When salicylic acid deprotonates (losing the proton from the carboxyl group) it forms a hydrogen bond with between the oxygen in the carboxylate anion and the hydrogen in the alcohol group. However, surely there will be a steric clash between these groups which would surely be make more significant by the long hydrogen bond? Could the hydrogen bond still form with the carboxyl group twited out of the plane? Also, why doesn't it hydrogen bond intramolecularly before deprotonation which would disfavor the loss of a proton?
