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Encyclopedia > Diastereomer

Diastereomers (or diastereoisomers) are stereoisomers that are not enantiomers (mirror images of each other). Diastereomers can have different physical properties and different reactivity. In another definition diastereomers are pairs of isomers that have opposite configurations at one or more of the chiral centers but are not mirror images of each other [1]. Stereoisomerism is the arrangement of atoms in molecules whose connectivity remains the same but their arrangement in space is different in each isomer. ... In chemistry, enantiomers are stereoisomers that are mirror images of each other. ...


In simple terms two stereoisomers are said to be diastereoisomers if they are not mirror images of each other and one or more stereogenic centres differ between the two stereoisomers. According to this same definition, geometric isomerism is a form of diastereomerism. In chemistry a stereogenic center is often mistaken for a chiral center. ... Cis-2-butene Trans-2-butene In chemistry, geometric isomerism or cis-trans isomerism is a form of stereoisomerism and describes the orientation of functional groups within the molecule. ...


If a molecule contains a single asymmetric carbon atom or stereocenter, it will have two mirror image forms. If a molecule contains two asymmetric carbons, there are up to 4 possible configurations, and they cannot all be mirror images of each other. The possibilities continue to multiply as there are more asymmetric centers in a molecule. In science, a molecule is a group of atoms in a definite arrangement held together by chemical bonds. ... 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 ἄτομος or átomos meaning indivisible) is the smallest particle still characterizing a chemical element. ... 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. ...


Tartaric acid contains two asymmetric centers, but two of the "isomers" are equivalent and are called a meso compound. This configuration is not optically active, while the remaining two isomers are D- and L- mirror images, i.e. enantiomers. The meso form is a diastereomer of the other forms. Tartaric acid or H2C4H4O6 is a white crystalline organic acid. ... Meso compound is a chemical compound whose molecules contain asymmetric centers but which is optically inactive due to overall symmetry. ... When polarized light is passed through a substance containing chiral molecules (or nonchiral molecules arranged asymmetrically), the direction of polarization can be changed. ...

Image:L-tartaric acid.png Image File history File links File history Legend: (cur) = this is the current file, (del) = delete this old version, (rev) = revert to this old version. ...

Image:D-tartaric acid.png Image:DL-tartaric acid.png

(natural) tartaric acid
L-(+)-tartaric acid
dextrotartaric acid Image File history File links File history Legend: (cur) = this is the current file, (del) = delete this old version, (rev) = revert to this old version. ... Image File history File links File history Legend: (cur) = this is the current file, (del) = delete this old version, (rev) = revert to this old version. ...

D-(-)-tartaric acid
levotartaric acid

mesotartaric acid

(1:1)
DL-tartaric acid
"racemic acid"

The families of 4, 5 and 6 carbon carbohydrates contain many diastereomers because of the large numbers of asymmetric centres in these molecules. Two common prefixes used to distinguish diastereomers are threo and erythro. When drawn in the Fischer projection the erythro isomer has two identical substituents on the same side and the threo isomer has them on opposite sites. Cis-trans isomerism and conformational isomerism are also forms of diastereomerism. Lactose is a disaccharide found in milk. ... Fischer projection of D-glucose In chemistry (particularly organic chemistry and biochemistry), a Fischer projection is a two-dimensional representation of a three-dimensional organic molecule by projection. ... Cis-2-butene Trans-2-butene In chemistry, geometric isomerism or cis-trans isomerism is a form of stereoisomerism and describes the orientation of functional groups at the ends of a bond around which no rotation is possible. ... Conformational isomerism is the phenomenon of molecules with the same structural formula but different conformations (conformers) of atoms about a rotating bond. ...


Diastereoselectivity is the preference for the formation of one or more than one diastereomer over the other in an organic reaction. Organic reactions are chemical reactions between organic compounds. ...


Applications

As stated, two enantiomers will have identical physical properties, while diastereomers will not. This knowledge is harnessed in chiral synthesis to separate a mixture of enantiomers. This is the principle behind chiral resolution. After preparing the diastereomers, they are separated by chromatography or recrystallization. The two optical isomers of bromochlorofluoromethane Chiral synthesis (also called asymmetric synthesis) is organic synthesis which preserves or introduces a desired chirality. ... Chiral resolution in chemistry is a process for the separation of racemic compounds into their enantiomers [1]. Two common methods are: Derivatization of racemic compounds with optically pure reagents forming pairs of diastereomers which can be separated by conventional techniques in physical chemistry. ... Pictured is a sophisticated gas chromatography system. ... Insulin crystals Recrystallization is an essentially physical process that has meanings in chemistry, metallurgy and geology. ...


References

  1. ^ Garrett, Grisham "Biochemistry" 2nd ed., 1999, p. 213

  Results from FactBites:
 
Diastereomer - Wikipedia, the free encyclopedia (240 words)
Diastereomers are stereoisomers that are not enantiomers, or mirror images of each other.
The families of 5-6 carbon carbohydrates contain many diastereomers because of the large numbers of asymmetric centers in these molecules.
Diastereoselectivity is the preference for the formation of one or more than one diastereomer over the other in an organic reaction.
  More results at FactBites »


 
 

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