4,4′-(4,5-Dimethyl-1,2-phenylene)bis(2-methylbut-3-yn-2-ol): structural variation in vicinal dialkynols

Abstract

The structure of the title compound, C18H22O2, contains two non-equivalent molecules which differ primarily in the location of the –OH groups on opposite sides or on the same side of the molecular plane. Inversion-symmetric pairs of molecules form intermolecular O—H...O hydrogen-bonded tetrameric synthons that link non-equivalent molecules into an approximately square double layer parallel to (\overline{1}02). Recently reported fluorinated analogues [Kane, Meyers, Yu, Gerken & Etzkorn (2011).Eur. J. Org. Chem.pp. 2969–2980] have significantly different structures of varying complexity that incorporate intramolecular hydrogen bonding and suggest that further study of structureversussubstituents in vicinal dialkynols could be fruitful.