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A Meso compound or meso isomer is a chemical compound with molecules that contain 2 or more asymmetric (chiral) centers but which is optically inactive (or achiral) because it contains an internal plane of symmetry. For example one of the isomers of tartaric acid is a meso compound:

If you rotate the molecule 180° you will have the same apparent stereochemistry. (The bottom must be rotated within the plane of your monitor.) Stereochemistry

For a compound with multiple asymmetric carbons, an internal plane of symmetry indicates that the compound is achiral. However, it is still possible for a compound with multiple asymmetric carbons and no internal plane of symmetry to be meso. If there is only one asymmetric carbon, then the compound must be chiral.

 

This article is licensed under the GNU Free Documentation License. It uses material from the "Meso compound".

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