Structure is at https://chemapps.stolaf.edu/jmol/temp/cip-c13-test.png
John wrote back to say
1) "The SMILES should be [13C@@H]12C3C1.C2=CC3"
-- Thanks for that. Duh!
2) "The designation is S"
I'm pretty sure it's 1R 5R.
For the chirality at C1, the only question is whether C5 beats C2. The
highest-priority path via C1-C5 is C1-C5-C6 rather than C1-C5-C2 because
the duplicated atom C1 with mass 13 coming around the cyclopropane ring
C1-C5-C6-(C1) beats the alternative pathway C1-C5-C4-C3 based on Rule 2
(higher mass). And then that pathway beats C1-C2-C3-C4 for the same reason.
So C5 has higher priority than C2.
It is opposite when there is no isotope. In that case, C1-C2-C3-C4 beats
C1-C5-C6-(C1) due to the lack of substituents on the duplicated atom C1
compared to C4 in the *next round*, giving 1S 1R for the original model
that Mikko sent me.
Am I wrong?
Bob
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