Inductive effect of phenyl ring

Question

I completely understand how phenyl group 'releases' or 'donates' electron through resonance, but how is that a phenyl group shows a weak -I effect, despite having electrons literally smeared on itself?

Answer 1

As the $\mathrm{s}$ characteristic of an atom increases, so too does its electronegativity. Proof of this can be seen when comparing the $\mathrm{p}K_\mathrm{a}$'s of 2-carbon hydrocarbons. The $\mathrm{p}K_\mathrm{a}$'s of $\ce{CH3 -CH3}$, $\ce{CH2 =CH2}$, and $\ce{CH ≡CH}$ are $51$, $44$, and $25$ respectively.

When considering phenyl group for what it is, a ring of six $\mathrm{sp^2}$-hybridized carbons, it is easy to see why it shows a strong electron withdrawing effect, and a weak electron donating effect. The electronegativity of the carbons make benzene a nucleophilic structure that does not easily give up its electron cloud.

Answer 2

in phenyl group the carbons are sp^2 hybridised which are having less s character and are thus electronegative in nature hence shows -I effect