Enantiomers vs. Diastereomers — What's the Difference?
By Tayyaba Rehman — Published on November 13, 2023
Enantiomers are mirror-image isomers that aren't superimposable, while Diastereomers are stereoisomers that aren't mirror images.
Difference Between Enantiomers and Diastereomers
Table of Contents
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Key Differences
Enantiomers are a type of stereoisomer that are non-superimposable mirror images of each other. Think of them like left and right hands. In contrast, Diastereomers are stereoisomers that aren't mirror images.
In the world of Enantiomers, if one isomer rotates plane-polarized light to the right (dextrorotatory), its mirror image will rotate light to the left (levorotatory). However, Diastereomers don't necessarily show such opposite optical behaviors.
Chirality is a property where a molecule cannot be superimposed on its mirror image, leading to Enantiomers. However, Diastereomers can arise when two or more stereoisomers of a compound have different configurations at one or more (but not all) of the equivalent (related) stereocenters.
Enantiomers always have the same physical properties (e.g., boiling point, melting point), but they differ in how they interact with plane-polarized light. Diastereomers, on the other hand, have different physical properties and different chemical reactivities.
A racemic mixture contains equal amounts of both Enantiomers and is optically inactive because the two enantiomers cancel out each other's optical activities. Diastereomers, since they are not mirror images, don't form racemic mixtures.
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Comparison Chart
Mirror Image
Yes, they are mirror images of each other.
No, they aren't mirror images.
Superimposability
Non-superimposable
Might or might not be superimposable
Physical Properties
Same
Different
Optical Activity
Opposite directions
Not necessarily opposite
Chemical Reactivity
Same
Different
Compare with Definitions
Enantiomers
Enantiomers are stereoisomers that are mirror images of each other.
The D and L forms of amino acids are Enantiomers.
Diastereomers
Diastereomers do not exhibit opposite optical activities like enantiomers.
Two Diastereomers might both rotate light to the right but at different angles.
Enantiomers
Enantiomers are isomers that are mirror reflections but can't be superimposed.
Like left and right hands, Enantiomers are similar yet distinct.
Diastereomers
Diastereomers are stereoisomers that aren't mirror images.
The alpha and beta forms of glucose are Diastereomers.
Enantiomers
Enantiomers are chiral molecules that rotate plane-polarized light in opposite directions.
The Enantiomers of limonene smell like oranges and lemons.
Diastereomers
Diastereomers have different physical properties and chemical reactivities.
Unlike Enantiomers, Diastereomers can have different melting points.
Enantiomers
Enantiomers have the same physical properties but differ in optical activity.
Two Enantiomers might melt at the same temperature, but they'll rotate light differently.
Diastereomers
Diastereomers are one of the two main types of stereoisomers.
In the realm of stereoisomerism, we encounter Enantiomers and Diastereomers as the primary classifications.
Enantiomers
Enantiomers are non-superimposable mirror-image molecules.
The two forms of the drug thalidomide are Enantiomers, where one form is therapeutic and the other is teratogenic.
Diastereomers
Diastereomers arise from different configurations at some stereocenters of a molecule.
In a molecule with multiple chiral centers, Diastereomers can form when not all centers are mirrored.
Enantiomers
Either of a pair of molecules that are mirror images but cannot be superimposed on each other, and that rotate the plane of polarized light by an equal amount in opposite directions. Also called enantiomorph, optical isomer.
Diastereomers
Plural of diastereomer
Enantiomers
Plural of enantiomer
Common Curiosities
How do Enantiomers differ from Diastereomers?
Enantiomers are mirror images, while Diastereomers aren't.
Is a racemic mixture related to Enantiomers?
Yes, it's a 1:1 mixture of two Enantiomers.
Can Diastereomers have different melting points?
Yes, they can have different physical properties.
How can one differentiate between Enantiomers in a lab?
By their ability to rotate plane-polarized light in opposite directions.
How do Diastereomers arise?
They form from different configurations at some of the stereocenters in a molecule.
Can Diastereomers be chiral?
Yes, they can be chiral, but not always.
What are Enantiomers?
They're non-superimposable mirror-image molecules.
Do Enantiomers have the same boiling point?
Yes, they have the same physical properties.
What's the optical activity of Enantiomers?
They rotate plane-polarized light in opposite directions.
Are all stereoisomers either Enantiomers or Diastereomers?
Yes, these are the two primary classifications of stereoisomers.
Do Diastereomers form racemic mixtures?
No, they don't form racemic mixtures since they aren't mirror images.
How are Enantiomers and Diastereomers related to stereoisomerism?
They are the two main types of stereoisomers.
What's the significance of Enantiomers in drug development?
One enantiomer can be therapeutic while the other can be harmful.
Are Enantiomers chiral?
Yes, they're always chiral.
Why are Diastereomers important in organic chemistry?
They allow for the study of molecules with different physical properties and reactivities.
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Written by
Tayyaba RehmanTayyaba Rehman is a distinguished writer, currently serving as a primary contributor to askdifference.com. As a researcher in semantics and etymology, Tayyaba's passion for the complexity of languages and their distinctions has found a perfect home on the platform. Tayyaba delves into the intricacies of language, distinguishing between commonly confused words and phrases, thereby providing clarity for readers worldwide.
