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| Names | |||
|---|---|---|---|
| Preferred IUPAC name Imidazolidine[1] | |||
| Systematic IUPAC name 1,3-Diazacyclopentane | |||
| Other names Tetrahydroimidazole 1,3-Diazolidine | |||
| Identifiers | |||
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3D model (JSmol) | |||
| 102462 | |||
| ChEBI | |||
| ChemSpider |
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| UNII | |||
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| Properties | |||
| C3H8N2 | |||
| Molar mass | 72.109 | ||
| Supplementary data page | |||
| Imidazolidine (data page) | |||
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |||
Imidazolidine is aheterocyclic 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. Imidazolidines are cyclic 5-membered examples of the general class ofaminals.
Imidazolidines are traditionally prepared bycondensation reaction of 1,2-diamines andaldehydes. Most commonly, one or both nitrogen center is substituted with an alkyl orbenzyl (Bn) group:[2]
The first unsubstituted imidazolidine synthesis was reported in 1952.[3]
Unsubstituted imidazolidines are often labile.[4] The rings are susceptible to hydrolysis back to the diamine and the aldehyde.[2]
Formally, removal of the two hydrogens at carbon 2 (between the two nitrogens) would yield thecarbenedihydroimidazol-2-ylidene. Derivatives of the latter comprise an important class ofpersistent carbenes.[5]
Classified as adiamine, it is formally derived by the addition of four hydrogen atoms toimidazole. The intermediate, resulting from the addition of only two hydrogen atoms is calledimidazoline (dihydroimidazole). The connection of imidazolidine to related compounds is indicated in the Figure.
