Abstract
A series of 3-alkyltetrahydropyranyl 4-sulfates, containing 9-15 carbon atoms in the alkyl group, has been synthesized, purified, and characterized. These materials have unusually high solubility in water. Surface tension measurements on aqueous solutions of these compounds have been used to calculate surface excess concentration, area/molecule at the liquid-air interface, critical micelle concentration, and efficiency and effectiveness of surface tension reduction. Values are compared with those for sodium n-alkyl sulfates. These data indicate that the tetrahydropyran group in these compounds is lying in the interface with the alkyl group oriented away from the aqueous phase. Using a new method for calculating standard free energies of adsorption and micellization, we calculated the standard free energy of adsorption of the tetrahydropyran group at the aqueous solution-air interface at 25/sup 0/C to be -1.7 kJ mol/sup -1/, somewhat less than that for a methylene group (-3.0/sub 3/ kJ mol/sup -1/) in the alkyl chain of the molecule, while the standard free energy of micellization of the tetrahydropyran group is shown to be -3.0 kJ mol/sup -1/, somewhat more than that for a methylene group (-2.5/sup 8/ kJ mol/sup -1/) in the alkyl chain. 4 tables, 2 figures.
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