Imidazolidine

Imidazolidine
Structural formula of imidazolidine
Ball-and-stick model of imidazolidine
Names
IUPAC name
Imidazolidine
Other names
Tetrahydroimidazole
Identifiers
504-74-5 Yes
ChemSpider 396007 
Jmol-3D images Image
PubChem 449488
Properties
Molecular formula
C3H8N2
Molar mass 72.11 g·mol−1
Supplementary data page
Refractive index (n),
Dielectric constant (εr), etc.
Thermodynamic
data
Phase behaviour
solidliquidgas
UV, IR, NMR, MS
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
  verify (what is: Yes/?)
Infobox references

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 imidazoline (dihydroimidazole). The connection of imidazolidine to related compounds is indicated in the Figure.

Figure. Chemical relationship of imidazole to its reduced derivatives.

Formally, removal of the two hydrogens at carbon 2 (between the two nitrogens) would yield the carbene dihydroimidazol-2-ylidene. Derivatives of the latter comprise an important class of persistent carbenes.[1]

Unsubstituted imidazolidines are not stable compounds and are prone to rapid decomposition.[2] The first unsubstituted imidazolidine synthesis was reported in 1952 [3]

References

  1. A. J. Arduengo, H. V. R. Dias, R. L. Harlow, and M. Kline (1992). "Electronic stabilization of nucleophilic carbenes". J. Am. Chem. Soc. 114 (14): 5530. doi:10.1021/ja00040a007.
  2. J. Org. Chem. 32 (12): 4103–4105. 1967. doi:10.1021/jo01287a100. Missing or empty |title= (help)
  3. E. D. Bergmann, E. Meeron, Y. Hirschberg (1952). Rec. Trau. Chim. 11 (200). Missing or empty |title= (help)