Formation of a Limited Solid Solution in a Crystalline Azide of the 1,5-Dihydro-2H-Pyrrol-2-One Series as a Local Loss of Chiral Discrimination

Abstract

A new nitrogen-containing heterocycle, 4-azido-3-bromine-5-hydroxy-1-(2-hydroxyethyl)-1,5-dihydro-2H-pyrrol-2-one, is prepared by the interaction of a 5-methoxy-2(5H)-furanone 4-azido derivative with 2-aminoethanol. It is established by XRD that this compound crystallizes as a limited solid solution containing equal amounts of hetero- and homochiral H-bonded dimers. It is shown by quantum chemical methods that both dimers are stable and exhibit similar energies of intradimer interactions. The reasons of local chiral discrimination loss are discussed.