Sulfonate

From Wikipedia, the free encyclopedia

The structure of a typical sulfonate group.
The structure of a typical sulfonate group.

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. They are conjugate bases of sulfonic acids with formula RSO2OH.

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.

[edit] 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)[1]

[edit] See also

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

[edit] References

  1. ^ 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