Sulfonyl group

Not to be confused with Thiosulfonate or Sulfonate.
A sulfone. It consists of a sulfonyl group bonded with two organic substituents.

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 

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

References

  1. ^ a b c d Smith, Michael B.; March, Jerry (2007). March's Advanced Organic Chemistry (6th ed.). John Wiley & Sons. ISBN 978-0-471-72091-1.
  2. ^ Clayden, Jonathan; Greeves, Nick; Warren, Stuart; Wothers, Peter (2001). Organic Chemistry (1st ed.). Oxford University Press. pp. 1249–1251. ISBN 978-0-19-850346-0.
  3. ^ Greenwood, Norman N.; Earnshaw, Alan (1997). Chemistry of the Elements (2nd ed.). Butterworth-Heinemann. pp. 694–695. ISBN 978-0-08-037941-8.