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Encyclopedia > Stereocenter

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. Organic chemistry is the part of chemistry concerned with the composition, structure, properties, reactions and synthesis of organic compounds. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Atomic mass 12. ... Properties In chemistry and physics, an atom (Greek άτομον meaning indivisible) is the smallest possible particle of a chemical element that retains its chemical properties. ... A chemical compound is a chemical substance formed from two or more elements, with a fixed ratio determining the composition. ...


Other atoms may also be stereocenters in inorganic chemistry or in carbon analogs. Inorganic chemistry is the branch of chemistry concerned with the properties and reactions of inorganic compounds. ... An analog is in chemistry a chemical closely related to another usually sharing the same nucleus. ...


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. four sp³ orbitals three sp² orbitals In chemistry, hybridisation is the mixing of atomic orbitals belonging to a same electron shell to form new orbitals suitable for the qualitative description of atomic bonding properties. ... Electron atomic and molecular orbitals, showing a Pi-bond at the bottom right of the picture In chemistry, pi bonds (π bonds) are bonds with a single nodal plane containing the line segment between the two atoms. ...


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)


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".


  Results from FactBites:
 
stereocenter | English | Dictionary & Translation by Babylon (115 words)
In general, a stereocenter, or stereogenic centre, is any atom bearing groups such that an interchanging of any two groups leads to a stereoisomer.
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.
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