# Electronic effects of substituents in the benzyne mechanism

On the topic of nucleophilic aromatic substitution (S$$_N$$Ar) reactions, the benzyne mechanism is discussed. When considering the position of substitution, electronic and steric factors are mentioned. When considering electronic factors, effects of substituents on the ring are viewed rather differently, compared to how they are viewed in the conventional electrophilic aromatic substitution reaction.

Pg. 525 from Organic Chemistry (2nd ed.) shows the following diagram:

In the discussion of the benzyne mechanism, conventionally electron-donating groups are said to not be able to exert their donating effects and are even viewed as electron-withdrawing via the inductive effect. However, I cannot see why they behave in this way. Why is their donating effect no longer significant? Certainly, their p orbitals are still in conjugation with the rest of the $$\pi$$ system right?

However, if their electron-donating effects were more important, then we would observe ortho and para attack by the nucleophile, so as to generate the negative charge at the meta position, which is apparently not the case as experimentally observed.

Reference

Clayden, J., Greeves, N., & Warren, S. (2012). Organic Chemistry (2nd ed.). New York : Oxford University Press Inc