Equilibrium constants for self-association through hydrogen bonding have been determined by nuclear magnetic spectroscopy for three N-monosubstituted amides in dioxane solution at five temperatures in the range 20 to 60'. The free energy and enthalpy changes for association decrease in the order: N-methylacetamide > N-isopropylacetamide > N-tert-butylacetamide. The measured equilibrium constants and enthalpies are milch smaller in dioxane than in carbon tetrachloride. The low values for the enthalpies are interpreted as measuring the difference in energy between forming an amide-amide hydrogen bond and breaking an amidedioxane hydrogen bond.(1) This work was supported by a grant from the Academic Dean's Fund of Northern Illinois University.(2) This work is taken in part from the dissertation of C. Y . C.submitted in partial fulfillment of the requirements for the M.S. degree, Northern Illinois University, 1970.(3) S.
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