ENTHALPIES OF INTRAMOLECULAR HALOGEN–HYDROXYL INTERACTIONS

Abstract
Enthalpies of halogen–hydroxyl interactions have been evaluated for the 2-halophenols in carbon tetrachloride. These values, in −kcal/mole, corrected for the temperature dependence of absorptivity coefficients, are Cl = 1.44, Br = 1.21, and I = 1.08. From enthalpy differences measured in unsymmetrical 2,6-dihalophenols, it is shown that the interaction in 2-fluorophenol lies between those in 2-bromophenol and 2-iodophenol, thus reaffirming the order Cl > Br > F > I.