What does R configuration mean?
1 Answer
It is a stereochemical label to indicate the relative spatial orientation of each atom in a molecule with a non-superimposable mirror image.
R indicates that a clockwise circular arrow that goes from higher priority to lower priority crosses over the lowest priority substituent and that lowest-priority substituent is in the back.
The R and S stereoisomers are non-superimposable mirror images, which means if you reflect them on a mirror plane, they do not become the exact same molecule when you overlay them.
When you label a molecule as R or S, you consider the priorities of each substituent on the chiral carbon (connected to four different functional groups).
Let's take this chiral amino acid for example:
)
Some general ways you could determine the priorities are:
- HIgher atomic number of the directly-attached atom gives higher priority
- Atomic number of the atom attached to the one is considered in step 1 if two substituents have the same first atom
- Higher number of same-atom branches determines greater priority if the overall substituents are too similar (e.g. isopropyl has higher priority than ethyl)
With (R)-alanine:
"NH"_2NH2 has priority 1 due to highest atomic number for"N"N ."COOH"COOH has priority 2 due to the higher atomic number of"O"O vs."H"H in"CH"_3CH3 "CH"_3CH3 has priority 3 as a result."H"H has priority 4.
Now, if you draw a circular arrow starting at
)
Since the lowest priority atom is in the back, the clockwise arrow corresponds to the R configuration.
If you had started from the same R configuration but oriented
If you reflect the same R configuration over a mirror plane, keeping the orientations of
If you start from S configuration B, and flipped it over a vertical axis (literally rotating
