It is shown that the reaction of phenylglycidyl ether with model hydroxyamines proceeds at various initial rates. The reaction rate is greater with amines containing electron-donor groups. In the model compounds, complex formation by hydrogen bonds between hydroxyl groups and nitrogen atoms is of considerable importance. The differences in the dependence of the initial rates on reagent ratio for the chemically related model compounds, disubstituted aniline and tetrasubstituted m-phenylene diamine, is explained by the possibility of the formation of various types of intermolecular complexes with hydrogen bonds.