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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 gas-phase acidities of meta-and para-substituted phenols have been calculated at the B3LYP/6-311+G, MP2/6-311+G, MP2/6-311++G, and MP2/6-311+G(2df,2pd) theoretical levels. The larger basis sets give the more satisfactory DeltaHacid values that are correlated with the observed acidities with a slope close to unity.