Aziridinium

{{Short description|Ionic form of aziridines}} {{Chembox  | ImageFile = Aziridinium.svg | ImageSize = 150px  | IUPACName = aziridin-1-ium | OtherNames =  | Section1 = {{Chembox Identifiers | CASNo = 91127-35-4 | ChEBI = 50929 | ChEMBL = | ChemSpiderID = 10422370 | DrugBank = | EINECS = | EC_number = | Gmelin = 322803 | InChI = 1S/C2H5N/c1-2-3-1/h3H,1-2H2/p+1 | InChIKey = NOWKCMXCCJGMRR-UHFFFAOYSA-O | KEGG = | MeSHName = | PubChem = 23266392 | SMILES = C1C[NH2+]1 }} | Section2 = {{Chembox Properties |C=2|N=1|H=6|Formula_Charge = + | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} | Section3 = {{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }} '''Aziridiniums''' are the ionic form of the class of molecules known as aziridines.<ref name=":0">{{Cite journal |last1=Ranjith |first1=Jala |last2=Ha |first2=Hyun-Joon |date=22 March 2021 |title=Synthetic Applications of Aziridinium Ions |journal=Molecules |language=en |volume=26 |issue=6 |pages=1774 |doi=10.3390/molecules26061774 |pmid=33809951 |pmc=8004105 |issn=1420-3049|doi-access=free }}</ref>

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.<ref>{{Cite journal |last1=Baruah |first1=Bhupen |last2=Deuri |first2=Sanjib |last3=Phukan |first3=Prodeep |date=2014-01-01 |title=Reactivity and regioselectivity in the ring opening of 2-substituted non-activated aziridines: A density functional theory based analysis |url=https://www.sciencedirect.com/science/article/pii/S2210271X13004891 |journal=Computational and Theoretical Chemistry |language=en |volume=1027 |pages=197–202 |doi=10.1016/j.comptc.2013.11.005 |issn=2210-271X|url-access=subscription }}</ref> 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.<ref>{{Cite journal |last1=Paasche |first1=Alexander |last2=Arnone |first2=Mario |last3=Fink |first3=Reinhold F. |last4=Schirmeister |first4=Tanja |last5=Engels |first5=Bernd |date=2009-08-07 |title=Origin of the reactivity differences of substituted aziridines: CN vs CC bond breakages |journal=The Journal of Organic Chemistry |volume=74 |issue=15 |pages=5244–5249 |doi=10.1021/jo900505q |issn=1520-6904 |pmid=19719251}}</ref>

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.<ref name=":0" />

== References == {{Reflist}}

Category:Aziridines