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Concept
Stereocenter
Summary
In stereochemistry, a stereocenter of a molecule is an atom (center), axis or plane that is the focus of stereoisomerism; that is, when having at least three different groups bound to the stereocenter, interchanging any two different groups creates a new stereoisomer. Stereocenters are also referred to as stereogenic centers.
A stereocenter is geometrically defined as a point (location) in a molecule; a stereocenter is usually but not always a specific atom, often carbon. Stereocenters can exist on chiral or achiral molecules; stereocenters can contain single bonds or double bonds. The number of hypothetical stereoisomers can be predicted by using 2n, with n being the number of tetrahedral stereocenters; however, exceptions such as meso compounds can reduce the prediction to below the expected 2n.
Chirality centers are a type of stereocenter with four different substituent groups; chirality centers are a specific subset of stereocenters because they can only have sp3 hybridization, meaning that they can only have single bonds.
Stereocenters can exist on chiral or achiral molecules. They are defined as a location (point) within a molecule, rather than a particular atom, in which the interchanging of two groups creates a stereoisomer. A stereocenter can have either four different attachment groups, or three different attachment groups where one group is connected by a double bond. Since stereocenters can exist on achiral molecules, stereocenters can have either sp3 or sp2 hybridization.
Stereoisomers are compounds that are identical in composition and connectivity but have a different spatial arrangement of atoms around the central atom. A molecule having multiple stereocenters will produce many possible stereoisomers. In compounds whose stereoisomerism is due to tetrahedral (sp3) stereogenic centers, the total number of hypothetically possible stereoisomers will not exceed 2n, where n is the number of tetrahedral stereocenters. However, this is an upper bound because molecules with symmetry frequently have fewer stereoisomers.
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