Past exam of the chemistry course of the year 3 of the natural sciences course of the University of Cambridge / 2021 / Paper 1 / 2 / b

There are two carbon-placement isomers, represented by the cyclic base sequences $\mathrm{CCBBB}$ and $\mathrm{CBCBB}$. The carbon vertices are adjacent in the first and separated by one boron vertex in the second. Rotation or reversal of a sequence does not produce another constitutional isomer.

Each arrangement has a reflection symmetry that exchanges a pair of boron sites while leaving the third distinct. Consequently each can give two ${}^{11}\mathrm{B}$ environments, with site populations $2:1$, in a proton-decoupled NMR spectrum. This assumes that the hydrogen and carbonyl arrangements preserve, or rapidly average to, the corresponding skeletal symmetry. Two peaks alone neither choose between the two skeletons nor establish a unique hydrogen arrangement; accidental overlap or fluxionality can also reduce the number of observed signals.