Electronic Trend Matrix:
Electron Withdrawing Groups (-I): Stabilize enolate charge $$\longrightarrow$$ Increase acidity (e.g., $$-\text{NO}_2$$, $$-\text{F}$$, $$-\text{Cl}$$)
Electron Donating Groups (+I): Destabilize enolate charge $$\longrightarrow $$Decrease acidity (e.g., $$-\text{CH}_3$$
Concept: Acidic strength depends directly on the stability of the conjugate base carboxylate anion. The spatial distribution follow the strict DNB Rule (Distance, Number, Strength). Proximity of a negative inductive group dominates over the total count, which in turn dominates over the raw baseline electronegativity strength of the atom.