Enantiomers, Diastereomers & Meso Compounds Stereoisomers which are related to each other as mirror images are called

enantiomers. Enantiomers can contain any number of stereogenic centers, as long as each center is the exact mirror image of the corresponding center in the other molecule.

If one or more of these centers differs in configuration, the two molecules are no longer mirror images, but are totally different chemical compounds with differing physical and biological properties. Stereoisomers which are not enantiomers are called diastereomers.

For a molecule with multiple chiral centers, the number of possible diastereomers is given by the equation: x = 2n Where x is the number of possible isomers and n is the number of stereogenic centers. Thus, for molecules with two stereogenic centers there are four possible stereoisomers. For cholesterol, with eight stereogenic centers, there are 256 possible stereoisomers, etc. A third type of stereoisomer which must be considered is a meso compound. A meso compound contains at least two stereogenic centers, yet the molecule itself is not chiral. This is because meso compounds contain an internal plane of symmetry; the molecule can be split by an imaginary mirror so that all atoms on one side of the mirror are the exact reflection of the atoms on the other side. This can be seen below for cis-1,2dimethylcyclopentane; there are two chiral centers in the molecule since the two carbons labeled with the red asterisk are each bonded to four different groups. A mirror placed through the molecule, along the plane indicated by the dashed line, will exactly bisect the molecule with all groups exactly reflected by their counterparts on the other side of the "mirror".

Assigning Absolute Configuration: The Cahn-Ingold-Prelog R/S System The rules for assignment of priorities in order to assign absolute configuration are based on the same set of rules which have been used previously for assigning E and Z stereochemistry. The procedure is fairly straightforward for simple compounds; first, you assign priorities to the groups attached around the chiral center. Next, you rotate the molecule so that the lowest priority group is pointing towards the back (away from you). Finally, you examine the remaining group priorities and determine if they are now arranged so that the priority decreases clockwise (R, for rectus) or counterclockwise (S, for sinister). These rules are restated below, with examples: 1. Examine the four atoms directly attached to the chiral center in question. Assign priorities in order of decreasing atomic number; the atom with the highest atomic number is #1, the next is #2, etc.

2. If a decision regarding priority cannot be reached using Rule #1, compare the atomic numbers of the second atoms in each substituent, then the third, etc., until a difference is found.

3. Multiple bonds count twice (or three times) when examining substituents.

4. Once the priorities have been assigned, rotate the molecule in space so that the lowest priority group is pointing back. Connect the three remaining groups in order of decreasing priority and examine the direction of the resulting rotation. Rotation which is clockwise is termed R (rectus; right) and rotation which is counterclockwise is termed S (sinister; left).