Artikel: Aziridine GudangMovies21 Rebahinxxi

• Source: Aziridine

Aziridine is an organic compound consisting of the three-membered heterocycle C2H5N. It is a colorless, toxic, volatile liquid that is of significant practical interest. Aziridine was discovered in 1888 by the chemist Siegmund Gabriel. Its derivatives, also referred to as aziridines, are of broader interest in medicinal chemistry.




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 separate invertomers, for example the cis and trans invertomers of N-chloro-2-methylaziridine.




Synthesis and uses



Aziridine is produced industrially from aminoethanol via two related routes. The Nippon Shokubai process requires an oxide catalyst and high temperatures to effect the dehydration. In the Wenker synthesis, the aminoethanol is converted to the sulfate ester, which undergoes base-induced sulfate elimination. Older methods entailed amination of 1,2-dichloroethane and cyclization of 2-chloroethylamine.
Aziridine forms a wide variety of polymeric derivatives, known as polyethylenimines (PEI). These and related species are useful crosslinking agents and precursors for coatings.




Safety


Aziridine is highly toxic with an LD50 of 14 mg (oral, rats). It is a skin irritant. As an alkylating agent, it is also a mutagen. It is reactive toward DNA, potentially relevant to its mutagenicity. Aziridine containing compounds also appear to be similarly dangerous.




See also


Binary ethylenimine, a dimeric form of aziridine




References

Kata Kunci Pencarian:

• Aziridine
• Aziridines
• Wenker synthesis
• Blum–Ittah aziridine synthesis
• Johnson–Corey–Chaykovsky reaction
• De Kimpe aziridine synthesis
• Borirane
• Oximide
• Mitomycins
• Carbonyl condensation

Artikel Terkait "aziridine"

Aziridine - 9002-98-6, C2H5N, density, melting point, boiling point ...

29 Apr 2024 · Aziridine - cas 9002-98-6, synthesis, structure, density, melting point, boiling point

Aziridine - Wikipedia

Aziridine is an organic compound consisting of the three-membered heterocycle C 2 H 5 N. [5] [6] It is a colorless, toxic, volatile liquid that is of significant practical interest. [7] Aziridine was discovered in 1888 by the chemist Siegmund Gabriel. [8] Its derivatives, also referred to as aziridines, are of broader interest in medicinal ...

Aziridine

Aziridine is a saturated organic heteromonocyclic parent, a member of aziridines and an azacycloalkane. It has a role as an alkylating agent. It is a conjugate base of an aziridinium.

1-butylaziridine - 1120-85-0, C6H13N, density, melting point, …

29 Apr 2024 · Synthesis Reference(s): The Journal of Organic Chemistry, 14, p. 605, 1949 DOI: 10.1021/jo01156a015: Physical Properties for CAS 1120-85-0:

Aziridines - Wikipedia

In organic chemistry, aziridines are organic compounds containing the aziridine functional group (chemical structure (R−) 4 C 2 N−R), a three-membered heterocycle with one amine (>NR) and two methylene bridges (>CR 2).

Aziridine - an overview | ScienceDirect Topics

Aziridines, the nitrogenous analogs of epoxides, are a group of natural and/or synthetic organic compounds sharing the aziridine functional group which is a three-membered heterocycle with one amine group and two methylene groups.

Recent updates and future perspectives in aziridine synthesis and ...

13 Jul 2023 · In this review, selected recent advances in the preparation and reactivity of aziridines using modern synthetic approaches are highlighted, while comparing these new strategies with more classical approaches.

Aziridine: Properties, Reactions, Production And Uses

08 Agu 2024 · Aziridine, also known as ethylenimine, is a saturated heterocyclic amine with the formula C 2 H 5 N. It is a colorless, volatile liquid with a strong, unpleasant odor that is highly reactive due to the strain in its three-membered ring.

Aziridine - Re-evaluation of Some Organic Chemicals, Hydrazine …

Aziridine produces genetic damage in bacteria, insects and mammalian cells in culture, as well as dominant lethal effects in mice. Opening of the aziridine ring appears to be an important metabolic step in its mutagenic action.

Aziridine alkaloids as potential therapeutic agents

01 Sep 2009 · The present review describes research on natural aziridine alkaloids isolated from both terrestrial and marine species, as well as their lipophilic semi-synthetic, and/or synthetic analogs.