Structure via PubChem · Public domain (PubChem)
aziridine
Sign in to saveAlso known as Ethyleneimine, Aminoethylene, Azirane, Dimethyleneimine, Dimethylenimine, Ethylenimine, Ethylimine, EI
Aziridine is an organic compound consisting of the three-membered heterocycle . 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.
Chemical data
- Formula
- C2H5N
- Molecular weight
- 43.07 g/mol
- IUPAC name
- aziridine
- SMILES
- C1CN1
- InChIKey
- NOWKCMXCCJGMRR-UHFFFAOYSA-N
- XLogP
- -0.4
- Polar surface area
- 21.9 Ų
- H-bond donors
- 1
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 43.042
Show 16 more facts
- immediately dangerous to life or health
- 176
- chemical formula
- C₂H₅N
- density
- 0.83
- Commons category
- Aziridine
- NIOSH Pocket Guide ID
- 0274
- melting point
- -77.95
- boiling point
- 56
- vapor pressure
- 160
- flash point
- 12
- lower flammable limit
- 3.3
- upper flammable limit
- 54.8
- ionization energy
- 9.20
- ceiling exposure limit
- 0
- canonical SMILES
- C1CN1
- pKa
- 8.01
- electric dipole moment
- 1.90
via Wikidata · CC0
~2 min read
Article
5 sectionsContents
- Structure
- Synthesis and uses
- Safety
- See also
- References
Aziridine is an organic compound consisting of the three-membered heterocycle . 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.
== Structure == 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.