Crystal structure of 1H-imidazole-1-methanol.

Megan M Wysocki,Deidra L Gerlach,Gorana Puzovic,Keith L Dowell,Eric W Reinheimer

doi:10.1107/s2056989022002614

Megan M Wysocki, Deidra L Gerlach + Show 3 more

Open Access

https://doi.org/10.1107/s2056989022002614

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Abstract

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 nitro-gen 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 mol-ecules. These three mol-ecules are connected via O-H⋯N hydrogen bonding in a head-to-tail configuration to form independent three-membered macrocycles.

Highlights

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
Imidazole structures have occupied a unique position in heterocyclic chemistry as a synthetic precursor to imidazole salts for the formation of N-heterocyclic carbenes (NHCs) (Jahnke & Hahn, 2016)
NHCs have proven to be excellent ligands in metal-based catalysis (Enders et al, 2007). 1H-Imidazole-1-methanol, the molecule highlighted in this article, is a precursor to form the NHC moiety of a larger tridentate ligand being developed

Summary

Chemical context

Imidazole structures have occupied a unique position in heterocyclic chemistry as a synthetic precursor to imidazole salts for the formation of N-heterocyclic carbenes (NHCs) (Jahnke & Hahn, 2016). Nitrogen heterocyclic carbenes (NHC) were first established by Skell in the 1950s and have been developed by Fischer and his students who introduced carbenes into organic and inorganic chemistry in 1964 (Herrmann & Kocher, 1997). 1H-Imidazole-1-methanol, the molecule highlighted in this article, is a precursor to form the NHC moiety of a larger tridentate ligand being developed. This molecule’s synthesis and characterization has previously been reported by DeBerardinis et al (2010), the crystal structure and structural properties have not. Crystalline 1H-imidazole-1-methanol is directly obtained from the reaction of imidazole and paraformaldehyde

Structural commentary

Supramolecular features

Database survey

Synthesis and crystallization

Refinement

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