Abstract
When a saturated aqueous solution of phthalic acid is treated with excess fluoride ion the acid dissolves completely. This fluoride ion assisted dissolution is not shown by isophthalic or terephthalic acids. Two fluoride ions are required for each phthalic acid molecule taken into solution. Concentration of such solutions affords phthalic acid, sodium hydrogen phthalate, and sodium hydrogen difluoride; therefore the dissolution reaction is C 6H 4(CO 2H) 2 + 2F − = {C 6H 4(CO 2) 2H} − + HF 2 −. The driving force for this unexpected dissolution process is the formation of strong covalent hydrogen bonds in the hydrogen phthalate and hydrogen difluoride anions. The dissolution of phthalic acid in the presence of fluoride ion does not proceed by the same mechanism as the fluoride ion assisted dissolution of succinic acid reported by Emsley and Jones.
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