Азиридин: қасиеттері, өндірілуі және қолданылуы

Organic ring compound with the formula (CH2)2NH
Chembox
| Watchedfields = changed
| verifiedrevid = 443409998
| ImageFileL1 = Aziridine. svg
| ImageFileR1 = Aziridine3d. png
| PIN = Aziridine
| SystematicName = Azacyclopropane
| OtherNames = AziraneEthylene imine Aminoethylene Dimethyleneimine Dimethylenimine Ethylimine
|Section1=
|Section2=Chembox Properties
| C=2 | H=5 | N=1
| Appearance = Colorless oily liquid
| Odor = ammonia like
| MeltingPtC = −77.9
| BoilingPtC = 56
| Solubility = miscible
| VaporPressure = 160 mmHg (20°C)
| REL = Ca
| LC50 = 250 ppm (rat, 1 hr)250 ppm (guinea pig, 1 hr)62 ppm (rat, 4 hr)223 ppm (mouse, 2 hr)56 ppm (rat, 2 hr)2236 ppm (mouse, 10 min) It is a colorless, toxic, volatile liquid that is of significant practical interest. Aziridine was discovered in 1888 by the chemist Siegmund Gabriel. Its derivatives, also referred to as aziridines, are of broader interest in medicinal chemistry.

The bond angles in aziridine are approximately 60°, considerably less than the normal hydrocarbon bond angle of 109.5°, which results in angle strain as in the comparable cyclopropane and ethylene oxide molecules. A banana bond model explains bonding in such compounds. Aziridine is less basic than acyclic aliphatic amines, with a pKa of 7.9 for the conjugate acid, due to increased s character of the nitrogen free electron pair. Angle strain in aziridine also increases the barrier to nitrogen inversion. This barrier height permits the isolation of separate invertomers, for example the cis and trans invertomers of N chloro 2 methylaziridine.

Aziridine is produced industrially from aminoethanol via two related routes. The Nippon Shokubai process requires an oxide catalyst and high temperatures to effect the dehydration. In the Wenker synthesis, the aminoethanol is converted to the sulfate ester, which undergoes base induced sulfate elimination. Older methods entailed amination of 1,2 dichloroethane and cyclization of 2 chloroethylamine.