Stereocenter

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A stereocenter in organic chemistry generally refers to a carbon atom in a chemical compound that has four different types of atoms or groups of atoms attached to it. This type of stereocenter is otherwise known as an asymmetric carbon atom or a chiral carbon.

Other atoms may also be stereocenters in inorganic chemistry or in carbon analogs.

Having four different groups to the carbon automatically means it has an hybridisation1 of sp3; thus, no carbon involved in a pi bond (double bond) with another atom can be a stereocenter.

Stereocenters are very important in organic chemistry and biochemistry. Do note that a compound can have just about as many stereocenters as it can get away with, which totals for 2n stereoisomers, where n is the number of stereocenters.

External links

1 Hybridization theory (flash movie)

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A stereocenter is an atom at which the interchange of two groups produces a stereoisomer. Therefore, both asymmetric carbons-where the interchange of two groups produces an enantiomer and the carbons where the interchange of two groups converts a cis isomer to a trans isomer are stereocenters.


Mr. L. G. Wade, Jr., has a different opinion in his textbook, "Organic Chemistry", (6th Ed., Pearson Prentice Hall, Upper Saddle River, NJ, 2006). On pp170-171, the author of that book classified sp2 carbon atoms as "stereocenters".