Dihydroimidazol-2-ylidene is a hypothetical
organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. T ...
with formula C
3H
6N
2. It would be a
heterocyclic compound, formally derived from
imidazolidine
Imidazolidine is a heterocyclic compound (CH2)2(NH)2CH2. The parent imidazolidine is lightly studied, but related compounds substituted on one or both nitrogen centers are more common. Generally, they are colorless, polar, basic compounds. Imida ...
with two hydrogen atoms removed from carbon number 2, leaving two vacant
chemical bond
A chemical bond is a lasting attraction between atoms or ions that enables the formation of molecules and crystals. The bond may result from the electrostatic force between oppositely charged ions as in ionic bonds, or through the sharing of ...
s — which makes it a
carbene
In organic chemistry, a carbene is a molecule containing a neutral carbon atom with a valence of two and two unshared valence electrons. The general formula is or where the R represents substituents or hydrogen atoms.
The term "carbene" ma ...
.
Although carbenes in general are extremely short-lived, some derivatives of this compound are surprisingly stable, and form an important class of the
persistent carbene
A persistent carbene (also known as stable carbene) is a type of carbene demonstrating particular stability. The best-known examples and by far largest subgroup are the ''N''-heterocyclic carbenes (NHC) (sometimes called Arduengo carbenes), for ex ...
s. They include the first stable carbenes postulated (but not isolated) by
Hans-Werner Wanzlick around 1960.
![SIMes](https://upload.wikimedia.org/wikipedia/commons/3/3d/SIMes.png)
They also include an example of the (saturated) imidazolin-2-ylidene (
carbene
In organic chemistry, a carbene is a molecule containing a neutral carbon atom with a valence of two and two unshared valence electrons. The general formula is or where the R represents substituents or hydrogen atoms.
The term "carbene" ma ...
) reported by
A.J. Arduengo in 1995.
References
Carbenes
Imidazolines
Hypothetical chemical compounds
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