Sulfonyl group

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

## Group

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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

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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

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

## References

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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\. doi:10.1016/C2009-0-30414-6. ISBN 978-0-08-037941-8.

* v
* t
* e

Functional groups

Hydrocarbons
(only C and H)|

* Alkyl
* Methyl
* Ethyl
* Propyl
* Cyclopropyl
* Butyl
* Pentyl
* Methylene
* Bridge
* Methine
* Alkene
* Vinyl
* Allyl
* 1-Propenyl
* Crotyl
* Allene
* Cumulene
* Aryl
* Phenyl
* Benzyl
* Alkyne
* Carbene

Only carbon,
hydrogen,
and oxygen
(only C, H and O)|

| R-O-R|

* Acetal
* Alcohol
* Alkoxy
* Methoxy
* Ether
* Enol ether
* Epoxide
* Peroxy
* Hydroperoxy
* Dioxiranes
* Ethylenedioxy
* Methylenedioxy

|

carbonyl|

* Acyl
* Acetyl
* Acryloyl
* Benzoyl
* Aldehyde
* Ketene
* Ketone
* Ynone
* Reductone

carboxy|

* Carboxyl
* Acetoxy
* Anhydride
* Ester
* Orthoester

Only one
element,
not being
carbon,
hydrogen,
or oxygen
(one element,
not C, H or O)|

| Nitrogen|

* Amine
* Enamine
* Ammonium
* Hydrazo
* Nitrene
* Imine
* Oxime
* Hydrazone
* Azo
* Amide
* Imidate
* Amidine
* Carbamate
* Imide
* Nitrile
* Isonitrile
* Cyanate
* Isocyanate
* Nitrate
* Nitrite
* Nitro
* Nitroso
* NONOate
* Triazole
* Tetrazole

|

Silicon|

* Silane
* Hydrosilane
* Chlorosilane
* Silene
* Silanol
* Siloxide
* Siloxane
* Silanone
* Silether
* Silole
* Silatrane
* Silicate

Phosphorus|

* Phosphate
* Phosphodiester
* Phosphonate
* Phosphite
* Phosphonous
* Phosphinate
* Phosphine oxide
* Phosphine
* Phosphonium
* Phosphaalkene
* Phosphaalkyne
* Phosphaallene

Sulfur|

* Thiol
* Thioether
* Sulfonium
* Thia-crown ether
* Persulfide
* Disulfide
* Sulfenic acid
* Thiosulfinate
* Sulfoxide
* Thiosulfonate
* Sulfinic acid
* Sulfone
* Sulfonic acid
* Thioketone
* Thial
* Thioester
* Thionoester
* Thioxanthate
* Xanthate

Boron|

* Boronic acid
* Borinic acid

Selenium|

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

Tellurium|

* Tellurol
* Telluroketone
* telluroether

Polonium|

* Polonol
* Polonoether

Halo|

* Haloalkane
* Fluoroethyl
* Trifluoromethyl
* Trichloromethyl
* Trifluoromethoxy
* Hypervalent iodine
* Vinyl halide
* Iodide
* Acyl halide
* Chloride
* Perchlorate

Other|

* Isothiocyanate
* Phosphoramides
* Sulfenyl chloride
* Sulfonamide
* Thiocyanate
* Sulfinylamines

See also
chemical classification
chemical nomenclature

inorganic
organic
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