Sulfoxide

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Sulfoxide

A sulfoxide is a chemical compound

Chemical compound

A chemical compound is a Chemical substance consisting of two or more different chemical element Chemical bond together in a fixed mass ratio that can be split into simpler substances....
containing a sulfinyl functional group

Functional group

In organic chemistry, functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules....
attached to two carbon atoms. Sulfoxides can be considered as oxidized sulfides

Thioether

A thioether is a functional group in organic chemistry that has the structure R1-S-R2 as shown on right. Like many other sulfur-containing compounds, Volatile organic compound thioethers characteristically have foul odors....
. (The use of the alternative spelling sulphoxide is discouraged by IUPAC.) An example of a sulfoxide occurring in nature is alliin

Alliin

Alliin is a sulfoxide that is a natural constituent of fresh garlic. It is a derivative of the amino acid cysteine. When fresh garlic is chopped or crushed, the enzyme alliinase converts alliin into allicin which is primarily responsible for the aroma of fresh garlic....
.

oxides are generally represented with the structural formula R-S(=O)-R', where R and R' are organic groups.

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Encyclopedia

A sulfoxide is a chemical compound

Chemical compound

Functional group

Thioether

Alliin

Nature of the bond

Sulfoxides are generally represented with the structural formula R-S(=O)-R', where R and R' are organic groups. The bond between the sulfur

Sulfur

Sulfur or sulphur is the chemical element that has the atomic number 16. It is denoted with the symbol S. It is an abundant Valence non-metal....
and oxygen

Oxygen

Oxygen no O2 produced; 2) O2 produced, but absorbed in oceans & seabed rock; 3) O2 starts to gas out of the oceans, but is absorbed by land surfaces and formation of ozone layer; 4-5) O2 sinks filled and the gas accumulates]]...
atoms differs from the conventional double bond between carbon and oxygen in, say, ketones. The S-O interaction has an electrostatic aspect, resulting in significant dipolar

Bond dipole moment

The bond dipole moment uses the idea of electric dipole moment to measure the chemical polarity of a chemical bond within a molecule. The bond dipole ? is given by:...
character, with negative charge centered on oxygen. The bonding is similar to that in tertiary phosphine oxides, R₃P=O.

A lone pair

Lone pair

A lone pair is a valence electron pair without bonding or sharing with other atoms. They are found in the outermost electron shell of an atom, so lone pairs are a subset of a molecule's valence electrons....
of electrons resides on the sulfur atom giving it tetrahedral molecular geometry

Tetrahedral molecular geometry

In a Tetrahedral molecular geometry a central atom is located at the center with four substituents that are located at the corners of a tetrahedron....
as for sp³ carbon. When the two organic residues are dissimilar, the sulfur is a chiral center

Chirality (chemistry)

The term chiral is used to describe an object that is non-Superposition on its mirror image.Human hands are perhaps the most universally recognized example of chirality: The left hand is a non-superposable mirror image of the right hand; no matter how the two hands are oriented, it is impossible for all the major features of both hands...
, for example, methylphenylsulfoxide.

The energy required to invert this stereocenter

Stereocenter

A stereocenter, or stereogenic center, is any point, though not necessarily an atom, in a molecule bearing groups such that an interchanging of any two groups leads to a stereoisomer ....
is sufficiently high that sulfoxides are optically stable, that is, the rate of racemization

Racemization

In chemistry racemization refers to partial conversion of one enantiomer into another....
is slow at room temperature. Chiral sulfoxides find application in certain drugs such as esomeprazole

Esomeprazole

Esomeprazole is a proton pump inhibitor developed and marketed by AstraZeneca which is used in the treatment of dyspepsia, peptic ulcer , gastroesophageal reflux disease and Zollinger-Ellison syndrome....
and Armodafinil

Armodafinil

Armodafinil is a stimulant-like drug produced by the pharmaceutical company Cephalon, which was approved by the Food and Drug Administration on June 15, 2007....
, and they are also employed as chiral auxiliaries

Chiral auxiliary

A chiral auxiliary is a chemical compound or unit that is temporarily incorporated into an organic synthesis so that it can be carried out asymmetrically with the selective formation of one of two enantiomers...
. Many chiral sulfoxides are prepared from asymmetric catalytic oxidation

Asymmetric catalytic oxidation

Asymmetric catalytic oxidation is a technique of oxidation various substrate s to give an enantiopure product using a catalyst....
of achiral sulfides with a transition metal

Transition metal

In chemistry, the term transition metal has two possible meanings:*It commonly refers to any element in the d-block of the periodic table, including the group 12 element elements zinc, cadmium and Mercury ....
and a chiral ligand.

Reactions

Sulfide

The term sulfide refers to several types of chemical compounds containing sulfur in its lowest oxidation number of −2.Formally, "sulfide" is the dianion, S2−, which exists in strongly alkaline aqueous solutions formed from H2S or alkali metal salts such as Li2S, Na2S, and K2...
s are the usual starting materials to sulfoxides by organic oxidation. For example, dimethyl sulfide

Dimethyl sulfide

Dimethyl sulfide or methylthiomethane is an Organosulfur compounds compound with the formula 2S. Dimethyl sulfide is a water-insoluble flammable liquid that boils at 37?C and has a characteristic disagreeable odor....
with oxidation state

Oxidation state

In chemistry, the oxidation state is an indicator of the degree of oxidation of an atom in a chemical compound. The formal oxidation state is the hypothetical Electrical charge that an atom would have if all bonds to atoms of different elements were 100% Ionic bond....
of -2 is oxidized to dimethyl sulfoxide

Dimethyl sulfoxide

Dimethyl sulfoxide is the chemical compound with the chemical formula 2SO. It was first synthesized in 1866 by the Russian scientist Alexander Saytzeff, who reported his findings in a German chemistry journal in 1867....
with oxidation state 0. Further oxidation converts the compound to dimethyl sulfone

Methylsulfonylmethane

Methylsulfonylmethane , also known as dimethyl sulfone, is an organosulfur compound with the chemical formula 2SO2. This colourless solid features the sulfone functional group and is considered relatively inert chemically....
wherein sulfur has the oxidation state +2.

Sulfoxides, such as DMSO

Dimethyl sulfoxide

Ligand

In chemistry, a ligand is either an atom, ion, or molecule that bonds to a central metal, generally involving formal donation of one or more of its electrons....
s and readily alkylated. Alkyl sulfoxides are susceptible to deprotonation by strong bases, such as sodium hydride

Sodium hydride

Sodium hydride is the chemical compound with the formula NaH. It is primarily used as a strong base in organic synthesis. NaH is representative of the saline hydrides, meaning it is a salt-like hydride, composed of Na+ and H- ions, in contrast to the more molecular hydrides such as borane, methane, ammonia and water....
.

Sulfoxide

Nature of the bond

Reactions

External links