Aziridinium
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Aziridiniums are the ionic form of the class of molecules known as
aziridines 220 px, chemotherapy.html" ;"title="Mitomycin C, an aziridine, is used as a chemotherapy">chemotherapeutic agent by virtue of its antitumour activity. In organic chemistry, aziridines are organic compounds containing the aziridine functional gr ...
. 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. 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. 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 Nitrogen mustards (NMs) are cytotoxic organic compounds with the bis(2-chloroethyl)amino ((ClC2H4)2NR) functional group. Although originally produced as chemical warfare agents, they were the first chemotherapeutic agents for treatment of canc ...
, a chemical warfare agent.


References

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