Imidazole structures have occupied a unique position in heterocyclic chemistry as a synthetic precursor to imidazole salts ultimately for the formation of N-heterocyclic carbenes (NHCs). NHCs have proven to be excellent ligands in metal-based catalysis. The synthesis and the crystal structure of 1H-imidazole-1-methanol, C4H6N2O, are described. This compound comprises an imidazole ring with a methanol group attached at the 1-position affording an imine nitrogen atom able to receive a hydrogen bond and an alcohol group able to donate to a hydrogen bond. This imidazole methanol crystallizes with monoclinic (P21/n) symmetry with three symmetry-unique molecules. These three molecules are connected via O—H to N hydrogen bonding in a head-to-tail configuration to form independent three-membered macrocycles. Crystalline 1H-imidazole-1-methanol is directly obtained from the reaction of imidazole and paraformaldehyde using Schlenk techniques and spectroscopy. Complete results of this work will be presented.

Synthesis and crystal structure of 1H-imidazole-1-methanol

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