Wednesday, March 7, 2012 at 10:33AM
Drew Wolfe

Aziridine

"Aziridines are organic compounds containing the aziridine functional group, a three-membered heterocycle with one amine group and two methylene groups.[3][4] The parent compound is aziridine (or ethylene imine), with molecular formula C2H5N."

"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 oxirane 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."

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