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Encyclopedia > Aziridine
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Aziridine parent compound
Aziridine parent compound

Aziridines are a group of organic compounds sharing the aziridine functional group which is a three membered heterocycle with one amine group and two methylene groups 1,2. The parent compound of the aziridines is called aziridine with molecular formula C2H5N. Jump to: navigation, search An organic compound is any member of a large class of chemical compounds whose molecules contain carbon, with exception of carbides, carbonates, carbon oxides and gases containing carbon. ... In ecology functional groups are collections of organisms based on morphological, physiological, behavioral, biochemical, or environmental responses or on trophic criteria. ... Heterocycles are organic chemical structures containing non-carbon elements. ... Ammonia Amines are organic compounds containing nitrogen as the key atom in the amine functional group. ... In chemistry, methylene is a divalent functional group CH2 derived formally from methane. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ...

Contents


Structure

The bond angles in aziridine are around 60° which is considerably shorter than the bond angle of 109.5° found in ordinary hydrocarbons and this results in angle strain just like in the comparable cyclopropane and oxirane molecules. Bonding in this type of compound can be explained by invoking a banana bond model. 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. Increased angle strain in aziridine is also responsible for increased barrier for nitrogen inversion. This barrier is high enough for the isolation of separate invertomers for instance the cis and trans invertomers of N-chloro-2-methylaziridine. Geometry of the water molecule Molecules have fixed equilibrium geometries--bond lengths and angles--that are dictated by the laws of quantum mechanics. ... Jump to: navigation, search // Definition In chemistry, a hydrocarbon is any chemical compound that consists only of the elements carbon (C) and hydrogen (H). ... The presence of angle strain in a molecule indicates that in a specific chemical conformation there exists a bond angle that deviates from the bond angle required to archieve maximum bond strength. ... Molecule structure formula of cyclopropane Cyclopropane is a cycloalkane molecule with the molecular formula C3H6 consisting of three carbon atoms linked to each other to form a ring, with each carbon atom bearing two hydrogen atoms. ... The common (Arrhenius) definition of a base is a chemical compound that either donates hydroxide ions or absorbs hydrogen ions when dissolved in water. ... Acyclic can mean any of the following: In chemistry, an acyclic compound is a hydrocarbon compound having an open chain. ... In chemistry, non-aromatic and non-cyclic (acyclic) organic compounds are called aliphatic. ... In chemistry and biochemistry, acid dissociation constant, the acidity constant, or the acid-ionization constant () is a specific type of equilibrium constant that indicates the extent of dissociation of hydrogen ions from an acid. ... In the Brønsted-Lowry (protonic) theory of acids and bases, a conjugate acid is the acid member, HX, of a pair of two compounds that transform into each other by gain or loss of a proton. ... In chemistry, hybridisation is the mixing of atomic orbitals to form new orbitals suitable for bonding. ... Jump to: navigation, search General Name, Symbol, Number nitrogen, N, 7 Chemical series nonmetals Group, Period, Block 15, 2, p Appearance colorless Atomic mass 14. ... A lone pair is an electron pair without bonding or sharing with other atoms. ... The presence of angle strain in a molecule indicates that in a specific chemical conformation there exists a bond angle that deviates from the bond angle required to archieve maximum bond strength. ... In chemistry, a nitrogen compound like ammonia in a trigonal pyramid geometry undergoes rapid nitrogen inversion whereby the molecule turns inside out. ... In chemistry, geometric isomerism is a form of stereoisomerism and describes the orientation of functional groups at the ends of a bond around which no rotation is possible. ... In chemistry, geometric isomerism is a form of stereoisomerism and describes the orientation of functional groups at the ends of a bond around which no rotation is possible. ...


Synthesis

Aziridines can be prepared in organic synthesis in several ways. Organic synthesis is the construction of organic molecules via chemical processes. ...


Cyclization of haloamines

An amine functional group displaces the adjacent halide in an intramolecular nucleophilic substitution reaction to generate an aziridine. Amino alcohols have the same reactivity but it is required to convert the hydroxy group into a good leaving group first. Ammonia Amines are organic compounds containing nitrogen as the key atom in the amine functional group. ... A halide is a binary compound, of which one part is a halogen atom and the other part is an element or radical that is less electronegative than the halogen, to make a fluoride, chloride, bromide, iodide, or astatide compound. ... Intramolecular describes a process or characteristic limited within the structure of a single, or each molecule; a property or phenomenon limited to the extent of a single, or each molecule. ... Jump to: navigation, search In chemistry, nucleophilic substitution is a class of substitution reaction in which an electron-rich nucleophile attacks a molecule and replaces a group or atom, called the leaving group. ... This prefix in chemical nomenclature indicates the presence of a hydroxyl functional group (-OH). ... A leaving group is an atom or molecule that detaches from an organic molecule, which, after detachment, is called the residual or main part. ...


Nitrene addition

Nitrene addition to alkenes is a well established method for the synthesis of aziridines. Photolysis or thermolysis of azides are a good way to generate nitrenes. Nitrenes can also be prepared in-situ from iodosobenzene diacetate and sulfonamides or the ethoxycarbonylnitrene from the N-sulfonyloxy precursor 3. In chemistry, a nitrene (R-N:) is the nitrogen analogue of a (carbon carbene). ... Jump to: navigation, search An alkene in organic chemistry is an unsaturated hydrocarbon containing at least one carbon to carbon double bond. ... Jump to: navigation, search Photolysis refers to any chemical reaction in which a compound is broken down by light. ... Jump to: navigation, search Thermolysis (from thermo- meaning heat and -lysis meaning break down) is a chemical process by which a subtance is decomposed into other substances by use of heat. ... Jump to: navigation, search An azide is a N3- anion, or a reactive group in organic chemistry where a carbon substituent is attached as RN3. ... Sulfonamides, also known as sulfa drugs, are synthetic antimicrobial agents derived from sulfonic acid. ...

Nitrene addition

Triazoline decomposition

On thermal treatment or photolysis of triazolines, nitrogen is expelled and an aziridine remains. The required triazoline is generated from reaction of an azide with an alkene in a cycloaddition reaction. Jump to: navigation, search General Name, Symbol, Number nitrogen, N, 7 Chemical series nonmetals Group, Period, Block 15, 2, p Appearance colorless Atomic mass 14. ... Jump to: navigation, search An azide is a N3- anion, or a reactive group in organic chemistry where a carbon substituent is attached as RN3. ... Jump to: navigation, search An alkene in organic chemistry is an unsaturated hydrocarbon containing at least one carbon to carbon double bond. ... A Cycloaddition is a pericyclic reaction in which the net result is loss of two pi bonds and gain of two sigma bonds. ...


Reactions

Nucleophilic ring opening

Aziridines are reactive substrates in ring opening reactions with many nucleophiles due to their ring strain. Alcoholysis and aminolysis are basically the reverse reactions of the cyclizations. Effective nucleophiles are also carbon nucleophiles such as organolithium reagent and organocuprates. In chemistry, a nucleophile (literally nucleus lover) is a reagent which is attracted to centres of positive charge. ... Ring strain is an organic chemistry term that describes the destabilization of a cyclic molecule—such as a cycloalkane—due to the non-favorable high energy spatial orientations of its atoms. ... An organolithium reagent is any organic compound with a direct bond between a carbon and a lithium atom. ...


References

  • 1 Heterocyclic chemistry T.L. Gilchrist ISBN 0582014212
  • 2 Epoxides and aziridines - A mini review Albert Padwaa and S. Shaun Murphreeb Arkivoc (JC-1522R) pp 6-33 Online article
  • 3 Addition reactions of ethoxycarbonylnitrene and ethoxycarbonylnitrenium ion to allylic ethers M. Antonietta Loreto, Lucio Pellacani, Paolo A. Tardella, and Elena Toniato Tetrahedron Letters, Volume 25, Issue 38 , 1984, Pages 4271-4274 Abstract

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Methamphetamine from Ephedrine: I. Chloroephedrines and Aziridines (1306 words)
The respective aziridines were prepared from the chloro analogs by addition of concentrated sodium hydroxide (NaOH), with gentle warming, allowing the aziridine to volatilize into a hanging drop of dilute hydrochloric acid.
The principal impurities in the conversion of ephedrine to methamphetamine which we have analyzed from clandestine samples are the unreduced chloro analog of ephedrine and 1,2-dimethyl-3-phenyl aziridine.
Similarly, (-)chloroephedrine (derived from (+)pseudoephedrine) rearranges to trans-1,2-dimethyl-3-phenyl aziridine [7].
Polyfunctional aziridines for use in crosslinking applications - Patent 4563307 (4592 words)
the bis aziridine of the diacrylate of the adduct of neopentyl glycol and 2 moles of ethylene oxide,
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