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Heats of formation of Hydrogen bond complexes between pyridine and alcohols or substituted phenols are measured in carbon tetrachloride solution by calorimetry. The obtained energies are compared with the acid ionization constants in water and the a values of the phenol substituents. Steric hindrance lowers the bond energy. However the heats of complex formation are linearly related to the frequency shift of the hydroxyl absorption brought about by the Hydrogen bond interaction.
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Neerinck et al. (1966) studied this question.
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