Dihydroimidazol-2-ylidene
Encyclopedia
Dihydroimidazol-2-ylidene is a hypothetical organic compound
with formula C3H6N2. It would be a heterocyclic compound
, formally derived from imidazolidine
with two hydrogen atoms removed from carbon number 2, leaving two vacant chemical bond
s — which makes it a carbene
.
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
s. They include the first stable carbenes postulated (but not isolated) by Hans-Werner Wanzlick
around 1960.
They also include an example of the (saturated) imidazolin-2-ylidene (carbene
) reported by A.J. Arduengo in 1995.
Organic compound
An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...
with formula C3H6N2. It would be a heterocyclic compound
Heterocyclic compound
A heterocyclic compound is a cyclic compound which has atoms of at least two different elements as members of its ring. The counterparts of heterocyclic compounds are homocyclic compounds, the rings of which are made of a single element....
, formally derived from imidazolidine
Imidazolidine
Imidazolidine is a heterocyclic compound formally derived by the addition of four hydrogen atoms to imidazole. The intermediate, resulting from the addition of only two hydrogen atoms is called dihydroimidazole...
with two hydrogen atoms removed from carbon number 2, leaving two vacant chemical bond
Chemical bond
A chemical bond is an attraction between atoms that allows the formation of chemical substances that contain two or more atoms. The bond is caused by the electromagnetic force attraction between opposite charges, either between electrons and nuclei, or as the result of a dipole attraction...
s — which makes it a carbene
Carbene
In 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 RR'C:, but the carbon can instead be double-bonded to one group. The term "carbene" may also merely refer to the compound H2C:, also called...
.
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
Persistent carbene
A persistent carbene is a type of carbene demonstrating particular stability. The best-known examples are diaminocarbenes with the general formula 2C:, where the 'R's are various functional groups...
s. They include the first stable carbenes postulated (but not isolated) by Hans-Werner Wanzlick
Hans-Werner Wanzlick
Hans-Werner Wanzlick was a professor of chemistry at the Berlin Technical University. He is notable for work on persistent carbenes and for proposing the Wanzlick equilibrium between saturated imidazolin-2-ylidenes and their dimers — which he called "das doppelte Lottchen", after a 1949 novel by...
around 1960.
Carbene
In 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 RR'C:, but the carbon can instead be double-bonded to one group. The term "carbene" may also merely refer to the compound H2C:, also called...
) reported by A.J. Arduengo in 1995.