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A meso compound or meso isomer is an optically inactive member of a set of stereoisomers, at least two of which are optically active.1 This means that it contains two or more stereocenters but is achiral (it is superposable on its mirror image, and it does not produce a "+" or "-" reading in a polarimeter).
For example, one of the isomers of tartaric acid depicted below is a meso compound. An internal mirror plane exists bisecting the molecule; on rotating the molecule 180° on a plane perpendicular to the screen, the same stereochemistry is obtained. (see Fischer projection)
It is a requirement for two of the stereocenters in a meso compound to have at least two substituents in common (though having this characteristic does not necessarily mean that the compound is meso). For example, in 2,4-pentadiol, both the second and fourth carbons, which are stereocenters, have all four substituents in common.
Since a meso isomer has a superposable mirror image, a compound with a total of n stereocenters cannot have 2n stereoisomers if at least one of the stereoisomers is meso.2
References
- ^ The Meaning of Meso Addison Ault Vol. 85 No. 3 March 2008 • Journal of Chemical Education 441
- ^ Bruice, Paula. Organic Chemistry. 2007. Pearson Prentice Hall. Upper Saddle River NJ.
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