Which of the following cannot be used as Lewis acid in the electrophilic substitution of benzene?
- $\ce{BF3}$
- $\ce{SbCl3}$
- $\ce{FeCl3}$
- $\ce{PF3}$
My Attempt:
- $\ce{BF3}$ and $\ce{FeCl3}$ are Lewis acids.
- $\ce{PF3}$ though it has a filled s and p orbitals it can accept electrons from donors and expand its coordinate number up to six due to vacant d orbitals. It acts as a mild Lewis acid.
- $\ce{SbCl3}$ has a completely filled s,p,d orbitals so it can no longer accept electrons, hence doesn't act as a Lewis acid.
My answer is option (2) but the answer provided is (4), where am I going wrong?
Answer
The best answer I can give is that there is enough space on $\ce{Sb}$ in $\ce{SbCl3}$ for an additional Lewis Base to interact with a nonbonding orbital on the $\ce{Sb}$ atom. While $\ce{P}$ can be hypervalent, the LUMO in this case would be $\ce{P-F}$ $\sigma^\ast$, which is really high in energy (meaning that it doesn't easily accept electron density from other species in solution).
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