A solvent-free organic synthesis from solid-state reactants through autogenous fusion due to formation of molecular complexes and increasing alcohol nucleophilicity

摘要

Crystalline imidazole (IM,mp 361-364 K)fuses autogenously immediately after making contact at room temperature with menthol (MT,mp 316 K)as a consequence of the hydrogen bond.Autogenous fusion is triggered by the recombination of the hydrogen bonds from the homogeneous ones (MT-MT)stabilizing MT crystals to the heterogeneous ones between OH of MT and N of IM to form an intermediate molecular complex at a eutectic composition.Formation of molecular complex parallels the increase in the nucleophilic affinity of MT by the intermolecular hydrogen bonds,as confirmed by the peak shift of ~1H NMR as well as by DFT computation.