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Acyl Cyanide
In organic chemistry, an acyl cyanide is a functional group with the formula and structure . It consists of an acyl group () attached to cyanide (). Examples include acetyl cyanide, formyl cyanide, and oxalyl dicyanide. Acyl cyanides are reagents in organic synthesis. Synthesis Classically acyl cyanides are produced by the salt metathesis reaction of acyl chlorides with sodium cyanide: :\ce + \ce \longrightarrow + \ce Alternatively, they can be produced by dehydration of acyl aldoximes: :\ce\ce \longrightarrow + \ce Acetyl cyanide is also prepared by hydrocyanation of ketene: :\ce + \ce \longrightarrow \ce Reactions They are mild acylating agents. With aqueous base, acyl cyanides break down to cyanide and the carboxylate: : + \ce \longrightarrow \ce + \ce + \ce With azides, acyl cyanides undergo the click reaction to give acyl tetrazole Tetrazoles are a class of synthetic organic heterocyclic compound, consisting of a 5-member ring of four nitrogen atom ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Acyl Cyanide
In organic chemistry, an acyl cyanide is a functional group with the formula and structure . It consists of an acyl group () attached to cyanide (). Examples include acetyl cyanide, formyl cyanide, and oxalyl dicyanide. Acyl cyanides are reagents in organic synthesis. Synthesis Classically acyl cyanides are produced by the salt metathesis reaction of acyl chlorides with sodium cyanide: :\ce + \ce \longrightarrow + \ce Alternatively, they can be produced by dehydration of acyl aldoximes: :\ce\ce \longrightarrow + \ce Acetyl cyanide is also prepared by hydrocyanation of ketene: :\ce + \ce \longrightarrow \ce Reactions They are mild acylating agents. With aqueous base, acyl cyanides break down to cyanide and the carboxylate: : + \ce \longrightarrow \ce + \ce + \ce With azides, acyl cyanides undergo the click reaction to give acyl tetrazole Tetrazoles are a class of synthetic organic heterocyclic compound, consisting of a 5-member ring of four nitrogen atom ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Sodium Cyanide
Sodium cyanide is a poisonous compound with the formula Na C N. It is a white, water-soluble solid. Cyanide has a high affinity for metals, which leads to the high toxicity of this salt. Its main application, in gold mining, also exploits its high reactivity toward metals. It is a moderately strong base. Production and chemical properties Sodium cyanide is produced by treating hydrogen cyanide with sodium hydroxide: :HCN + NaOH → NaCN + H2O Worldwide production was estimated at 500,000 tons in the year 2006. Formerly it was prepared by the Castner process involving the reaction of sodium amide with carbon at elevated temperatures. : NaNH2 + C → NaCN + H2 The structure of solid NaCN is related to that of sodium chloride. The anions and cations are each six-coordinate. Potassium cyanide (KCN) adopts a similar structure. When treated with acid, it forms the toxic gas hydrogen cyanide: : NaCN + H+ → HCN + Na+ Because the salt is derived from a weak aci ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Functional Groups
In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the rest of the molecule's composition. This enables systematic prediction of chemical reactions and behavior of chemical compounds and the design of chemical synthesis. The reactivity of a functional group can be modified by other functional groups nearby. Functional group interconversion can be used in retrosynthetic analysis to plan organic synthesis. A functional group is a group of atoms in a molecule with distinctive chemical properties, regardless of the other atoms in the molecule. The atoms in a functional group are linked to each other and to the rest of the molecule by covalent bonds. For repeating units of polymers, functional groups attach to their nonpolar core of carbon atoms and thus add chemical character to carbon chains. Functi ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Tetrazole
Tetrazoles are a class of synthetic organic heterocyclic compound, consisting of a 5-member ring of four nitrogen atoms and one carbon atom. The name tetrazole also refers to the parent compound with formula CH2N4, of which three isomers can be formulated. Structure and bonding Three isomers of the parent tetrazole exist, differing in the position of the double bonds: 1''H''-, 2''H''-, and 5''H''-tetrazole. The 1''H''- and 2''H''- isomers are tautomers, with the equilibrium lying on the side of 1''H''-tetrazole in the solid phase. In the gas phase, 2''H''-tetrazole dominates. These isomers can be regarded as aromatic, with 6 π-electrons, while the 5''H''-isomer is nonaromatic. Synthesis 1''H''-Tetrazole was first prepared by the reaction of anhydrous hydrazoic acid and hydrogen cyanide under pressure. Treatment of organic nitriles with sodium azide in the presence of iodine or silica-supported sodium bisulfate as a heterogeneous catalyst enables an advantageous synthesis ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Click Reaction
In chemical synthesis, click chemistry is a class of biocompatible small molecule reactions commonly used in bioconjugation, allowing the joining of substrates of choice with specific biomolecules. Click chemistry is not a single specific reaction, but describes a way of generating products that follow examples in nature, which also generates substances by joining small modular units. In many applications, click reactions join a biomolecule and a reporter molecule. Click chemistry is not limited to biological conditions: the concept of a "click" reaction has been used in chemoproteomic, pharmacological, and various biomimetic applications. However, they have been made notably useful in the detection, localization and qualification of biomolecules. Click reactions occur in one pot, are not disturbed by water, generate minimal and inoffensive byproducts, and are "spring-loaded"—characterized by a high thermodynamic driving force that drives it quickly and irreversibly to high yiel ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Azides
In chemistry, azide is a linear, polyatomic anion with the formula and structure . It is the conjugate base of hydrazoic acid . Organic azides are organic compounds with the formula , containing the azide functional group. The dominant application of azides is as a propellant in air bags. Preparation Sodium azide is made industrially by the reaction of nitrous oxide, with sodium amide in liquid ammonia as solvent: : Many inorganic azides can be prepared directly or indirectly from sodium azide. For example, lead azide, used in detonators, may be prepared from the metathesis reaction between lead nitrate and sodium azide. An alternative route is direct reaction of the metal with silver azide dissolved in liquid ammonia. Some azides are produced by treating the carbonate salts with hydrazoic acid. Bonding Azide is isoelectronic with carbon dioxide , cyanate , nitrous oxide , nitronium ion and cyanogen fluoride NCF. Per valence bond theory, azide can be described by sever ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Carboxylate
In organic chemistry, a carboxylate is the conjugate base of a carboxylic acid, (or ). It is an ion with negative charge. Carboxylate salts are salts that have the general formula , where M is a metal and ''n'' is 1, 2,...; ''carboxylate esters'' have the general formula (or ). R and R′ are organic groups; R′ ≠ H. Synthesis Carboxylate ions can be formed by deprotonation of carboxylic acids. Such acids typically have p''K''a of less than 5, meaning that they can be deprotonated by many bases, such as sodium hydroxide or sodium bicarbonate. :RCOOH + NaOH -> RCOONa + H2O Resonance stabilization of the carboxylate ion Carboxylic acids easily dissociate into a carboxylate anion and a positively charged hydrogen ion (proton), much more readily than alcohols do (into an alkoxide ion and a proton), because the carboxylate ion is stabilized by resonance. The negative charge that is left after deprotonation of the carboxyl group is delocalized between ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Acylation
In chemistry, acylation (or alkanoylation) is the chemical reaction in which an acyl group () is added to a compound. The compound providing the acyl group is called the acylating agent. Because they form a strong electrophile when treated with some metal catalysts, acyl halides are commonly used as acylating agents. For example, Friedel–Crafts acylation uses acetyl chloride (ethanoyl chloride or ) as the agent and aluminum chloride () as a catalyst to add an ethanoyl ( acetyl) group to benzene: The mechanism of this reaction is electrophilic aromatic substitution. Acyl halides and acid anhydrides of carboxylic acids are also commonly used acylating agents. In some cases, active esters exhibit comparable reactivity. All react with amines to form amides and with alcohols to form esters by nucleophilic acyl substitution. Acylation can be used to prevent rearrangement reactions that would normally occur in alkylation. To do this an acylation reaction is performed, then the ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Ketene
In organic chemistry, a ketene is an organic compound of the form , where R and R' are two arbitrary monovalent chemical groups (or two separate substitution sites in the same molecule). The name may also refer to the specific compound ethenone , the simplest ketene. Although they are highly useful, most ketenes are unstable. When used as reagents in a chemical procedure, they are typically generated when needed, and consumed as soon as (or while) they are produced. History Ketenes were first studied as a class by Hermann Staudinger before 1905. Ketenes were systematically investigated by Hermann Staudinger in 1905 in the form of diphenylketene (conversion of \alpha-chlorodiphenyl acetyl chloride with zinc). Staudinger was inspired by the first examples of reactive organic intermediates and stable radicals discovered by Moses Gomberg in 1900 (compounds with triphenylmethyl group). Properties Ketenes are highly electrophilic at the carbon atom bonded with the heteroatom, ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Hydrocyanation
In organic chemistry, hydrocyanation is a process for conversion of alkenes to nitriles. The reaction involves the addition of hydrogen cyanide and requires a catalyst. This conversion is conducted on an industrial scale for the production of precursors to nylon. Hydrocyanation of unactivated alkenes Industrially, hydrocyanation is commonly performed on alkenes catalyzed by nickel complexes of phosphite () ligands. A general reaction is shown:Piet W.N.M. van Leeuwen "Homogeneous Catalysis: Understanding the Art", 2004, Wiley-VCH, Weinheim. :RCH=CH2 + HCN -> RCH2-CH2-CN Stoichiometry and mechanism The reaction involves the addition of and cyanide () to the substrate. Usually the substrate is an alkene and the product is a nitrile. The reaction proceeds via the oxidative addition of HCN to a low-valent metal complex to give a hydrido cyanide complex. Subsequent binding of the alkene gives the intermediate , which then undergoes migratory insertion to give an alkylmetal cya ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Aldoxime
In organic chemistry, an oxime is a organic compound belonging to the imines, with the general formula , where R is an organic side-chain and R’ may be hydrogen, forming an aldoxime, or another organic group, forming a ketoxime. O-substituted oximes form a closely related family of compounds. Amidoximes are oximes of amides () with general structure . Oximes are usually generated by the reaction of hydroxylamine with aldehydes () or ketones (). The term ''oxime'' dates back to the 19th century, a combination of the words ''oxygen'' and ''imine''. Structure and properties If the two side-chains on the central carbon are different from each other—either an aldoxime, or a ketoxime with two different "R" groups—the oxime can often have two different geometric stereoisomeric forms according to the ''E''/''Z'' configuration. An older terminology of ''syn'' and ''anti'' was used to identify especially aldoximes according to whether the R group was closer or further from the ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Dehydration Reaction
In chemistry, a dehydration reaction is a chemical reaction that involves the loss of water from the reacting molecule or ion. Dehydration reactions are common processes, the reverse of a hydration reaction. Dehydration reactions in organic chemistry Esterification The classic example of a dehydration reaction is the Fischer esterification, which involves treating a carboxylic acid with an alcohol to give an ester :RCO2H + R′OH RCO2R′ + H2O Often such reactions require the presence of a dehydrating agent, i.e. a substance that reacts with water. Etherification Two monosaccharides, such as glucose and fructose, can be joined together (to form saccharose) using dehydration synthesis. The new molecule, consisting of two monosaccharides, is called a disaccharide. Nitrile formation Nitriles are often prepared by dehydration of primary amides. :RC(O)NH2 → RCN + H2O Ketene formation Ketene is produced by heating acetic acid and trapping the product: :CH3CO2H → CH2=C= ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
