Imidazolidine

Imidazolidine

Names
IUPAC name Imidazolidine
Other names Tetrahydroimidazole 1,3-diazolidine
Identifiers
CAS Number	504-74-5
ChemSpider	396007
Jmol interactive 3D	Image
PubChem	449488
InChI InChI=1S/C3H8N2/c1-2-5-3-4-1/h4-5H,1-3H2 Key: WRYCSMQKUKOKBP-UHFFFAOYSA-N InChI=1/C3H8N2/c1-2-5-3-4-1/h4-5H,1-3H2 Key: WRYCSMQKUKOKBP-UHFFFAOYAC
SMILES N1CCNC1
Properties
Chemical formula	C3H8N2
Molar mass	72.109
Supplementary data page
Structure and properties	Refractive index (n), Dielectric constant (εr), etc.
Thermodynamic data	Phase behaviour solid–liquid–gas
Spectral data	UV, IR, NMR, MS
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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. Hirshberg, and S. Pinchas (1952). Rec. Trav. Chim. 71 (2): 200–212. doi:10.1002/recl.19520710211. Missing or empty |title= (help)