A sulfoxide is a chemical compound containing a sulfinyl functional group attached to two carbon atoms. A chemical compound is a substance consisting of two or more different elements chemically bonded together in a fixed proportion by Mass. In Organic chemistry, functional groups are specific groups of Atoms within Molecules that are responsible for the characteristic Chemical reactions Sulfoxides can be considered as oxidized sulfides. A thioether (similar to Sulfide) is a functional group in Organic chemistry that has the structure R1-S-R2 as shown on right (The use of the alternative spelling sulphoxide is discouraged by IUPAC. The International Union of Pure and Applied Chemistry ( IUPAC) (aɪjuːpæk or ay-yoo-pec) is an international Non-governmental organization ) An example of a sulfoxide occurring in nature is alliin. Alliin (al'-ee-in is a Sulfoxide that is a natural constituent of fresh Garlic.

Contents 1 Nature of the bond 2 Reactions 3 References 4 External links

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 and oxygen atoms differs from the conventional double bond between carbon and oxygen in, say, ketones. Sulfur or sulphur (ˈsʌlfɚ see spelling below) is the Chemical element that has the Atomic number 16 Oxygen (from the Greek roots ὀξύς (oxys (acid literally "sharp" from the taste of acids and -γενής (-genēs (producer literally begetteris the The S-O interaction has an electrostatic aspect, resulting in significant dipolar character, with negative charge centered on oxygen. Electrostatics is the branch of Science that deals with the Phenomena arising from what seems to be stationary Electric charges Since Classical The bond dipole moment uses the idea of Electric dipole moment to measure the polarity of a chemical bond within a Molecule. The bonding is similar to that in tertiary phosphine oxides, R₃P=O.

A lone pair of electrons resides on the sulfur atom giving it tetrahedral molecular geometry as for sp³ carbon. 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 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. When the two organic residues are dissimilar, the sulfur is a chiral center, for example, methylphenylsulfoxide. The term chiral (pronounced /ˈkaɪɹ(əl̩/ is used to describe an object that is non- superimposable on its mirror image

The energy required to invert this stereocenter is sufficiently high that sulfoxides are optically stable, that is, the rate of racemization is slow at room temperature. A stereocenter, or stereogenic centre, is any Atom in a Molecule bearing groups such that an interchanging of any two groups leads to a Stereoisomer In Chemistry racemization refers to partial conversion of one Enantiomer into another Chiral sulfoxides find application in certain drugs such as esomeprazole and Armodafinil, and they are also employed as chiral auxiliaries. Armodafinil ( Nuvigil) is a Stimulant -like drug produced by the Pharmaceutical company Cephalon Inc 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 ^[1] Many chiral sulfoxides are prepared from asymmetric catalytic oxidation of achiral sulfides with a transition metal and a chiral ligand. Asymmetric catalytic oxidation is a technique of oxidizing various substrates to give an Enantiopure product using a Catalyst. In Chemistry, the term transition metal (sometimes also called a transition element) has two possible meanings It commonly refers to any element in

Reactions

Sulfides are the usual starting materials to sulfoxides by organic oxidation. The term sulfide ( sulphide in British English) refers to several types of Chemical compounds containing Sulfur in its lowest Oxidation Organic reductions or organic oxidations or organic redox reactions are Redox reactions that take place with Organic compounds In Organic For example, dimethyl sulfide with oxidation state of -2 is oxidized to dimethyl sulfoxide with oxidation state 0. Dimethyl sulfide (DMS or methylthiomethane is an organosulfur compound with the formula (CH32S In Chemistry, the oxidation state is an indicator of the degree of Oxidation of an Atom in a Chemical compound. Dimethyl sulfoxide (DMSO is the Chemical compound with the formula (CH32SO Further oxidation converts the compound to dimethyl sulfone wherein sulfur has the oxidation state +2. Methylsulfonylmethane (MSM or dimethylsulfone is an Organosulfur compound with the formula (CH32SO2

Sulfoxides, such as DMSO, have basic character, being are excellent ligands and readily alkylated. Dimethyl sulfoxide (DMSO is the Chemical compound with the formula (CH32SO In Chemistry, a ligand is either an Atom, Ion, or Molecule (see also Functional group) that bonds to a central metal generally Alkyl sulfoxides are susceptible to deprotonation by strong bases, such as sodium hydride. Sodium hydride is the Chemical compound with the formula NaH It is primarily used as a strong base in Organic synthesis. ^[2]

References

External links

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