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Aziridinium
Aziridinium is the ionic form of the class of molecules known as aziridines. 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, aziridinium ions render nonactivated aziridines reactive, making them feasible to use in chemical synthesis. Although serving many synthetic purposes, aziridinium ions served as key reagents that were used for the production of nitrogen mustard, or "mustard gas Mustard gas or sulfur mustard is a chemical compound belonging to a family of cytotoxic and blister agents known as mustard agents. The name ''mustard gas'' is technically incorrect: the substance, when dispersed, is often not actually a gas, b ...", a chemical warfare agent. References {{Reflist Aziridines ...
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Aziridines
220 px, chemotherapeutic agent by virtue of its antitumour activity. Aziridines are organic compounds containing the aziridine functional group, a three-membered heterocycle with one amine (-NR-) and two methylene bridges (--). The parent compound is aziridine (or ethylene imine), with molecular formula . Several drugs feature aziridine rings, including mitomycin C, porfiromycin, and azinomycin B (carzinophilin). Structure The bond angles in aziridine are approximately 60°, considerably less than the normal hydrocarbon bond angle of 109.5°, which results in angle strain as in the comparable cyclopropane and ethylene oxide molecules. A banana bond model explains bonding in such compounds. Aziridine is less basic than acyclic aliphatic amines, with a pKa of 7.9 for the conjugate acid, due to increased s character of the nitrogen free electron pair. Angle strain in aziridine also increases the barrier to nitrogen inversion. This barrier height permits the isolation of sepa ...
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Nitrogen Mustard
Nitrogen mustards are cytotoxic organic compounds with the chloroethylamine (Cl(CH2)2NR2) functional group. Although originally produced as chemical warfare agents, they were the first chemotherapeutic agents for treatment of cancer. Nitrogen mustards are nonspecific DNA alkylating agents. Chemical warfare During World War II nitrogen mustards were studied at the Yale School of Medicine by Alfred Gilman and Louis Goodman, and classified human clinical trials of nitrogen mustards for the treatment of lymphoma started in December 1942. Also during World War II, an incident during the air raid on Bari, Italy, led to the release of mustard gas that affected several hundred soldiers and civilians. Medical examination of the survivors showed a decreased number of lymphocytes. After World War II was over, the Bari incident and the Yale group's studies eventually converged prompting a search for other similar compounds. Due to its use in previous studies, the nitrogen mustard known ...
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Mustard Gas
Mustard gas or sulfur mustard is a chemical compound belonging to a family of cytotoxic and blister agents known as mustard agents. The name ''mustard gas'' is technically incorrect: the substance, when dispersed, is often not actually a gas, but is instead in the form of a fine mist of liquid droplets.https://www.acs.org/content/dam/acsorg/education/resources/highschool/chemmatters/gc-mustard-gas-personal-safety-and-natl-security.pdf Mustard gases form blisters on exposed skin and in the lungs, often resulting in prolonged illness ending in death. The active ingredient in typical mustard gas is the organosulfur compound bis(2-chloroethyl) sulfide. In the wider sense, compounds with the structural element are known as ''sulfur mustards'' and ''nitrogen mustards'', respectively. Such compounds are potent alkylating agents, which can interfere with several biological processes. History as chemical weapons As a chemical weapon, mustard gas was first used in World War I, and has ...
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