An acyl halide (also known as an acid halide) is a chemical compound derived from an acid by replacing a hydroxyl group with a halide group. A chemical compound is a substance consisting of two or more different elements chemically bonded together in a fixed proportion by Mass. In Computer science, ACID ( Atomicity Consistency Isolation Durability) is a set of properties that guarantee that Database transactions are Hydroxyl in Chemistry stands for a molecule consisting of an Oxygen atom and a Hydrogen atom connected by a Covalent bond. 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 [1]
If the acid is a carboxylic acid, the compound contains a –COX functional group, which consists of a carbonyl group singly bonded to a halogen atom. Carboxylic acids are Organic acids characterized by the presence of a Carboxyl group, which has the formula -C(=OOH usually written -COOH or -CO2H In Organic chemistry, functional groups are specific groups of Atoms within Molecules that are responsible for the characteristic Chemical reactions In Organic chemistry, a carbonyl group is a Functional group composed of a Carbon Atom double-bonded to an Oxygen Abundance Owing to their high Reactivity, the halogens are found in the environment only in compounds or as Ions Halide ions and oxoanions The general formula for such an acyl halide can be written RCOX, where R may be, for example, an alkyl group, CO is the carbonyl group, and X represents the halogen atom, such as chlorine. An alkyl is a Univalent radical consisting of Carbon and Hydrogen atoms arranged in a chain Chlorine (ˈklɔriːn from the Greek word 'χλωρóς' ( khlôros, meaning 'pale green' is the Chemical element with Atomic number 17 and Acyl chlorides are the most commonly used acyl halides. In Organic chemistry, an acyl chloride (or acid chloride) is an Organic compound which is a reactive derivative of a Carboxylic acid.
The hydroxyl group of a sulfonic acid may also be replaced by a halogen to produce the corresponding sulfonyl halide. Sulfonic acid is an unstable Acid with the formula H-S(=O2-OH In practical terms this is almost always chlorine to create a sulfonyl chloride. Sulfonic acid is an unstable Acid with the formula H-S(=O2-OH
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Preparation
A common method for the synthesis of acyl halides in the laboratory is by reaction of carboxylic acids with reagents such as thionyl chloride or phosphorus pentachloride for acyl chlorides, phosphorus pentabromide for acyl bromides and cyanuric fluoride for acyl fluorides. Carboxylic acids are Organic acids characterized by the presence of a Carboxyl group, which has the formula -C(=OOH usually written -COOH or -CO2H Thionyl chloride (or thionyl dichloride) is an Inorganic compound with the formula S[[Oxygen O]] Cl 2 Phosphorus pentachloride is the Chemical compound with the formula PCl5 Phosphorus pentabromide is a reactive yellow solid of formula P[[Bromine Br]]5 which has the structure PBr4+ Br − A cyanogen halide is a molecule consisting of Cyanide and a Halogen.
Aromatic acyl chlorides can be prepared by chloroformylation, a specific type of Friedel-Crafts acylation using formaldehyde as the reagent. The Friedel-Crafts reactions are a set of reactions developed by Charles Friedel and James Crafts in 1877. Formaldehyde is a Chemical compound with the formula H2CO It is the simplest Aldehyde —an organic compound containing a terminal Carbonyl
Reactions
Acyl halides are rather reactive compounds often synthesized to be used as intermediates in the synthesis of other organic compounds. For example, an acyl halide can react with:
- water, to form a carboxylic acid
- an aromatic compound, using a Lewis acid catalyst such as AlCl3, to form an aromatic ketone. A chemical reaction is a process that always results in the interconversion of Chemical substances The substance or substances initially involved in a chemical reaction are called Water ( H2[[oxygen O]] H OH) is the most abundant Molecule on Earth 's surface composing of about 70% of the Earth's surface as Carboxylic acids are Organic acids characterized by the presence of a Carboxyl group, which has the formula -C(=OOH usually written -COOH or -CO2H In Chemistry, an alcohol is any Organic compound in which a Hydroxyl group ( - O[[hydrogen H]]) is bound to a Carbon Esters are a class of Chemical compounds and Functional groups Esters consist of an inorganic or organic Acid in which at least Amines are Organic compounds and Functional groups that contain a basic Nitrogen Atom with a Lone pair. In Chemistry, an amide is one of three kinds of Compounds (sometimes called acid amide the organic Functional group characterized A ketone (pronounced as key tone) is either the Functional group characterized by a Carbonyl group (O=C linked to two other Carbon atoms or See Friedel-Crafts acylation. The Friedel-Crafts reactions are a set of reactions developed by Charles Friedel and James Crafts in 1877.
In the above reactions, HX (hydrogen halide or hydrohalic acid) is also formed. Hydrogen halides (or hydrohalic acids) are acids resulting from the chemical reaction of Hydrogen with one of the Halogen elements ( Fluorine, For example, if the acyl halide is an acyl chloride, HCl (hydrogen chloride or hydrochloric acid) is also formed. Hydrochloric acid is the Solution of Hydrogen chloride ( H[[Chlorine Cl]] in water
Multiple functional groups
A molecule can have more than one acyl halide functional group. For example, "adipoyl dichloride", usually simply called adipoyl chloride, has two acyl chloride functional groups; see the structure at right. Adipoyl chloride (or adipoyl dichloride) is a di- Acyl chloride, with formula C6H8Cl2O2 In Organic chemistry, functional groups are specific groups of Atoms within Molecules that are responsible for the characteristic Chemical reactions It is the dichloride (i. e. , double chloride) of the 6-carbon dicarboxylic acid adipic acid. Adipic acid ( IUPAC Systematic name: hexanedioic acid) is a di Carboxylic acid. An important use of adipoyl chloride is polymerization with an organic di-amino compound to form a polyamide called nylon or polymerization with certain other organic compounds to form polyesters. In Polymer chemistry, polymerization is a process of reacting Monomer Molecules together in a Chemical reaction to form three-dimensional networks Overview Nylon is a Thermoplastic silky material first used commercially in a nylon- Bristled Toothbrush (1938 followed more famously by Polyester is a category of Polymers which contain the Ester Functional group in their main chain
Phosgene (carbonyl dichloride, Cl–CO–Cl) is a very toxic gas which may be thought of as the dichloride of carbonic acid (HO–CO–OH). Phosgene is the Chemical compound with the formula COCl2 This colorless gas gained infamy as a Chemical weapon during World War I Carbonic acid (ancient name acid of air or aerial acid) has the formula H2CO3 Both chloride radicals in phosgene can undergo reactions analogous to the preceding reactions of acyl halides. Phosgene is used a reactant in the production of polycarbonate polymers, among other industrial applications.
General hazards
Volatile acyl halides are lachrymatory because they can react with water at the surface of the eye producing hydrohalic and organic acids irritating to the eye. A lachrymatory agent or lachrymator (from lacrima meaning "a tear " in Latin) (commonly referred to as tear gas) is a Similar problems can result if one inhales acyl halide vapors. In general, acyl halides (even non-volatile compounds such as tosyl chloride) are irritants to the eyes, skin and mucous membranes. A tosyl group (abbreviated Ts or Tos) combines the Toluene and Sulfonyl Functional groups. The mucous membranes (or mucosae; singular mucosa) are linings of mostly endodermal origin covered in Epithelium, which are involved in
References
- ^ International Union of Pure and Applied Chemistry. The International Union of Pure and Applied Chemistry ( IUPAC) (aɪjuːpæk or ay-yoo-pec) is an international Non-governmental organization "acyl halides". Compendium of Chemical Terminology Internet edition. Compendium of Chemical Terminology (ISBN 0-86542-684-8 is a book published by IUPAC containing internationally accepted definitions for terms in Chemistry.
Dictionary
acyl halide
-noun
- (organic chemistry) Any organic compound containing an acyl functional group directly attached to a halogen.
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