChemSpider	2104824
PubChem CID	2826723
CompTox Dashboard (EPA)	DTXSID80385105
InChI InChI=1S/H2N/h1H2/q-1 Key: HYGWNUKOUCZBND-UHFFFAOYSA-N
SMILES [NH2-] [N-]
Properties
Chemical formula	NH−2
Molar mass	16.023 g·mol−1
Conjugate acid	Ammonia
Structure
Molecular shape	Bent
Related compounds
Other anions	Phosphanide Arsinide Imide Nitride Nitridohydride
Related isoelectronic	water, fluoronium
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Alkali metal derivatives

The alkali metal derivatives are best known, although usually referred to as alkali metal amides. Examples include lithium amide, sodium amide, and potassium amide. These salt-like solids are produced by treating liquid ammonia with strong bases or directly with the alkali metals (blue liquid ammonia solutions due to the solvated electron):^[1][2][4]

2 M + 2 NH₃ → 2 MNH₂ + H₂, where M = Li, Na, K

Silver(I) amide (AgNH₂) is prepared similarly.^[3]

Transition metal complexes of the amido ligand are often produced by salt metathesis reaction or by deprotonation of metal ammine complexes.

References

1. Bergstrom, F. W. (1940). "Sodium Amide". Organic Syntheses. 20: 86. doi:10.15227/orgsyn.020.0086.
2. P. W. Schenk (1963). "Lithium amide". In G. Brauer (ed.). Handbook of Preparative Inorganic Chemistry, 2nd Ed. Vol. 1. New York, NY: Academic Press. p. 454.
3. O. Glemser, H. Sauer (1963). "Silver Amide". In G. Brauer (ed.). Handbook of Preparative Inorganic Chemistry. Vol. 1 (2nd ed.). New York, NY: Academic Press. p. 1043.
4. Greenlee, K. W.; Henne, A. L. (1946). "Sodium Amide". Inorganic Syntheses. Vol. 2. pp. 128–135. doi:10.1002/9780470132333.ch38. ISBN 9780470132333.