|
These are rules that allow for the universal
description of the geometries (and configurations) about stereocentres.
The first thing to do, is to assign priorities:
To do this, we simply place the substituents on a stereocentre
in order of their atomic numbers (starting with the highest first). To
distinguish between different isotopes, rank the heaviest as higher
priority.
In cases where there are two substituents of the same mass, then
the masses of their nearest neighbours are compared, until they
can be distinguished. For example:
 |
Chlorine has the highest atomic number, and therefore
has highest priority. Second comes the acid group, because
although both it and the methyl group have carbon atoms attached
to the stereocentre, the carbon of the methyl only has hydrogen
atoms attached, whereas the carbon atom of the acid group has oxygen
atoms attached. As oxygen is heavier than hydrogen, the acid group
has second priority, followed by the methyl, and lastly, the hydrogen
atom. |
Now we have established the order of priority, we
can set about determining the absolute configuration. This
is done by imagining that we are rotating the molecule in question
so the lowest priority group (hydrogen in our case) points away
from us. Now imagine looking along the line formed between
the stereocentre and the hydrogen. It should look something
like this:
Now we simply follow the direction of decreasing priority.
That is, count from 1 to 3. In doing so, we notice that the
groups are anticlockwise, and this
is designated as an 'S' configuration.
Had we chosen the other enantiomer of the molecule above, the situation
would have been:
 |
Which, viewed as before, looks like: |
 |
This time, the groups decrease in priority in a clockwise
manner, and this is designated as an 'R' configuration.
|
|