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OPTICAL ACTIVITY
- Since enantiomers are "handed" or "chiral",
they can be distinguished by other agents which are chiral. Thus, we can easily
tell, in using our right hand to shake hands with another person, whether
that person is using his left or right hand. There is a better "fit"
of the two right hands than there is of right hand to left hand.
- Chemically this occurs, as noted above, when enantiomers
react with another chiral compound. Both the original enantiomer and its reactant
distinguish left from right , so then one of the original enantiomers will
find a better energetic fit with the chiral compound than will the other.
- One physical property which distinguishes 2 enantiomers
is "optical activity". This term refers to the property of chiral
compounds (exclusively) of rotating the plane of plane-polarized light to
the right (clockwise) or to the left (counterclockwise).
- The two enantiomers have exactly the same ability to
rotate this plane, quantitatively, but they rotate it in opposite senses.
Thus, if one enantiomer rotates the plane by 10.5 degrees clockwise (considered
a positive rotation), the other rotates it by -10.5 degrees (i.e., in the
counterclockwise direction).
- Since the exact amount of the rotation of the plane by a
given enantiomer depends upon how much of that enentiomer the light encounters
as it passes through the solution, the measured rotation is divided by the
concentration of the enantiomer and by the path length of the polarimeter
cell to give a true measure of the inherent ability of the enantiomer to rotate
the plane of polarized light. This number is called the specific rotation.
Note that in deriving the specific rotation, the concentration is taken in
grams per mL, and the path length in decimeters. The magnitude of the rotation
also depends upon the wave length of the plane polarized light, so the a single
wave length is usually used, i.e., the sodium D line (529 nm),the line responsible
for the yellow color of sodium-vapor lamps.
- A positive (clockwise) rotation is sometimes called dextrorotation
and a ngetaive rotation is sometimes called levorotation
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