Aziridinium

Aziridinium
Names
	IUPAC name aziridin-1-ium
Identifiers
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:50929;
ChemSpider	10422370;
Gmelin Reference	322803
PubChem CID	23266392;
	InChI InChI=1S/C2H5N/c1-2-3-1/h3H,1-2H2/p+1 Key: NOWKCMXCCJGMRR-UHFFFAOYSA-O;
	SMILES C1C[NH2+]1;
Properties
Chemical formula	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, or "mustard gas", a chemical warfare agent.[1]

References

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.
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.
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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[:0-1] 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.