Azanide is the

IUPAC The International Union of Pure and Applied Chemistry (IUPAC ) is an international federation of National Adhering Organizations working for the advancement of the chemical sciences, especially by developing nomenclature and terminology. It is ...

-sanctioned name for the anion . The term is obscure; derivatives of are almost invariably referred to as amides, despite the fact that

amide In organic chemistry, an amide, also known as an organic amide or a carboxamide, is a compound with the general formula , where R, R', and R″ represent organic groups or hydrogen atoms. The amide group is called a peptide bond when it is ...

also refers to the organic

functional group In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the res ...

–. The anion is the conjugate base of

ammonia Ammonia is an inorganic compound of nitrogen and hydrogen with the formula . A stable binary hydride, and the simplest pnictogen hydride, ammonia is a colourless gas with a distinct pungent smell. Biologically, it is a common nitrogenous wa ...

, 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°.

Alkali metal derivatives

The alkali metal derivatives are best known, although usually referred to as alkali metal amides. Examples include

lithium amide Lithium amide or lithium azanide is an inorganic compound with the chemical formula . It is a white solid with a tetragonal crystal structure. Lithium amide can be made by treating lithium metal with liquid ammonia: : Other lithium amides The con ...

sodium amide Sodium amide, commonly called sodamide (systematic name sodium azanide), is the inorganic compound with the formula . It is a salt composed of the sodium cation and the azanide anion. This solid, which is dangerously reactive toward water, is whit ...

, and

potassium amide Potassium amide is an inorganic compound with the chemical formula . Like other alkali metal amides, it is a white solid that hydrolyzes readily. It is a strong base. Production Potassium amide is produced by the reaction of ammonia with potassium ...

. These salt-like solids are produced by treating

liquid ammonia Ammonia is an inorganic compound of nitrogen and hydrogen with the formula . A stable binary hydride, and the simplest pnictogen hydride, ammonia is a colourless gas with a distinct pungent smell. Biologically, it is a common nitrogenous wa ...

with strong bases or directly with the alkali metals (blue liquid ammonia solutions due to the

solvated electron A solvated electron is a free electron in (solvated in) a solution, and is the smallest possible anion. Solvated electrons occur widely. Often, discussions of solvated electrons focus on their solutions in ammonia, which are stable for days, but s ...

): :, where M = Li, Na, K

Silver(I) amide Silver is a chemical element with the symbol Ag (from the Latin ', derived from the Proto-Indo-European ''h₂erǵ'': "shiny" or "white") and atomic number 47. A soft, white, lustrous transition metal, it exhibits the highest electrical cond ...

() is prepared similarly. Transition

metal complex A coordination complex consists of a central atom or ion, which is usually metallic and is called the ''coordination centre'', and a surrounding array of bound molecules or ions, that are in turn known as ''ligands'' or complexing agents. Man ...

es of the

amido In organic chemistry, an amide, also known as an organic amide or a carboxamide, is a compound with the general formula , where R, R', and R″ represent organic groups or hydrogen atoms. The amide group is called a peptide bond when it is ...

ligand In coordination chemistry, a ligand is an ion or molecule (functional group) that binds to a central metal atom to form a coordination complex. The bonding with the metal generally involves formal donation of one or more of the ligand's electro ...

are often produced by

salt metathesis reaction A salt metathesis reaction, sometimes called a double displacement reaction, is a chemical process involving the exchange of bonds between two reacting chemical species which results in the creation of products with similar or identical bonding ...

or by

deprotonation Deprotonation (or dehydronation) is the removal (transfer) of a proton (or hydron, or hydrogen cation), (H+) from a Brønsted–Lowry acid in an acid–base reaction.Henry Jakubowski, Biochemistry Online Chapter 2A3, https://employees.csbsju.edu ...

metal ammine complex In coordination chemistry, metal ammine complexes are metal complexes containing at least one ammonia () ligand. "Ammine" is spelled this way due to historical reasons; in contrast, alkyl or aryl bearing ligands are spelt with a single "m". Almost ...

es.

References

{{Reflist Anions Nitrogen hydrides