Reaction of N-allenyl-1H-pyrrole-2-yl-carbaldehyde with hydroxylamine: a quantum-chemical model

Abstract The mechanism of the reaction between hydroxylamine and N-allenylpyrrole-2-carbaldehyde has been studied using quantum-chemical methods (B2PLYP-D2/6-311+G**//B3LYP/6-31+G*). It is shown that the calculations should take into account the solvent molecules. Solvent molecules provide both proton transfer and adequate reproduction of activation barriers. It is found that two solvent molecules are necessary for modeling oximation reaction, whereas only one solvent molecule is sufficient for the cyclization step.