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Information about Sulfonation



Sulfonic acid is a hypothetical acid with formula H-S(=O)2-OH. This compound is a less stable tautomer of sulfurous acid HO-S(=O)-OH, so sulfonic acid converts rapidly when it is formed. Derived compounds which replace the sulfur-bonded hydrogen with organic groups are stable. These may then form salts or esters, called sulfonates.

Sulfonic acids

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Ball-and-stick model of methanesulfonic acid
Sulfonic acids are a class of organic acids with the general formula R-S(=O)2-OH, where R is usually a hydrocarbon side chain. Sulfonic acids are typically much stronger acids than their carboxylic equivalents, and have the unique tendency to bind to proteins and carbohydrates tightly; most "washable" dyes are sulfonic acids (or have the functional sulfonyl group in them) for this reason. They are also used as catalysts and intermediates for a number of different products. Sulfonic acid salts (sulfonates) are important as detergents, and the antibacterial sulfa drugs are also sulfonic acid derivatives. The simplest example is methanesulfonic acid, CH3SO2OH, which is a reagent regularly used in organic chemistry. p-Toluenesulfonic acid is also an important reagent.

Note that the sulfonic acids and sulfonates are analogous to carboxylic acids and carboxylates; in both cases, -C(=O)- is replaced by -S(=O)2-. Chemical properties are similar as well, although sulfonic acids are often even stronger acids than carboxylic acids, the hydrogen being easier to leave than in most compounds, and they readily form esters.

The sulfonic acid and sulfonate functional groups, -SO2OH and -SO2O-, are found in many chemical compounds, e.g. certain detergents and dyes as well as in strongly acidic cation exchange resins.

Sulfonic acid chlorides

Sulfonic acid chlorides are a class of organic compounds with the general formula R-SO2-Cl. These compounds react readily with alcohols to sulfonic esters. Important acid chlorides are tosyl chloride, brosyl chloride, nosyl chloride and mesyl chloride. One synthetic procedure to synthesize sulfonic acid chlorides is the Reed reaction.

Sulfonic esters

Sulfonic esters are a class of organic compounds with the general formula R-SO2-OR. Sulfonic esters are considered good leaving groups in nucleophilic aliphatic substitution.

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Functional group
Chemical class: Alcohol • Aldehyde • Alkane • Alkene • Alkyne • Amide • Amine • Azo compound • Benzene derivative • Carboxylic acid • Cyanate • Disulfide • Ester • Ether • Haloalkane • Imine • Isocyanide • Isocyanate • Ketone • Nitrile • Nitro compound • Nitroso compound • Peroxide • Phosphoric acid • Pyridine derivative • Sulfone • Sulfonic acid • Sulfoxide • Thioester • Thioether • Thiol
ACID (Atomicity, Consistency, Isolation, Durability) is a set of properties that guarantee that database transactions are processed reliably. In the context of databases, a single logical operation on the data is called a transaction.
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Tautomers are organic compounds that are interconvertible by a chemical reaction called tautomerization. As most commonly encountered, this reaction results in the formal migration of a hydrogen atom or proton, accompanied by a switch of a single bond and adjacent
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Sulfurous acid (or sulphurous acid in British spelling) is the chemical compound with the formula H2SO3 molecule. There is no evidence for sulfurous acid in solution, but the molecule has been detected in the gas phase.
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Salt is a mineral essential for animal life, composed primarily of sodium chloride. Salt for human consumption is produced in different forms: unrefined salt (such as sea salt), refined salt (table salt), and iodized salt.
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Esters are a class of chemical compounds and functional groups. Esters consist of an inorganic or organic acid in which at least one -OH (hydroxy) group is replaced by an -O-alkyl (alkoxy) group.
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A sulfonate ion is an ion that contains the -S(=O)2-O− functional group. The general formula is RSO2O−, where R is some organic group.
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An organic acid is an organic compound with acidic properties. The most common organic acids are the carboxylic acids whose acidity is associated with their carboxyl group -COOH. Sulfonic acids, containing the group OSO3H, are relatively stronger acids.
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hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. With relation to chemical terminology, aromatic hydrocarbons or arenes, alkanes, alkenes and alkyne-based compounds composed entirely of carbon or hydrogen are referred to as "Pure" hydrocarbons, whereas
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side chain in organic chemistry and biochemistry is a part of a molecule that is attached to a core structure. An R group is a generic label for a side chain which can be anything; however, it is typically stable and covalently linked to the adjoining atom.
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Carboxyl group or carboxy group -COOH or CO2H is a functional group present in amino acids and carboxylic acids. Its structure composed of one carbon atom attached to an oxygen atom by double bond and to a hydroxyl group by a single bond.
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Proteins are large organic compounds made of amino acids arranged in a linear chain and joined together by peptide bonds between the carboxyl and amino groups of adjacent amino acid residues.
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dye can generally be described as a colored substance that has an affinity to the substrate to which it is being applied. The dye is generally applied in an aqueous solution, and may require a mordant to improve the fastness of the dye on the fiber.
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A sulfonyl group is an organic radical or functional group obtained from a sulfonic acid by the removal of the hydroxyl group. Sulfonyl groups can be written as having the general formula R-S(=O)2-R', where there are two double bonds between the sulfur and oxygen.
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catalysis is the acceleration (increase in rate) of a chemical reaction by means of a substance called a catalyst, which is itself not consumed by the overall reaction.
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A sulfonate ion is an ion that contains the -S(=O)2-O− functional group. The general formula is RSO2O−, where R is some organic group.
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Detergent is a compound, or a mixture of compounds, intended to assist cleaning. The term is often used to differentiate between soap and other chemical surfactants used for cleaning purposes.
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There are several sulphonamide-based groups of drugs. The original antibacterial sulfonamides (sometimes called simply sulfa drugs) are synthetic antimicrobial agents that contain the sulfonamide group. Some sulfonamides are also devoid of antibacterial activity, e.g.
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A reactant or reagent is a substance consumed during a chemical reaction.[1] Solvents and catalysts, although they are involved in the reaction, are usually not referred to as reactants.
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Organic chemistry is a specific discipline within chemistry which involves the scientific study of the structure, properties, composition, reactions, and preparation (by synthesis or by other means) of chemical compounds consisting primarily of carbon and hydrogen, which may
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p-Toluenesulfonic acid (PTSA) is an organic compound with the formula CH3C6H4SO3H. TsOH, as it is abbreviated, is a white solid that is soluble in water, alcohols, and other polar organic solvents.
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Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the formula -C(=O)OH, usually written -COOH or -CO2H. [1] Carboxylic acids are Bronsted acids — they are proton donors.
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Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the formula -C(=O)OH, usually written -COOH or -CO2H. [1] Carboxylic acids are Bronsted acids — they are proton donors.
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In organic chemistry, functional groups (or moieties) are specific groups of atoms within molecules, that are responsible for the characteristic chemical reactions of those molecules.
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Detergent is a compound, or a mixture of compounds, intended to assist cleaning. The term is often used to differentiate between soap and other chemical surfactants used for cleaning purposes.
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dye can generally be described as a colored substance that has an affinity to the substrate to which it is being applied. The dye is generally applied in an aqueous solution, and may require a mordant to improve the fastness of the dye on the fiber.
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An ion exchange resin is an insoluble matrix (or support structure) normally in the form of small (1-2 mm diameter) beads, usually white or yellowish, fabricated from an organic polymer substrate.
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organic compounds]] An organic compound is any member of a large class of chemical compounds whose molecules contain carbon; for historical reasons discussed below, a few types of compounds such as carbonates, carbon oxides and cyanides, as well as elemental carbon are
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alcohol is any organic compound in which a hydroxyl group (-OH) is bound to a carbon atom of an alkyl or substituted alkyl group. The general formula for a simple acyclic alcohol is CnH2n+1OH.
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