Aziridinium
Names
IUPAC name
aziridin-1-ium
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
322803
  • InChI=1S/C2H5N/c1-2-3-1/h3H,1-2H2/p+1
    Key: NOWKCMXCCJGMRR-UHFFFAOYSA-O
  • C1C[NH2+]1
Properties
C2H6N+
Molar mass 44.076 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Aziridiniums are the ionic form of the class of molecules known as aziridines.[1]

Aziridines can be used to insert nitrogen atoms during synthesis, but without any substituents attached to the nitrogen in the ring, they are considered nonactivated and inert.[2] They can be rendered active by the preparation of aziridinium ions. The creation of this ionic species imparts a 47 kJ/mol ring strain increase.[3]

Thus, aziridiniums render nonactivated aziridines reactive, making them feasible to use in chemical synthesis. Although serving many synthetic purposes, aziridiniums served as key reagents that were used for the production of nitrogen mustard, a chemical warfare agent.[1]

References

  1. 1 2 Ranjith, Jala; Ha, Hyun-Joon (22 March 2021). "Synthetic Applications of Aziridinium Ions". Molecules. 26 (6): 1774. doi:10.3390/molecules26061774. ISSN 1420-3049. PMC 8004105. PMID 33809951.
  2. ↑ Baruah, Bhupen; Deuri, Sanjib; Phukan, Prodeep (2014-01-01). "Reactivity and regioselectivity in the ring opening of 2-substituted non-activated aziridines: A density functional theory based analysis". Computational and Theoretical Chemistry. 1027: 197–202. doi:10.1016/j.comptc.2013.11.005. ISSN 2210-271X.
  3. ↑ Paasche, Alexander; Arnone, Mario; Fink, Reinhold F.; Schirmeister, Tanja; Engels, Bernd (2009-08-07). "Origin of the reactivity differences of substituted aziridines: CN vs CC bond breakages". The Journal of Organic Chemistry. 74 (15): 5244–5249. doi:10.1021/jo900505q. ISSN 1520-6904. PMID 19719251.
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