Sulfonyl group

Short description: Chemical group (>S(=O)2)

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

## Contents

* 1 Group
* 2 Examples of sulfonyl group substituents
* 3 See also
* 4 References

## 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 (LiAlH
4) 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

* Fluorosulfonyl azide
* Sulfonyl halide
* Sulfonamide
* Sulfonate
* Methylsulfonylmethane (MSM)

## References

1. ↑ 1.0 1.1 1.2 1.3 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.

* v
* t
* e

Functional groups

| Only carbon,
hydrogen,
and oxygen|

| Hydrocarbons|

* Allene
* Alkene (Allyl group

|

Other|

* Acetoxy
* Acetyl
* Acryloyl
* Acyl
* Aldehyde
* Alkoxy (Methoxy)
* Benzoyl
* Carbonyl
* Carboxyl
* Carboxylic anhydride
* Dioxirane
* Epoxide
* Ester
* Ether
* Ethylenedioxy
* Hydroxy
* Ketone
* Methylenedioxy
* Peroxide (Organic)
* Ynone

Only one
element
apart from
C, H, O|

| Nitrogen|

* Amine
* Azo compound
* Cyanate
* Hydrazone
* Imide
* Imine
* Isocyanate
* Isonitrile
* Nitrene
* Nitrile
* Nitro compound
* Nitroso compound
* Organic amide
* Oxime

|

Phosphorus|

* Phosphonate
* Phosphonous

Sulfur|

* Disulfide
* Sulfone
* Sulfonic acid
* Sulfoxide
* Thial
* Thioester
* Thioether
* Thioketone
* Thiol

Selenium|

* Selenol
* Selenonic acid
* Seleninic acid
* Selenenic acid
* Selone

Tellurium|

* Tellurol
* Telluroketone

Other|

* Isothiocyanate
* Phosphoramide
* Sulfenyl chloride
* Sulfonamide
* Thiocyanate

See also chemical classification, chemical nomenclature ([[Chemistry:IUPAC nomenclature of inorganic, IUPAC nomenclature of organic chemistry|organic]])

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