Two- and three-component mixtures were prepared using the monosubstituted urea of 1-methylurea (Um) and 1-hydroxyurea (Uh) as hydrogen bond donors, and guanidine monohydrochloride (GuHCl) as a hydrogen bond acceptor. Differential scanning calorimetry (DSC) thermograms and the solution-state nuclear magnetic resonance (NMR) spectra of the mixtures were compared with those of a deep eutectic solvent (DES) composed of urea (U) and GuHCl. At room temperature, 2Um-GuHCl was a DES in the supercooled state unlike solid state 2 U-GuHCl. Conversely, 2Uh-GuHCl did not form a DES. The methylation of urea resulted in the weakening of the hydrogen bonding of Cl− with others.
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Umecky et al. (2024) studied this question.
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