A meso compound or meso isomer is a non-optically active member of a set of
stereoisomers
In stereochemistry, stereoisomerism, or spatial isomerism, is a form of isomerism in which molecules have the same molecular formula and sequence of bonded atoms (constitution), but differ in the three-dimensional orientations of their atoms in ...
, at least two of which are optically active. This means that despite containing two or more
stereocenter
In stereochemistry, a stereocenter of a molecule is an atom (center), axis or plane that is the focus of stereoisomerism; that is, when having at least three different groups bound to the stereocenter, interchanging any two different groups cr ...
s, the molecule is not chiral. A meso compound is "superposable" on its mirror image (not to be confused with superimposable, as any two objects can be superimposed over one another regardless of whether they are the same). Two objects can be superposed if all aspects of the objects coincide and it does not produce a "(+)" or "(-)" reading when analyzed with a
polarimeter
A polarimeter is a scientific instrument used to measure the angle of rotation caused by passing polarized light through an optically active substance. The name is derived from the Greek ''mésos'' meaning “middle”.
For example,
tartaric acid
Tartaric acid is a white, crystalline organic acid that occurs naturally in many fruits, most notably in grapes, but also in bananas, tamarinds, and citrus. Its salt, potassium bitartrate, commonly known as cream of tartar, develops naturally i ...
can exist as any of three stereoisomers depicted below in a
Fischer projection
In chemistry, the Fischer projection, devised by Emil Fischer in 1891, is a two-dimensional representation of a three-dimensional organic molecule by projection. Fischer projections were originally proposed for the depiction of carbohydrates an ...
. Of the four colored pictures at the top of the
diagram
A diagram is a symbolic representation of information using visualization techniques. Diagrams have been used since prehistoric times on walls of caves, but became more prevalent during the Enlightenment. Sometimes, the technique uses a three- ...
, the first two represent the meso compound (the 2'' R'',3'' S'' and 2'' S'',3'' R'' isomers are equivalent), followed by the optically active pair of levotartaric acid (L-(''R,R'')-(+)-tartaric acid) and dextrotartaric acid (D-(''S,S'')-(-)-tartaric acid). The meso compound is bisected by an internal
plane of symmetry
In mathematics, reflection symmetry, line symmetry, mirror symmetry, or mirror-image symmetry is symmetry with respect to a reflection. That is, a figure which does not change upon undergoing a reflection has reflectional symmetry.
In 2D ther ...
that is not present for the non-meso isomers (indicated by an X). That is, on reflecting the meso compound through a mirror plane perpendicular to the screen, the same stereochemistry is obtained; this is not the case for the non-meso tartaric acid, which generates the other
enantiomer
In chemistry, an enantiomer ( /ɪˈnænti.əmər, ɛ-, -oʊ-/ ''ih-NAN-tee-ə-mər''; from Ancient Greek ἐνάντιος ''(enántios)'' 'opposite', and μέρος ''(méros)'' 'part') – also called optical isomer, antipode, or optical ant ...
. The ''meso'' compound must not be confused with a 50:50
racemic
In chemistry, a racemic mixture, or racemate (), is one that has equal amounts of left- and right-handed enantiomers of a chiral molecule or salt. Racemic mixtures are rare in nature, but many compounds are produced industrially as racemates. ...
mixture of the two optically-active compounds, although neither will rotate light in a
inversion
Inversion or inversions may refer to:
Arts
* , a French gay magazine (1924/1925)
* ''Inversion'' (artwork), a 2005 temporary sculpture in Houston, Texas
* Inversion (music), a term with various meanings in music theory and musical set theory
* ...
or a rotoreflexion symmetry such as S. For example, there are two meso isomers of 1,4-difluoro-2,5-dichlorocyclohexane but neither has a mirror plane, and there are two meso isomers of 1,2,3,4-tetrafluorospiropentane (see figure). In fact, a meso compound may have no symmetry in some conformations, for instance, ''meso''
tartaric acid
Tartaric acid is a white, crystalline organic acid that occurs naturally in many fruits, most notably in grapes, but also in bananas, tamarinds, and citrus. Its salt, potassium bitartrate, commonly known as cream of tartar, develops naturally i ...
in its
gauche conformation
In chemistry, conformational isomerism is a form of stereoisomerism in which the isomers can be interconverted just by rotations about formally single bonds (refer to figure on single bond rotation). While any two arrangements of atoms in a molec ...
. A molecule with no symmetry is chiral. But the presence of equal quantities of the right-handed and left-handed conformations will mean that the mixture will not rotate polarized light.
Cyclic meso compounds
1,2-substituted
cyclopropane
Cyclopropane is the cycloalkane with the molecular formula (CH2)3, consisting of three methylene groups (CH2) linked to each other to form a ring. The small size of the ring creates substantial ring strain in the structure. Cyclopropane itself ...
has a meso
cis
Cis or cis- may refer to:
Places
* Cis, Trentino, in Italy
* In Poland:
** Cis, Świętokrzyskie Voivodeship, south-central
** Cis, Warmian-Masurian Voivodeship, north
Math, science and biology
* cis (mathematics) (cis(''θ'')), a trigonome ...
-isomer (molecule has a mirror plane) and two
trans
Trans- is a Latin prefix meaning "across", "beyond", or "on the other side of".
Used alone, trans may refer to:
Arts, entertainment, and media
* Trans (festival), a former festival in Belfast, Northern Ireland, United Kingdom
* ''Trans'' (film ...
-enantiomers:
The two cis stereoisomers of 1,2-substituted
cyclohexane
Cyclohexane is a cycloalkane with the molecular formula . Cyclohexane is non-polar. Cyclohexane is a colorless, flammable liquid with a distinctive detergent-like odor, reminiscent of cleaning products (in which it is sometimes used). Cyclohexan ...
s behave like meso compounds at room temperature in most cases. At room temperature, most 1,2-disubstituted cyclohexanes undergo rapid ring flipping (exceptions being rings with bulky substituents), and as a result, the two cis stereoisomers behave chemically identically with chiral reagents.Vollhardt, K. Peter C. Organic Chemistry: Structure and Function, Fourth Ed. 2003. W.H. Freeman and Co. New York. pp. 187. At low temperatures, however, this is not the case, as the
activation energy
In chemistry and physics, activation energy is the minimum amount of energy that must be provided for compounds to result in a chemical reaction. The activation energy (''E''a) of a reaction is measured in joules per mole (J/mol), kilojoules pe ...
for the ring-flip cannot be overcome, and they therefore behave like enantiomers. Also noteworthy is the fact that when a cyclohexane undergoes a ring flip, the absolute configurations of the stereocenters do not change.