Intramolecular Hydrogen Bonding in 2-(Substituted Amino-) Methyl-4-Acetamidophenol

Intramolecular H-bonding in the titled compounds have been detected by IR and UV. The effect of such bonding on the phenolic dissociation constant (pK_a), determined by spectrophotometric titration, provides additional support to the observed data. The hydrogen bond energy, calculated from shift in λmax, roughly parallels the basicity of the parent amine on the side chain.