Chemoselectivity of aminomethylation of amino- and alkoxy- ethanols in charge units of general theory of acids and bases Chemistry

Abstract

The evidence on the violation of chemoselectivity of aminomethylation of dimethyl- and diethylaminoethanol, which occurs under the influence of hydrogen bond was received. The same hydrogen bond occurs in the oxygen analogues of aminoethanols and β-alkoxietanols, but contrary to expectations, it is not accompanied by a change in the chemoselectivity of the reaction. We propose a rationale to explain the differences in the properties of these molecules, using charge units of the ionic character of the bond.