Association between Polar Molecules. III. 1H and 13C NMR Studies on the Dipole Association of Acetonitrile Derivatives with Tetramethylurea and Dibutyl Sulfoxide in Nonpolar Solvents

Abstract
Dipole association between acetonitrile derivatives and polar substances such as tetramethylurea and dibutyl sulfoxide is investigated in nonpolar solvents. Association parameters and thermodynamic parameters are derived and discussed in relation to the substituent constants. 1H and 13C NMR chemical shifts show that the major structures of the associate are antiparallel. Association energies are also determined using semiempirical MNDO MO method, which supports the experimental results for energies as well as structures.

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