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The sulfonate ion. In organosulfur chemistry, a sulfonate is a salt, anion or ester of a sulfonic acid. Its formula is R−S(=O) 2 −O −, containing the functional group −S(=O) 2 −O −, where R is typically an organyl group, amino group or a halogen atom. Sulfonates are the conjugate bases of sulfonic acids.
General structure of a sulfonic acid with the functional group indicated in blue. In organic chemistry, sulfonic acid (or sulphonic acid) refers to a member of the class of organosulfur compounds with the general formula R−S(=O) 2 −OH, where R is an organic alkyl or aryl group and the S(=O) 2 (OH) group a sulfonyl hydroxide. [1]
In organic synthesis, PPTS is used as a weakly acidic catalyst, providing an organic soluble source of pyridinium (C 5 H 5 NH +) ions.For example, PPTS is used to deprotect silyl ethers or tetrahydropyranyl ethers when a substrate is unstable to stronger acid catalysts.
Benzenesulfonic acid (conjugate base benzenesulfonate) is an organosulfur compound with the formula C 6 H 6 O 3 S.It is the simplest aromatic sulfonic acid.It forms white deliquescent sheet crystals or a white waxy solid that is soluble in water and ethanol, slightly soluble in benzene and insoluble in nonpolar solvents like diethyl ether.
Methyl fluorosulfonate, also known as magic methyl, is the organic compound with the formula FSO 2 OCH 3.It is a colorless liquid that is used as a strong methylating agent in organic synthesis.
Many method have been developed for introducing sulfonate groups aside from direction sulfonation. A classic named reaction is the Piria reaction (Raffaele Piria, 1851) in which nitrobenzene is treated with a metal bisulfite forming an aminosulfonic acid as a result of combined nitro group reduction and sulfonation. [2] [5] [6] The Piria reaction
8-Anilinonaphthalene-1-sulfonic acid (ANS), also called 1-anilino-8-naphthalenesulfonate, is an organic compound containing both a sulfonic acid and an amine group. This compound is used as a fluorescent molecular probe. [1]
German chemist Hermann Kolbe discovered MSA between 1842 and 1845 and originally termed it methyl hyposulphuric acid. [4] [5] [6]The discovery stemmed from earlier work by Berzelius and Marcet in 1813, who treated carbon disulfide with moist chlorine and produced a compound they named "sulphite of chloride of carbon".