{{Short description|Anion derived from deprotonation of ammonia}} {{About|the negative anion|other compounds with the formula {{chem2|NH2}} but different charges|amino radical|and|nitrenium ion}} {{Chembox | Name = Amide anion | ImageFile = Azanide-ion-3D-vdW.png | SystematicName = | pronounce = {{IPAc-en|ˈ|æ|z|ə|n|aɪ|d}} | IUPACName = Azanide | OtherNames = {{ubl|Amide|Amide ion|Ammonia ion|Ammonide|Dihydrogen azanide|Dihydrogen nitride|Monoamide}} | Section1 = {{Chembox Identifiers | CASNo = 17655-31-1 | CASNo_Comment = | ChEBI = 29337 | ChemSpiderID = 2104824 | PubChem = 2826723 | PubChem_Comment = | SMILES = [NH2-] | SMILES_Comment = | SMILES1 = [N-] | InChI = 1S/H2N/h1H2/q-1 | InChI_Comment = | InChIKey = HYGWNUKOUCZBND-UHFFFAOYSA-N }} | Section2 = {{Chembox Properties | Properties_ref = | H=2 | N=1 | Formula = {{chem2|NH2−}} | MeltingPt_ref = | ConjugateAcid = Ammonia }} | Section3 = {{Chembox Structure | MolShape = Bent }} | Section4 = | Section5 = | Section6 = | Section8 = {{Chembox Related | OtherFunction = water, fluoronium | OtherFunction_label = isoelectronic | OtherAnions = {{ubl|Phosphanide|Arsinide|Imide|Nitride|Nitridohydride}} }} }} '''Azanide''' is the IUPAC-sanctioned name for the anion {{chem2|NH2-}}. The term is obscure; derivatives of {{chem2|NH2-}} are almost invariably referred to as '''amides''',<ref name = amideNa/><ref name=amideLi/><ref name=amideK/> despite the fact that amide also refers to the organic functional group –{{chem2|C(\dO)\sNR2}}. The anion {{chem2|NH2-}} 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 isoelectronic water molecule.
==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):<ref name = amideNa>{{ cite journal| author = Bergstrom, F. W. | title = Sodium Amide | journal=Organic Syntheses| year = 1940 | volume = 20 | pages = 86| doi=10.15227/orgsyn.020.0086}}</ref><ref name="amideLi">{{cite book|author=P. W. Schenk|chapter=Lithium amide|title=Handbook of Preparative Inorganic Chemistry, 2nd Ed. |editor=G. Brauer|publisher=Academic Press|year=1963|place=New York, NY|volume=1|pages=454}}</ref><ref>{{ Cite book |author1=Greenlee, K. W. |author2=Henne, A. L. |title=Inorganic Syntheses |chapter = Sodium Amide | year = 1946 | volume = 2 | pages = 128–135 | doi = 10.1002/9780470132333.ch38 |isbn=9780470132333 }}</ref><!-- notice the titles of these classic articles, amide, not azanide-->
:{{chem2|2 M + 2 NH3 → 2 MNH2 + H2}}, where M = Li, Na, K
Silver(I) amide ({{chem2|AgNH2}}) is prepared similarly.<ref name=amideK>{{cite book|author=O. Glemser, H. Sauer|chapter=Silver Amide <!--includes prep of KNH2-->|title=Handbook of Preparative Inorganic Chemistry |edition=2nd |editor=G. Brauer|publisher=Academic Press|year=1963|place=New York, NY|volume=1|pages=1043}}</ref>
Transition metal complexes of the amido ligand are often produced by salt metathesis reaction or by deprotonation of metal ammine complexes.
==References== {{Reflist}}
Category:Anions Category:Nitrogen hydrides Category:Nitrogen(−III) compounds