# How is o-Fluorophenol more acidic than phenol even after having Hydrogen bonding?

Source: Concepts of Organic Chemistry by Dr OP Tandon, Himanshu Pandey, Dr AK Virmani Page no: 241

In the series of nitrophenols (Acidity order of nitrophenols), the para (p$$K_a$$ = 7.16) is slightly more acidic than the ortho (p$$K_a$$ = 7.2), so it could be said that the ortho substituted compound, which would be expected to be more acidic (if you assume that the resonance effects at ortho and para positions would be similar), but isn't, we have to look for some other explanation, and hydrogen bonding could stabilize the neutral molecule.
Well, even if the actual effect is stronger than 0.04 p$$K_a$$ units, the hydrogen bonding effect seems to be rather small, and is overcome in the fluorophenols by the $$-I$$ effect of fluorine. Just scratch out the words "H-bond decreases acidity". (Lightly.)