ion is an ion that contains the -S(=O)2
-O− functional group
. The general formula is R
, where R
is some organic group. They are conjugate bases
of sulfonic acids
with formula R
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.
- 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)
The preceding terms apply to salts and esters as well as anions.