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Azanide - Wikipedia

From Wikipedia, the free encyclopedia

Anion derived from deprotonation of ammonia

This article is about the negative anion. For other compounds with the formula

NH2

but different charges, see

amino radical

and

nitrenium ion

.

Chemical compound

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°, nearly identical to the bond angle in the water molecule.

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.

  1. ^ a b Bergstrom, F. W. (1940). "Sodium Amide". Organic Syntheses. 20: 86. doi:10.15227/orgsyn.020.0086.
  2. ^ a b 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. ^ a b 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.

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