Sulfonate

A sulfonate ion is an ion that contains the -S(=O)2-O functional group. The general formula is "R"SO2O, where "R" is some organic group. They are conjugate bases of sulfonic acids with formula "R"SO2OH.

Sulfonates, being weak bases, are good leaving groups in Sn1, Sn2, E1 and E2 reactions.

As is common, the same term is used for compounds containing this functional group, ionic salts, or similar covalent compounds, esters.

Examples

* Mesylate (methanesulfonate) ion, CH3SO2O
* Triflate (trifluoromethanesulfonate) ion, CF3SO2O
* Tosylate ("p"-toluenesulfonate) ion, CH3C6H4SO2O
* Besylate (benzenesulfonate) ion, C6H5SO2O

A classic organic reaction for the preparation of sulfonates is that of alkyl halides with sulfites such as sodium sulfite , first described by Adolph Strecker in 1868 (Strecker sulfite alkylation) ["Ueber eine neue Bildungsweise und die Constitution der Sulfosäuren" Annalen der Chemie und Pharmacie Volume 148, Issue 1 , Pages 90 - 96 (p 90-96) 1868 DOI|10.1002/jlac.18681480108]

See also

* Sulfate
* Sulfoxide
* Sulfonyl

The preceding terms apply to salts and esters as well as anions.

References


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Look at other dictionaries:

  • sulfonate — [sylfɔnat] n. m. ÉTYM. XXe; de sulfon(é). ❖ ♦ Chim. Sel ou ester d un composé sulfoné …   Encyclopédie Universelle

  • Sulfonate — Sulfonate,   Salze und Ester der Sulfonsäuren …   Universal-Lexikon

  • sulfonate — [sul′fə nāt΄] n. a salt or ester of a sulfonic acid vt. sulfonated, sulfonating to introduce the sulfonic group into (an aromatic hydrocarbon) by treating with sulfuric acid …   English World dictionary

  • Sulfonate — allgemeine Sulfonsäure, R ist ein organischer Rest. Sulfonsäuren sind organische Schwefelverbindungen mit der allgemeinen Struktur R–SO2–OH, wobei R ein organischer Rest ist. Ihre Salze und Ester mit der allgemeinen Struktur R–SO2–O–X heißen… …   Deutsch Wikipedia

  • Sulfonate — Structure typique d un groupe sulfonate. Un ion sulfonate est un ion contenant le groupe S(=O)2 O−. Sa formule générale est de type R SO2O−, où R est un groupe organique. Ils constituent les bases conjuguées des acides sulfoniques de formule… …   Wikipédia en Français

  • sulfonate — A salt or ester of sulfonic acid. * * * sul·fo·nate or chiefly Brit sul·pho·nate səl fə .nāt n a salt or ester of a sulfonic acid sulfonate or chiefly Brit sulphonate vt, sul·fo·nat·ed or chiefly Brit sul·pho·nat·ed; sul·fo·nat·ing or chiefly… …   Medical dictionary

  • sulfonate — sulfonatas statusas T sritis chemija formulė RSO₃(M,R) atitikmenys: angl. sulfonate rus. сульфонат …   Chemijos terminų aiškinamasis žodynas

  • sulfonate — I. noun Date: 1876 a salt or ester of a sulfonic acid II. transitive verb ( nated; nating) Date: 1882 to introduce the SO3H group into; broadly to treat (an organic substance) with sulfuric acid • sulfonation noun …   New Collegiate Dictionary

  • sulfonate — /sul feuh nayt /, n., v., sulfonated, sulfonating. Chem. n. 1. an ester or salt derived from a sulfonic acid. v.t. 2. to make into a sulfonic acid, as by treating an aromatic hydrocarbon with concentrated sulfuric acid. 3. to introduce the… …   Universalium

  • sulfonate — 1. noun Any salt or ester of a sulfonic acid. 2. verb To treat or react with a sulfonic acid, or to introduce such a group into a compound …   Wiktionary

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