# Phenol's resonance structure doesn't match NMR

I've asked a question before and quickly realised that the resonance/mesometric effects played a large role in determining the C-13 NMR spectrum of phenol, shown below.

This is the resonance structure of phenol:

But given this, I would have expected the carbons at $$b$$ to be more shifted than the ones at $$d$$. This is because although they both have partial negative charges, the inductive effect of the hydroxy group on $$a$$ should make $$b$$ more deshielded than $$d$$.

Why is this?

• now it seems that you're accounting only for the mesomeric effect and not the induction. Consider the combined effects, especially with regard to how the positive charge distributes. Jun 11 at 14:54
• @Andrew If I account for the inductive effect, shouldn't that would mean that d should be more shielded than b? This is because b is closer to the positive oxygen which will be withdrawing electron density. So why isn't this the case? Jun 12 at 0:11
• I think the answer is gonna be more complicated than just inductive/resonance effects --- 13C shifts are not very straightforward, it's tempting to think of them like we do 1H shifts, but the underlying reasons for the chemical shifts are rather different Jun 12 at 0:26