Sulfoxide
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A sulfoxide is a chemical compound containing a sulfinyl functional group attached to two carbon atoms. Sulfoxides can be considered as oxidized sulfides. (The use of the alternative name sulphoxide is discouraged by IUPAC.) An example of a sulfoxide occurring in nature is alliin.
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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. The S-O interaction has a electrostatic aspect, resulting in significant dipolar character, with negative charge centered on oxygen. 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. When the two organic residues are dissimilar, the sulfur is a chiral center, for example, methylphenylsulfoxide.
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. Chiral sulfoxides find application in certain drugs such as esomeprazole and Armodafinil, and they are also employed as chiral auxiliaries.[1] Many chiral sulfoxides are prepared from asymmetric catalytic oxidation of achiral sulfides with a transition metal and a chiral ligand.
Reactions
Sulfides are the usual starting materials to sulfoxides by organic oxidation. For example, dimethyl sulfide with oxidation state of -2 is oxidized to dimethyl sulfoxide with oxidation state 0. Further oxidation converts the compound to dimethyl sulfone wherein sulfur has the oxidation state +2.
Sulfoxides, such as DMSO, have basic character, being are excellent ligands and readily alkylated. Alkyl sulfoxides are susceptible to deprotonation by strong bases, such as sodium hydride.[1]
References
External links
Functional groups |
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| Chemical class: Alcohol • Aldehyde • Alkane • Alkene • Alkyne • Amide • Amine • Azo compound • Benzene derivative • Carboxylic acid • Cyanate • Disulfide • Ester • Ether • Haloalkane • Hydrazone • Imine • Isocyanide • Isocyanate • Ketone • Oxime • Nitrile • Nitro compound • Nitroso compound • Peroxide • Phosphoric acid • Pyridine derivative • Sulfone • Sulfonic acid • Sulfoxide • Thioester • Thioether • Thiol |
Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
