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

Acta Crystallogr C. 2012 Apr;68(Pt 4):o179-82. doi: 10.1107/S0108270112013169. Epub 2012 Mar 31.

Abstract

The structure of the title compound, C(18)H(22)O(2), 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 (-102). 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 structure versus substituents in vicinal dialkynols could be fruitful.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Alkynes / chemistry*
  • Butanols / chemistry*
  • Hydrogen Bonding
  • Models, Molecular
  • Molecular Structure

Substances

  • 4,4'-(4,5-dimethyl-1,2-phenylene)bis(2-methylbut-3-yn-2-ol)
  • Alkynes
  • Butanols