Stereocenter

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In general, a stereocenter, or stereogenic centre, is any atom bearing groups such that an interchanging of any two groups leads to a stereoisomer [1]. In organic chemistry this usually refers to a carbon atom. However, other atoms may also be stereocenters in inorganic chemistry or in carbon analogs. Having four different groups attached to one carbon necessarily means that it is a stereogenic center that has a hybridisation1 of sp3 and is a tetrahedral stereogenic carbon. This type of stereocenter is also known as an asymmetric carbon atom. Some sp2 carbons are trigonal planar stereogenic carbons (e.g. cis- and trans-1,2-dichloroethene).[1]

A molecule can have multiple stereocenters, giving it many stereoisomers. In compounds whose stereoisomerism is due to tetrahedral stereogenic centers, the total number of hypothetically possible stereoisomers will not exceed 2n, where n is the number of tetrahedral stereocenters. Molecules with symmetry frequently have fewer than the maximum possible number of stereoisomers.

[edit] References

  1. ^ a b Solomons & Fryhle. (2004). Organic Chemistry, 8th ed..

[edit] External links

1 Hybridisation theory (flash movie)

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