Consider the following set of stereoisomers of tartaric acid (Please
note the axial bonds are deliberately, and unnaturally, elongated
to make the diagrams clearer) :

|
In each case, there are two stereocentres.
1 and 2 are clearly enantiomers, however, what may not be
immediately apparent is that 3 and 4 are in fact the same
molecule. Molecules that have stereocentres, yet are
themselves achiral (like 3/4) are known as meso
compounds. |
Conformation describes the relative
location of atoms in a molecule. This is best illustrated
by example: The following molecule is shown in two different conformations
(the one on the left is of low energy, and the one on the right
is of high energy), they are known as staggered
(left), and eclipsed (right).
A conformational change can be (and is) achieved without breaking
any bonds.
Of course, the two conformations shown above are merely
convenient to represent; there are an infinite number of possible
conformations of the molecule above, and indeed of any molecule
with a small rotational energy barrier round a single bond.
Configuration describes
the exact three dimensional location of each atom in space, and
their connectivities.
To change a configuration, bonds must be broken.
There are special rules to describe the absolute configuration
of a molecule. These are known as Cahn-Ingold-Prelog
rules, and will be dealt with on the next page. Note that
in the meso form of tartaric acid, the configurations of the two
stereocentres are opposite. The molecule is descibed as being internally
compensated, and thus has no optical activity.
Epimerisation is the process, during
which, a molecule with more than one stereocentre undergoes a change
in configuration at one of its stereocentres. 1 and 2 above are
both epimers of 3/4.
|