Sulfoxide

A sulfoxide is a chemical compound containing a sulfinyl functional group Functional group

In organic chemistry [i] functional groups are specific groups of atom [i]s within molecule [i]s, that ...

attached to two carbon atoms. Sulfoxides are the thio equivalents of ketone Ketone

A ketone is either the functional group [i] characterized by a carbonyl [i] group linked to two other carbon [i] ...

s.

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Encyclopedia

A sulfoxide is a chemical compound containing a sulfinyl functional group Functional group

In organic chemistry [i] functional groups are specific groups of atom [i]s within molecule [i]s, that ...

attached to two carbon atoms. Sulfoxides are the thio equivalents of ketone Ketone

A ketone is either the functional group [i] characterized by a carbonyl [i] group linked to two other carbon [i]...

s.

Nature of the bond

The structural formula Structural formula

The structural formula of a chemical compound [i] is a graphical representation of the molecular structu ...

of a sulfoxide is generally represented as R-S-R' where R and R' are the organic groups. The bond between the sulfur Sulfur

Sulfur or sulphur is the chemical element [i] in the periodic table [i] that has the symbol S' ...

and oxygen Oxygen

Oxygen is a chemical element [i] with the chemical symbol O and atomic number [i] 8....

atoms is not a normal double bond , and it is believed that electrostatic interaction between a negatively charged oxygen and positively charged sulfur accounts for most of the bonding.

Not drawn is the electron lone pair on sulfur and the geometry around sulfur is actually tetrahedral Tetrahedral molecular geometry

[i] is located at the center with four [[substituent]...

as with carbon. When the two organic residues are dissimilar sulfoxides can be chiral. Chiral sulfoxides find application in certain drugs such as esomeprazole Esomeprazole

Esomeprazole is a proton pump inhibitor [i] used in the treatment of dyspepsia, peptic ulcer disease [i] ...

and they are also employed as chiral auxiliary . Many chiral sulfoxides are prepared from asymmetric Chiral synthesis

Chiral synthesis also called asymmetric synthesis or enantioselective synthesis is organic synthesis [i] ...

oxidation of achiral sulfides with a transition metal Transition metal

In chemistry [i], the term transition metal has two possible meanings:
...

and a chiral ligand.

Reactions

Sulfides are often the starting materials for sulfones by organic oxidation. For example, dimethyl sulfide Dimethyl sulfide

Dimethyl sulfide or methylthiomethane is a sulfur [i] containing organic [i] chemical ...

with oxidation state Oxidation state

In chemistry [i], the oxidation state is a measure of the degree of oxidation [i] of an atom [i] in a chemical compound [i] ...

of -2 is oxidized to dimethyl sulfoxide Dimethyl sulfoxide

Dimethyl sulfoxide|doi=10.2174/092986706775197917}}.
...

with oxidation state 0. Further oxidation takes the compound to dimethyl sulfone Methylsulfonylmethane

Methylsulfonylmethane is an organic [i] sulfur [i] compound [i] belon...

with oxidation state +2.

Methyl sulfoxides have an acidic character, because the sulfoxide group stabilizes the anion that results from loss of a methyl hydrogen.

References