# Aziridinium

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> Markdown URL: https://mediated.wiki/source/Aziridinium.md
> Source: https://en.wikipedia.org/wiki/Aziridinium
> Source revision: 1301012988
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{{Short description|Ionic form of aziridines}}
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| ImageFile = Aziridinium.svg
| ImageSize = 150px
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| IUPACName = aziridin-1-ium
| OtherNames = 
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| 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 = +
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| Density = 
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| Section3 = {{Chembox Hazards
| MainHazards = 
| FlashPt = 
| AutoignitionPt = 
  }}
}}
'''Aziridiniums''' are the ionic form of the class of molecules known as [aziridines](/source/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](/source/nitrogen_mustard), a chemical warfare agent.<ref name=":0" />

== References ==
{{Reflist}}

Category:Aziridines

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Adapted from the Wikipedia article [Aziridinium](https://en.wikipedia.org/wiki/Aziridinium) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Aziridinium?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.