New insights into the structure of glycols and derivatives: A comparative x-ray diffraction, raman and molecular dynamics study of ethane-1,2-diol, 2-methoxyethan-1-ol and 1,2-dimethoxy ethane

Abstract

In this study, we report a detailed experimental and theoretical investigation of three glycol derivatives, namely ethane-1,2-diol, 2-methoxyethan-1-ol and 1,2-dimethoxy ethane. For the first time, the X-ray spectra of the latter two liquids was measured at room temperature, and they were compared with the newly measured spectrum of ethane-1,2-diol. The experimental diffraction patterns were interpreted very satisfactorily with molecular dynamics calculations, and suggest that in liquid ethane-1,2-diol most molecules are found in gauche conformation, with intramolecular hydrogen bonds between the two hydroxyl groups. Intramolecular H-bonds are established in the mono-alkylated diol, but the interaction is weaker. The EDXD study also evidences strong intermolecular hydrogen-bond interactions, with short O···O correlations in both systems, while longer methyl-methyl interactions are found in 1,2-dimethoxy ethane. X-ray studies are complemented by micro Raman investigations at room temperature and at 80◦C, that confirm the conformational analysis predicted by X-ray experiments and simulations.