Meso compound

A meso compound or meso isomer is a non-optically active member of a set

of stereoisomers, at least two of which are optically active.[1][2] This means that despite
containing two or more stereocenters (chiral centers) it is not chiral. A meso compound is
superimposable on its mirror image, and it does not produce a "(+)" or "(-)" reading when
analyzed with a polarimeter.[3]

For example, there are 3 isomers of tartaric acid (depicted below), there is a meso
compound (the 2R,3S and 2S,3R isomers are equivalent) and the optically active pair
of levotartaric acid (D-(S,S)-(−)-tartaric acid) and dextrotartaric acid (L-(R,R)-(+)-tartaric
acid). In the meso compound an internal plane of symmetry exists, bisecting the molecule
which is not present in the non-meso compounds. That is, on rotating the meso compound
by 180° on a plane perpendicular to the screen, the same stereochemistry is obtained,
again this is not seen in the non-meso tartaric acid. (see Fischer projection).[3]

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-pentanediol, both the second and fourth
carbons, which are stereocenters, have all four substituents in common.

Since a meso isomer has a superimposable mirror image, a compound with a total
of n stereocenters cannot have 2n stereoisomers if at least one of the stereoisomers is
meso.[4]

Metamerism
a form of isomerism, that property of certain compound bodies by which they have the
same chemical elements combined in the same proportion and with the same molecular
weight, while differingin chemical properties. Thus, aldehyde and ethylene oxid have
their elements in the same proportion, C2H4O, and the same molecular weight, 44, but are
very different in their chemical properties. Two metameric bodies do not, however,
belong to the same class or series of compounds.

Example:

Diastereomers (diastereoisomers) are stereoisomers that are notenantiomers.

[1]
Diastereomerism occurs 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.[2]When two
diastereoisomers differ from each other at only one stereocenter they are epimers. Each
stereocenter gives rise to two different configurations and thus to two different
stereoisomers.

Diastereomers differ from enantiomers in that the latter are pairs of stereoisomers which
differ in all stereocenters and are therefore mirror images of one another.[3] 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. Diastereomers have
different physical properties and different reactivity, unlike enantiomers.

Cis-trans isomerism and conformational isomerism are also forms of diastereomerism.

Diastereoselectivity is the preference for the formation of one or more than one
diastereomer over the other in an organic reaction.