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In chemistry imidines are a rare
In chemistry imidines are a rare 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 rest ...
, being the nitrogen analogues of anhydrides
An organic acid anhydride is an acid anhydride that is an organic compound. An acid anhydride is a compound that has two acyl groups bonded to the same oxygen atom. A common type of organic acid anhydride is a carboxylic anhydride, where the p ...
and imide
In organic chemistry, an imide is a functional group consisting of two acyl groups bound to nitrogen. The compounds are structurally related to acid anhydrides, although imides are more resistant to hydrolysis. In terms of commercial applications, ...
s. They were first reported by Adolf Pinner
Adolf Pinner (August 31, 1842 – May 21, 1909) was a German chemist.
Early life and education
He was educated at the Jewish Theological Seminary of Breslau, Jewish Theological Seminary at Breslau and at the University of Berlin (Phd in Chemis ...
in 1883, but did not see significant investigation until the 1950s, when Patrick Linstead
Sir (Reginald) Patrick Linstead CBE, DSc, HonDSc, DIC, HonFCGI, HonMIMM, FRS (28 August 1902, in London – 22 September 1966, in London) was an English chemist.
Biography
Patrick Linstead was born on 28 August 1902 in Southgate, London, the seco ...
and John Arthur Elvidge developed a number of compounds.
Imidines may be prepared in a modified Pinner reaction
The Pinner reaction refers to the acid catalysed reaction of a nitrile with an alcohol to form an imino ester salt (alkyl imidate salt); this is sometimes referred to as a Pinner salt.
The reaction is named after Adolf Pinner, who first described ...
, by passing hydrogen chloride into an alcoholic solution of their corresponding di-nitriles
In organic chemistry, a nitrile is any organic compound that has a functional group. The prefix ''cyano-'' is used interchangeably with the term ''nitrile'' in industrial literature. Nitriles are found in many useful compounds, including met ...
(i.e. succinonitrile
Succinonitrile, also butanedinitrile, is a nitrile, with the formula of C2H4(CN)2. It is a colorless waxy solid which melts at 58 °C.
Succinonitrile is produced by the addition of hydrogen cyanide to acrylonitrile (hydrocyanation):
:CH2=C ...
, glutaronitrile
Glutaronitrile, also pentanedinitrile, is a nitrile
In organic chemistry, a nitrile is any organic compound that has a functional group. The prefix ''cyano-'' is used interchangeably with the term ''nitrile'' in industrial literature. Nitril ...
, adiponitrile
Adiponitrile is an organic compound with the chemical formula (CH2)4(CN)2. This viscous, colourless dinitrile is an important precursor to the polymer nylon 66. In 2005, about one million tonnes of adiponitrile were produced.M. T. Musser, "Adipi ...
) to give imino ethers which then condense when treated with ammonia. As a result, most structures are cyclic
Cycle, cycles, or cyclic may refer to:
Anthropology and social sciences
* Cyclic history, a theory of history
* Cyclical theory, a theory of American political history associated with Arthur Schlesinger, Sr.
* Social cycle, various cycles in soc ...
.
The compounds are highly moisture sensitive and can be converted into imide
In organic chemistry, an imide is a functional group consisting of two acyl groups bound to nitrogen. The compounds are structurally related to acid anhydrides, although imides are more resistant to hydrolysis. In terms of commercial applications, ...
s upon exposure to water.
See also
*Amidine
Amidines are organic compounds with the functional group RC(NR)NR2, where the R groups can be the same or different. They are the imine derivatives of amides (RC(O)NR2). The simplest amidine is formamidine, HC(=NH)NH2.
Examples of amidines includ ...
*Guanidines
Guanidine is the compound with the formula HNC(NH2)2. It is a colourless solid that dissolves in polar solvents. It is a strong base that is used in the production of plastics and explosives. It is found in urine predominantly in patients experie ...
References
{{Reflist Functional groups