Structure via PubChem · Public domain (PubChem)
diaziridine
Sign in to saveA diaziridine is a heterocyclic compound containing two nitrogen atoms in a three-membered ring. Diaziridines can be considered as strained hydrazines. Unlike most amine types of structures, the nitrogen atoms of diaziridines are configurationally stable because the ring strain prevents Walden inversion. As a result, there can be various stereoisomeric forms of this structure.
Chemical data
- Formula
- CH4N2
- Molecular weight
- 44.056 g/mol
- IUPAC name
- diaziridine
- SMILES
- C1NN1
- InChIKey
- DIXBSCZRIZDQGC-UHFFFAOYSA-N
- XLogP
- -0.6
- Polar surface area
- 43.9 Ų
- H-bond donors
- 2
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 44.037448
Show 3 more facts
- canonical SMILES
- C1NN1
- chemical formula
- CH₄N₂
- Commons category
- Diaziridine
Sources (1)
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- Reactions
- References
A diaziridine is a heterocyclic compound containing two nitrogen atoms in a three-membered ring. Diaziridines can be considered as strained hydrazines. Unlike most amine types of structures, the nitrogen atoms of diaziridines are configurationally stable because the ring strain prevents Walden inversion. As a result, there can be various stereoisomeric forms of this structure.
They are usually synthesized by treating a carbonyl compound with an aminating reagent like hydroxylamine-O-sulfonic acid and either ammonia or a primary aliphatic amine under slightly basic conditions. The final step is based on the intramolecular cyclization of an aminal.
Excerpted from Wikipedia’s “diaziridine” article, available under the CC BY-SA 4.0 licence.