Self-Complementarity of Oligo-2-aminopyridines: A New Class of Hydrogen-Bonded Ladders

A new class of hydrogen-bonded ladders based on hydrogen-bonded dimerization of oligo-α-aminopryidines has been demonstrated. Jorgensen's model can be successfully applied to this hydrogen-bonding system in nonpolar solvents. The results show the competitive enthalpy/entropy compensation
relationship upon dimerization. Although increasing the number of hydrogen-bonding interactions would
enhance the hydrogen-bonding stabilization enthalpy, this stabilization enthalpy per unit would be partially
sacrificed to compensate for the entropy loss due to dimerization. These results clearly support the
importance of preorganization in designing hydrogen-bonding guest−host molecules.