Sulfonate

Organosulfur compound of the form R–S(=O)2–O (charge –1)

In

oxidizing

, and colorless. Many useful compounds and even some biochemicals feature sulfonates.

Sulfonate salts

shampoos, toothpaste laundry detergent, dishwashing liquid, etc.

A classic preparation of sulfonates is the Strecker sulfite alkylation, in which an alkali sulfite salt displaces a halide, typically in the presence of an iodine catalyst:^[1]

${\displaystyle {\ce {RX + M2SO3 -> RSO3M + MX}}}$

An alternative is the condensation of a sulfonyl halide with an alcohol in pyridine:^[2]

${\displaystyle {\ce {ROH{}+R'SO2Cl\ {\overset {Pyr}{->}}\ ROSO2R'+HCl}}}$

Sulfonic esters

Esters with the general formula R¹SO₂OR² are called sulfonic esters. Individual members of the category are named analogously to

Cyclic sulfonic esters are called sultones.

Tisocromide is an example of a sultone.

Examples

• Mesylate (methanesulfonate), CH₃−SO−3
• Triflate (trifluoromethanesulfonate), CF₃−SO−3
• Ethanesulfonate
  (esilate, esylate), CH₃CH₂−SO−3
• Tosylate
  (p-toluenesulfonate), p-CH₃−C₆H₄−SO−3
• Benzenesulfonate (besylate), C₆H₅−SO−3
• Closilate (closylate, chlorobenzenesulfonate), Cl−C₆H₄−SO−3
• Camphorsulfonate
  (camsilate, camsylate), (C₁₀H₁₅O)−SO−3
• Pipsylate (p-iodobenzenesulfonate derivative), p-I−C₆R₄−SO−3, where R is any group.^[5]
• Nosylate
  (o- or p-nitrobenzenesulfonate), o- or p-O₂N−C₆H₄−SO−3

See also

• Sulfate
• Sulfoxide
• Sulfonyl

References