Everything about Sulfonic Acid totally explained
Sulfonic acid is an unstable
acid with the formula H-S(=O)
2-OH. Sulfonic acid is the less stable
tautomer of
sulfurous acid HO-S(=O)-OH into which sulfonic acid converts rapidly. Derived compounds which replace the sulfur-bonded hydrogen with organic groups are stable. These may then form
salts or
esters, called
sulfonates.
Sulfonic acids
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 acids and their salts (
sulfonates) are used extensively in such diverse products like
detergents, antibacterial drugs
sulfa drugs, anion exchange resins (water purification) and dyes.
The simplest example is
methanesulfonic acid, CH
3SO
2OH, which is a
reagent regularly used in
organic chemistry.
p-Toluenesulfonic acid is also an important reagent.
Sulfonic acid chlorides
Sulfonic acid chlorides are a class of
organic compounds with the general formula R-SO
2-Cl. These compounds react readily with nucleophiles (like
alcohols,
amines etc.) If the nucleophile is an alcohol the product is a sulfonic ester, if it's an amine the product is a sulfonamide. Important sulfonic acid chlorides are
tosyl chloride,
brosyl chloride,
nosyl chloride and
mesyl chloride. One synthetic procedure to synthesize sulfonic acid chlorides is the
Reed reaction. Sulfonyl chloride is very prone to hydrolysis. An ice/water bath can be used to decrease this effect (Titus 1982 & Lefevre 1996).
Sulfonic esters
Sulfonic esters are a class of
organic compounds with the general formula R-SO
2-OR. Sulfonic esters such as
methyl triflate are considered good
leaving groups in
nucleophilic aliphatic substitution.
Further Information
Get more info on 'Sulfonic Acid'.
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