Stereocenter

Two enantiomers of a generic amino acid at the stereocenter

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.[1][2] 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.[2][3] Stereocenters can exist on chiral or achiral molecules; stereocenters can contain single bonds or double bonds.[1] 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.[4]

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.[5]

  1. ^ a b "5.4: Stereogenic Centers". libretexts.org. April 24, 2015.
  2. ^ a b Mislow, Kurt; Siegel, Jay (1984). "Stereoisomerism and local chirality". Journal of the American Chemical Society. 106 (11): 3319. doi:10.1021/ja00323a043.
  3. ^ Solomons, T. W. Graham; Fryhle, Craig (2004). Organic Chemistry (8th ed.). John Wiley & Sons.[page needed]
  4. ^ Cite error: The named reference :3 was invoked but never defined (see the help page).
  5. ^ Cite error: The named reference :2 was invoked but never defined (see the help page).

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