Sulfonyl group

Not to be confused with Thiosulfonate or Sulfonate.

In organosulfur chemistry, a sulfonyl group is either a functional group found primarily in sulfones, or a substituent obtained from a sulfonic acid by the removal of the hydroxyl group, similarly to acyl groups.^{[1]: 1470–1476}

A sulfone. It consists of a sulfonyl group bonded with two organic substituents.

Group

Sulfonyl groups can be written as having the general formula R−S(=O)₂−R′, where there are two double bonds between the sulfur and oxygen.^{[1]: 53 [2]}

Sulfonyl groups can be reduced to the sulfide with diisobutylaluminium hydride (DIBALH). Lithium aluminium hydride (LiAlH₄) reduces some but not all sulfones to sulfides.^[1]: 1851

In inorganic chemistry, when the group −S(=O)₂− is not connected to any carbon atoms, it is referred to as sulfuryl.^[3]

Examples of sulfonyl group substituents

The names of sulfonyl groups typically end in -syl, such as:^[1]: 497

Group name	Full name	Pseudoelement symbol	Example
Tosyl	p-toluenesulfonyl	Ts	Tosyl chloride (p-toluenesulfonyl chloride) CH3C6H4SO2Cl
Brosyl	p-bromobenzenesulfonyl	Bs
Nosyl	o- or p-nitrobenzenesulfonyl	Ns
Mesyl	methanesulfonyl	Ms	Mesyl chloride (methanesulfonyl chloride) CH3SO2Cl
Triflyl	trifluoromethanesulfonyl	Tf
Tresyl	2,2,2-trifluoroethyl-1-sulfonyl
Dansyl	5-(dimethylamino)naphthalene-1-sulfonyl	Ds	Dansyl chloride

See also

• Sulfonyl halide
• Sulfonamide
• Sulfonate
• Methylsulfonylmethane (MSM)