:Sulfonyl group
{{short description|1=Chemical group (>S(=O)₂)}}
{{confuse|Thiosulfonate|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.{{cite book | first1 = Michael B. | last1 = Smith | first2 = Jerry | last2 = March | title = March's Advanced Organic Chemistry | publisher = John Wiley & Sons | year = 2007 | edition=6th | isbn = 978-0-471-72091-1 }}{{rp|1470-1476}}
Group
Sulfonyl groups can be written as having the general formula {{chem2|R\sS(\dO)2\sR′}}, where there are two double bonds between the sulfur and oxygen.{{rp|53}}{{Clayden|pages=1249-1251}}
Sulfonyl groups can be reduced to the sulfide with diisobutylaluminium hydride (DIBALH). Lithium aluminium hydride ({{chem2|LiAlH4}}) reduces some but not all sulfones to sulfides.{{rp|1851}}
In inorganic chemistry, when the group {{chem2|\sS(\dO)2\s}} is not connected to any carbon atoms, it is referred to as sulfuryl.{{Greenwood&Earnshaw2nd|pages=694-695}}
Examples of sulfonyl group substituents
The names of sulfonyl groups typically end in -syl, such as:{{rp|497}}
:
| class=wikitable
!Group name !Full name !Example |
| Tosyl
|p-toluenesulfonyl |Ts |Tosyl chloride (p-toluenesulfonyl chloride) |
| Brosyl
|p-bromobenzenesulfonyl |Bs | |
| Nosyl
|o- or p-nitrobenzenesulfonyl |Ns | |
| Mesyl
|methanesulfonyl |Ms |Mesyl chloride (methanesulfonyl chloride) |
| Triflyl
|trifluoromethanesulfonyl |Tf | |
| Tresyl
|2,2,2-trifluoroethyl-1-sulfonyl | | |
| Dansyl
|5-(dimethylamino)naphthalene-1-sulfonyl |Ds |