Abstract

1. The basicity of o-aminomethylphenols in nitromethane, acetonitrile, and ethanol is lower in comparison with benzylamines, which do not have any intramolecular hydrogen bonds. 2. The influence of the intramolecular hydrogen bond on the basicity of the o-aminomethylphenols increases in the following series of solvents: ethanol<water<acetonitrile-nitromethane. 3. Between the values of pKa of the o-aminomethylphenols and benzylamines in water, ethanol, nitromethane, or acetonitrile, linear correlations are obtained with slopes close to unity. 4. The relationship between pKa in nitromethane and in acetonitrile is common for primary, secondary, and tertiary alkylamines, benzylamines, o-aminomethylphenols, anilines, and pyridine.

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