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As mentioned earlier, the requirement for an atom to be a chirality center is that the atom must be sp hybridized with four different attachments. Because of this, all chirality centers are stereocenters. However, only under some conditions is the reverse true. Recall that a point can be considered a
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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
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of molecules containing the same composition and connectivity (bonding); the molecules must have multiple (two or more) stereocenters to be classified as enantiomers or diastereomers. Enantiomers and diastereomers will produce individual stereoisomers that contribute to the total number of possible
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on its mirror image; the presence of a meso compound will reduce the number of possible stereoisomers. Since a meso compound is superposable on its mirror image, the two "stereoisomers" are actually identical. Resultantly, a meso compound will reduce the number of stereoisomers to below the
420:(CIP) system uses R and S designations to define the configuration of atoms about any stereocenter. A designation of R denotes a clockwise direction of substituent priority around the stereocenter, while a designation of S denotes a counter-clockwise direction of substituent priority.
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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
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Stereocenters are important identifiers for chiral or achiral molecules. As a general rule, if a molecule has no stereocenters, it is considered achiral. If it has at least one stereocenter, the molecule has the potential for chirality. However, there are some exceptions like
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Chirality is not limited to carbon atoms, though carbon atoms are often centers of chirality due to their ubiquity in organic chemistry. Nitrogen and phosphorus atoms can also form bonds in a tetrahedral configuration. A nitrogen in an
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geometries may also be chiral due to having different ligands. For the octahedral case, several chiralities are possible. Having three ligands of two types, the ligands may be lined up along the meridian, giving the
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are a type of stereocenter with four different substituent groups; chirality centers are a specific subset of stereocenters because they can only have sp hybridization, meaning that they can only have
471:(a carbon atom bonded to four different entities) to a broader definition of any atom with four different attachment groups in which an interchanging of any two attachment groups gives rise to an
436:(atoms or groups of atoms) in a spatial arrangement which is non-superposable on its mirror image. Chirality centers must be sp hybridized, meaning that a chirality center can only have
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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
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sterocenter with a minimum of three attachment points; stereocenters can be either sp or sp hybridized, as long as the interchanging any two different groups creates a new
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is the number of tetrahedral stereocenters. However, this is an upper bound because molecules with symmetry frequently have fewer stereoisomers.
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molecules; stereocenters can contain single bonds or double bonds. The number of hypothetical stereoisomers can be predicted by using 2, with
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isomer. Having three bidentate ligands of only one type gives a propeller-type structure, with two different enantiomers denoted Λ and Δ.
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Smith, Janice
Gorzynski (2011). "Chapter 25 Amines". In Hodge, Tami; Nemmers, Donna; Klein, Jayne (eds.).
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atom, though it is also possible for other atoms to be chirality centers, especially in areas of
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with chiral centers may not exhibit chirality due to the presence of a two-fold rotation axis.
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double bond. Since stereocenters can exist on achiral molecules, stereocenters can have either
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The stereoisomers produced by the presence of multiple stereocenters can be defined as
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A carbon atom that is attached to four different substituent groups is called an
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Configuration is defined as the arrangement of atoms around a stereocenter. The
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may also provide for chirality without having an actual chiral center present.
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may be a stereocenter if all three groups attached are different because the
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Brown, William; Iverson, Brent; Anslyn, Eric; Foote, Christopher (2018).
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Mislow, Kurt; Siegel, Jay (1984). "Stereoisomerism and local chirality".
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at that nitrogen are present under normal circumstances. Racemization by
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that make molecules with multiple stereocenters considered achiral.
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provides insufficient context for those unfamiliar with the subject
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The concept of a chirality center generalizes the concept of an
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872:(3rd ed.). New York, NY: McGraw-Hill. pp. 949–993.
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cations), or slow, which allows the existence of chirality.
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Additionally, certain configurations may not exist due to
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Atom which is the focus of stereoisomerism in a molecule
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691:"Organic Chemistry with a Biological Emphasis Volume I"
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However, the stereoisomers produced may also give a
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510:of the amine functions as a fourth group. However,
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103:. Unsourced material may be challenged and removed.
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1051:Ultraviolet–visible spectroscopy of stereoisomers
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585:Chirality (chemistry) § Stereogenic centers
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781:"Grasping the Concepts of Stereochemistry"
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218:Learn how and when to remove this message
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288:. Stereocenters are also referred to as
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720:. December 15, 2021
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516:pyramidal inversion
462:inorganic chemistry
290:stereogenic centers
260:at the stereocenter
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697:: 170, 177.
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370:enantiomers
359:tetrahedral
309:tetrahedral
254:enantiomers
993:Enantiomer
602:References
543:octahedral
473:enantiomer
450:phosphorus
258:amino acid
123:newspapers
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936:Chirality
814:0021-9584
792:(1): 20.
518:, causes
400:reasons.
208:June 2021
58:talk page
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524:epimers
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341:achiral
301:achiral
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