Oxamide is the

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

with the formula . This white

crystalline A crystal or crystalline solid is a solid material whose constituents (such as atoms, molecules, or ions) are arranged in a highly ordered microscopic structure, forming a crystal lattice that extends in all directions. In addition, macrosc ...

solid Solid is a state of matter where molecules are closely packed and can not slide past each other. Solids resist compression, expansion, or external forces that would alter its shape, with the degree to which they are resisted dependent upon the ...

is soluble in

ethanol Ethanol (also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound with the chemical formula . It is an Alcohol (chemistry), alcohol, with its formula also written as , or EtOH, where Et is the ps ...

, slightly soluble in

water Water is an inorganic compound with the chemical formula . It is a transparent, tasteless, odorless, and Color of water, nearly colorless chemical substance. It is the main constituent of Earth's hydrosphere and the fluids of all known liv ...

and insoluble in

diethyl ether Diethyl ether, or simply ether, is an organic compound with the chemical formula , sometimes abbreviated as . It is a colourless, highly Volatility (chemistry), volatile, sweet-smelling ("ethereal odour"), extremely flammable liquid. It belongs ...

. Oxamide is the diamide derived from

oxalic acid Oxalic acid is an organic acid with the systematic name ethanedioic acid and chemical formula , also written as or or . It is the simplest dicarboxylic acid. It is a white crystalline solid that forms a colorless solution in water. Its name i ...

, and the hydrate of

cyanogen Cyanogen is the chemical compound with the chemical formula, formula . Its structure is . The simplest stable carbon nitride, it is a Transparency and translucency, colorless and highly toxic gas with a pungency, pungent odor. The molecule is a ...

Preparation

Oxamide is produced from

hydrogen cyanide Hydrogen cyanide (formerly known as prussic acid) is a chemical compound with the chemical formula, formula HCN and structural formula . It is a highly toxic and flammable liquid that boiling, boils slightly above room temperature, at . HCN is ...

, which is oxidized to

, which is then hydrolyzed.. It can also be prepared from

formamide Formamide is an amide derived from formic acid. It is a colorless liquid which is miscible with water and has an ammonia-like odor. It is chemical feedstock for the manufacture of sulfa drugs and other pharmaceuticals, herbicides and pesticides, ...

by glow-discharge electrolysis.

Application

The main application is as a substitute for

urea Urea, also called carbamide (because it is a diamide of carbonic acid), is an organic compound with chemical formula . This amide has two Amine, amino groups (–) joined by a carbonyl functional group (–C(=O)–). It is thus the simplest am ...

in fertilizers. Oxamide hydrolyzes (releases ammonia) very slowly, which is sometimes preferred vs the quick release by urea. It is used as a stabilizer for nitrocellulose preparations. It also finds use in APCP

rocket motor A rocket engine is a reaction engine, producing thrust in accordance with Newton's third law by ejecting reaction mass rearward, usually a high-speed jet of high-temperature gas produced by the combustion of rocket propellants stored inside t ...

s as a high performance burn rate suppressant. The use of oxamide in concentrations of 1-3 wt% has shown to slow the linear burn rate while having minimal impact on propellant

specific impulse Specific impulse (usually abbreviated ) is a measure of how efficiently a reaction mass engine, such as a rocket engine, rocket using propellant or a jet engine using fuel, generates thrust. In general, this is a ratio of the ''Impulse (physics), ...

. ''N'',''N'-''substituted oxamides are supporting

ligands In coordination chemistry, a ligand is an ion or molecule with a 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 ...

for the copper-catalyzed amination and

amidation 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 any group, typically organyl groups or hydrogen atoms. The amide group is called a p ...

of aryl halides in Ullmann-Goldberg reaction, including relatively unreactive

aryl chloride In organic chemistry, an aryl halide (also known as a haloarene) is an aromatic compound in which one or more hydrogen atoms directly bonded to an aromatic ring are replaced by a halide ion (such as fluorine F''−'', chlorine Cl−1,−3,−5, bro ...

substrates.

Reactions

It dehydrates above 350 °C releasing

. Oxamide derivatives form

self-assembled monolayers Self-assembled monolayers (SAM) are assemblies of organic molecules that form spontaneously on surfaces by adsorption and organize themselves into more or less distinct domains (head group, chain/backbone, and tail/end group). In some cases, mole ...

consisting of a hydrogen bonded network.Nguyen T.L., Fowler F.W., Lauher J.W., "Commensurate and incommensurate hydrogen bonds. An exercise in crystal engineering." ''

Journal of the American Chemical Society The ''Journal of the American Chemical Society'' (also known as JACS) is a weekly peer-reviewed scientific journal that was established in 1879 by the American Chemical Society. The journal has absorbed two other publications in its history, the ...

'', 123(44), pp. 11057-64, 2001.

References

{{Authority control Carboxamides