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Effects of substituents on the acidity of phenols: Existence of electron attracting group, (for example-NO2, -X, - NR, -CN, -CHO, -COOH) on the benzene ring increases the acidity of phenol since it enables the ring to draw much more electrons from the phenoxy oxygen and so releasing easily the proton.
The effect of the substituent on the conjugate acid or base influences the Ka (equilibrium constant) of the ionization, which in turn influences the pKa or acid strength. For basic compounds, the acid strength of the conjugate acid can then be related to the pKb, or base strength. (Note: Always draw the ionization scheme to express Ka with the acid on the left and the base on the right).