Sulfoxide
2248699
220483087
2008-06-20T02:13:27Z
WuBot
7192839
robot Adding: [[pl:Sulfotlenki]]
[[Image:Sulfoxide.png|right|thumb|150px|Sulfinyl group]]
A '''sulfoxide''' is a [[chemical compound]] containing a '''sulfinyl''' [[functional group]] attached to two carbon atoms. Sulfoxides can be considered as oxidized [[thioether|sulfides]]. (The use of the alternative spelling '''sulphoxide''' is discouraged by [[IUPAC]].) An example of a sulfoxide occurring in nature is [[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]] and [[oxygen]] 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 [[Bond dipole moment|dipolar]] character, with negative charge centered on oxygen. The bonding is similar to that in tertiary phosphine oxides, R<sub>3</sub>P=O.
[[Image:Sulfoxide-resonance.png|300px|center|Sulfoxide group]]
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 [[chirality (chemistry)|chiral center]], for example, methylphenylsulfoxide.
[[Image:Sulfoxide-tetrahedral.png|135px|center]]
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 auxiliary|chiral auxiliaries]].<ref>''Oxidation of sulfides to chiral sulfoxides using Schiff base-vanadium (IV) complexes'' Ángeles Gama, Lucía Z. Flores-López, Gerardo Aguirre, Miguel Parra-Hake, Lars H. Hellberg, and Ratnasamy Somanathan [[Arkivoc]] MX-789E '''2003''' [http://www.arkat-usa.org/ark/journal/2003/I11_Mexico/MX-789E/789E.asp Online article]</ref> Many chiral sulfoxides are prepared from [[asymmetric catalytic oxidation]] of achiral sulfides with a [[transition metal]] and a chiral ligand.
==Reactions==
[[Sulfide]]s 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 [[Methylsulfonylmethane|dimethyl sulfone]] wherein sulfur has the oxidation state +2.
Sulfoxides, such as [[dimethyl sulfoxide|DMSO]], have basic character, being are excellent [[ligand]]s and readily alkylated. Alkyl sulfoxides are susceptible to deprotonation by strong bases, such as [[sodium hydride]].<ref>Iwai, I.; Ide, J. "2,3-Diphenyl-1,3-Butadiene" Organic Syntheses, Collected Volume 6, p.531 (1988). http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=CV6P0531.pdf.</ref>
==References==
<div class="references-small"><references/></div>
==External links==
*
{{Functional Groups}}
[[Category:Functional groups]]
[[Category:Organosulfur compounds]]
[[Category:Oxygen compounds]]
[[de:Sulfoxide]]
[[es:Sulfóxido]]
[[fr:Sulfoxide]]
[[mk:Сулфоксид]]
[[ja:スルホキシド]]
[[pl:Sulfotlenki]]
[[zh:亚砜]]