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Concept
Diastereomer
Summary
In stereochemistry, diastereomers (sometimes called diastereoisomers) are a type of stereoisomer. Diastereomers are defined as non-mirror image, non-identical stereoisomers. Hence, they occur when two or more stereoisomers of a compound have different configurations at one or more (but not all) of the equivalent (related) stereocenters and are not mirror images of each other.
When two diastereoisomers differ from each other at only one stereocenter, they are epimers. Each stereocenter gives rise to two different configurations and thus typically increases the number of stereoisomers by a factor of two.
Diastereomers differ from enantiomers in that the latter are pairs of stereoisomers that differ in all stereocenters and are therefore mirror images of one another.
Enantiomers of a compound with more than one stereocenter are also diastereomers of the other stereoisomers of that compound that are not their mirror image (that is, excluding the opposing enantiomer).
Diastereomers have different physical properties (unlike most aspects of enantiomers) and often different chemical reactivity.
Diastereomers differ not only in physical properties but also in chemical reactivity — how a compound reacts with others. Glucose and galactose, for instance, are diastereomers. Even though they share the same molar weight, glucose is more stable than galactose. This difference in stability causes galactose to be absorbed slightly faster than glucose in human body.
Diastereoselectivity is the preference for the formation of one or more than one diastereomer over the other in an organic reaction. In general, stereoselectivity is attributed to torsional and steric interactions in the stereocenter resulting from electrophiles approaching the stereocenter in reaction.
When the single bond between the two centres is free to rotate, cis/trans descriptors become invalid. Two widely accepted prefixes used to distinguish diastereomers on sp3-hybridised bonds in an open-chain molecule are syn and anti.
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