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Encyclopedia > Azide

An azide is the N3- anion, the anion of hydrazoic acid or a reactive group in organic chemistry where a carbon substituent is attached as RN3. The azido group is the corresponding N3 organic functional group [1]. Hydrazoic acid is a colorless, volatile, and extremely explosive liquid at room temperature and pressure. ... In organic chemistry functional groups are specific groups of atoms within molecules, that are responsible for the characteristic chemical reactions of those molecules. ...

Contents


Azide anion

The anion's structure is:

N-=N+=N-

with a net charge of -1. Heavy metal azides, such as lead azide are very explosive when heated or shaken. Sodium azide (NaN3) is used in airbags. The azide anion is toxic, inhibiting the function of cytochrome c oxidase by binding irreversibly to the heme cofactor, in a process similar to that of carbon monoxide. The term heavy metal may have various more general or more specific meanings. ... Lead azide (Pb(N3)2) is an explosive and toxic crystalline compound. ... Sodium azide (NaN3) is a highly toxic chemical that exists as an odorless white solid. ... An automobile airbag, like this one in a crashed SEAT Ibiza car, deflates after 0. ... Cytochrome c oxidase The enzyme cytochrome c oxidase (PDB 2OCC, EC 1. ... Carbon monoxide, chemical formula CO, is a colorless, odorless, tasteless, and highly toxic gas. ...


Organic azides

Organic azides engage in useful organic reactions. They are relatively stable substituents, and act as nucleophiles on the terminal nitrogen (usually liberating nitrogen after cycloreversion reactions), and have electron-donating character for the neighboring carbon. An azide can easily expulse diatomic nitrogen, a property which is exploited in many reactions such as the Staudinger Ligation or the Curtius rearrangement or for example in the synthesis of γ-imino-β-enamino esters [2]. In the azide alkyne Huisgen cycloaddition azides react as 1,3-dipoles. Organic reactions are chemical reactions between organic compounds. ... In chemistry, a nucleophile (literally nucleus lover) is a reagent which is attracted to centres of positive charge. ... General Name, Symbol, Number nitrogen, N, 7 Chemical series nonmetals Group, Period, Block 15, 2, p Appearance colorless Atomic mass 14. ... The Staudinger ligation (also called the Staudinger reaction) is a chemical reaction in which the combination of an azide with a phosphine or phosphite produces a phosphorimidate. ... The Curtius rearrangement, as first defined by Theodor Curtius, is a chemical reaction that involves the rearrangement of an acyl azide to a isocyanate. ... The Azide alkyne Huisgen cycloaddition is a Huisgen cycloaddition or 1,3-dipolar cycloaddition between an azide and a terminal alkyne to a 1,2,3-triazole. ... A 1,3-dipole is a type of organic compound with a three-atom pi-electron system containing 4 electrons delocalized over three atoms. ...

γ-imino-β-enamino esters: Reaction conditions: a) sodium azide 4 eq., acetone, 18 hrs reflux 92% chemical yield b) isopropyl amine, Titanium tetrachloride, diethyl ether 14 hrs. reflux 83% yield. Azide 2 is formed in a nucleophilic aliphatic substitution reaction displacing chlorine in 1 by the azide anion. The ketone reacts with the amine to an imine which tautomerizes to the enamine in 4. In the next rearrangement reaction nitrogen is expulsed and a proton transferred to 6. The last step is another tautomerization with the formation of the enamine 7 as a mixture of cis and trans isomers
γ-imino-β-enamino esters: Reaction conditions: a) sodium azide 4 eq., acetone, 18 hrs reflux 92% chemical yield b) isopropyl amine, Titanium tetrachloride, diethyl ether 14 hrs. reflux 83% yield. Azide 2 is formed in a nucleophilic aliphatic substitution reaction displacing chlorine in 1 by the azide anion. The ketone reacts with the amine to an imine which tautomerizes to the enamine in 4. In the next rearrangement reaction nitrogen is expulsed and a proton transferred to 6. The last step is another tautomerization with the formation of the enamine 7 as a mixture of cis and trans isomers

Examples of organic azides: Image File history File links Iminoenaminoester. ... Sodium azide (NaN3) is a highly toxic chemical that exists as an odorless white solid. ... In chemistry, acetone (also known as propanone, dimethyl ketone, 2-propanone, propan-2-one and β-ketopropane) is the simplest representative of the ketones. ... The hour (symbol: h) is a unit of time. ... Diagram of typical reflux apparatus. ... Yield in chemistry, also known as chemical yield and reaction yield, is the amount of product obtained in a chemical reaction. ... Ammonia Amines are organic compounds and a type of functional group that contain nitrogen as the key atom. ... Titanium tetrachloride (TiCl4) is used for commercial production of pure titanium metal. ... Diethyl ether, also known as ether and ethoxyethane, is a clear, colorless, and highly flammable liquid with a low boiling point and a characteristic smell. ... 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. ... Ketone group A ketone is either the functional group characterized by a carbonyl group linked to two other carbon atoms or a chemical compound that contains this functional group. ... Ammonia Amines are organic compounds and a type of functional group that contain nitrogen as the key atom. ... An imine is a functional group or chemical compound containing a carbon-nitrogen double bond. ... Tautomers are organic compounds that are interconvertible by a chemical reaction called tautomerization. ... An enamine is an unsaturated compound derived by the reaction of an aldehyde or ketone with a secondary amine followed by loss of H2O. Form Categories: Functional groups | Stub ... A rearrangement reaction is a broad class of organic reactions where the carbon skeleton of a molecule is rearranged to give a structural isomer of the original molecule. ... 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. ...

Chemical structure of Tetramethylsilane Chemical structure of a Trimethylsilyl group The name Tetramethylsilane stands for a chemical compound whose molecular structure is essentially like a silane (SiH4) molecule with four methyl groups substituted for the four hydrogen atoms in it. ...

Safety

  • Sodium azide is toxic (LD50 oral (rats) = 27 mg/kg) and can be absorbed through the skin.
  • Sodium azide decomposes explosively upon heating to above 275 °C (hence its use in airbags in the automotive industry).
  • Sodium azide reacts vigorously with CS2, bromine, nitric acid, dimethyl sulfate, and a series of heavy metals, including copper and lead.
  • In reaction with water or Brønsted acids the highly toxic and explosive hydrogen azide is released.
  • It has been reported that sodium azide and polymer-bound azide reagents react with dichloromethane and chloroform to form di- and triazidomethane resp., which are both unstable in high concentrations in solution. Various devastating explosions were reported while reaction mixtures were being concentrated on a rotary evaporator. The hazards of diazidomethane (and triazidomethane) have been well documented by A. Hassner et al. [3].
  • Heavy-metal azides that are highly explosive under pressure or shock are formed when solutions of sodium azide or HN3 vapors come into contact with heavy metals or their salts. Heavy-metal azides can accumulate under certain circumstances, for example, in metal pipelines and on the metal components of diverse equipment (rotary evaporators, freezedrying equipment, cooling traps, water baths, waste pipes), and thus lead to violent explosions. Some organic and other covalent azides are classified as highly explosive and toxic (inorganic azides as neurotoxins; azide ions as cytochrome c oxidase (COX) inhibitors).
  • Solid iodoazide is explosive and should not be prepared in the absence of solvent. [4].

An LD50 test being administered In toxicology, the LD50 or colloquially semilethal dose of a particular substance is a measure of how much constitutes a lethal dose. ... An airbag is a flexible membrane or envelope, inflatable to contain air or some other gas. ... Carbon disulfide (CS2) is a colorless liquid with a pleasant odor that is like the smell of chloroform. ... General Name, Symbol, Number bromine, Br, 35 Chemical series halogens Group, Period, Block 17, 4, p Appearance gas/liquid: red-brown solid: metallic luster Atomic mass 79. ... The chemical compound nitric acid (HNO3), otherwise known as aqua fortis or spirit of nitre, is a colorless, corrosive liquid, a toxic acid which can cause severe burns. ... Dimethyl sulfate has chemical formula (CH3)2SO4. ... General Name, Symbol, Number copper, Cu, 29 Chemical series transition metals Group, Period, Block 11, 4, d Appearance metallic pinkish red Atomic mass 63. ... General Name, Symbol, Number lead, Pb, 82 Chemical series poor metals Group, Period, Block 14, 6, p Appearance bluish white Atomic mass 207. ... A Brønsted-Lowry acid (sometimes shortened to Brønsted acid) is an acid that donates a hydrogen ion to another compound, called a Brønsted-Lowry base. ... Hydrazoic acid is a colorless, volatile, and extremely explosive liquid at room temperature and pressure. ... Dichloromethane or Methylene chloride is a chemical compound widely used as a solvent for organic materials. ... Chloroform, also known as trichloromethane and methyl trichloride, is a chemical compound with formula CHCl3. ... Rotavapor stands short for rotary evaporator. ... Freeze drying (also known as Lyophilization) is a dehydration process typically used to preserve a perishable material, or to make the material more convenient for transport. ... Cytochrome c oxidase The enzyme cytochrome c oxidase (PDB 2OCC, EC 1. ...

External links

  • http://www.azides.org
  • Synthesis of organic azides - Recent methods

References

  1. ^ Review: S. Bräse, C. Gil, K. Knepper, V. Zimmermann, Angew. Chem. 2005, 117, 5320-5374; Angew. Chem. Int. Ed. 2005, 44, 5188-5240.
  2. ^ An efficient synthesis of γ-imino- and γ-amino-β-enamino esters Sven Mangelinckx, Pieter Van Vooren, David De Clerck, Ferenc Fülöp, and Norbert De Kimpea Arkivoc JC-1560E 2005 Online Article
  3. ^ A. Hassner et al., Angew. Chem. Int. Ed. Engl., 25, 479 (1986), J. Org. Chem., 55, 2304 (1990).
  4. ^ L. Marinescu, J. Thinggaard, I. B. Thomsen, M. Bols, J. Org. Chem. 2003, 68, 9453 – 9455.

  Results from FactBites:
 
Azide - Wikipedia, the free encyclopedia (608 words)
The azide anion is toxic, inhibiting the function of cytochrome c oxidase by binding irreversibly to the heme cofactor, in a process similar to that of carbon monoxide.
Azide 2 is formed in a nucleophilic aliphatic substitution reaction displacing chlorine in 1 by the azide anion.
It has been reported that sodium azide and polymer-bound azide reagents react with dichloromethane and chloroform to form di- and triazidomethane resp., which are both unstable in high concentrations in solution.
Sodium azide - Wikipedia, the free encyclopedia (614 words)
Sodium azide is also used as a chemical preservative in hospitals and laboratories, in agriculture (farming) for pest control, and in detonators and other explosives.
Azide anions prevent the cells of the body from using oxygen, inhibiting the function of cytochrome oxidase by binding irreversibly to the heme cofactor in a process similar to that of carbon monoxide.
Sodium azide is more harmful to the heart and the brain than to other organs, because the heart and the brain use a lot of oxygen.
  More results at FactBites »

 
 

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