1,1´,1´´-(2,4,6-Trihydroxybenzene-1,3,5-triyl)triethanone tautomerism revisited.

Poul Erik Hansen, Fadhil S. Kamounah, Diana Zhiryakova, Yana Manolova, Luidmil Antonov

Research output: Contribution to journalJournal articleResearchpeer-review


It has recently been suggested that 1,1′,1′′-(2,4,6-trihydroxybenzene-1,3,5-triyl)triethanone may be tautomeric. Using 13C NMR chemical shifts and deuterium isotope effects on 13C chemical shifts, it is demonstrated that this is not the case. This compound occurs as a strongly hydrogen bonded benzene structure with hydrogen bonds between OH groups and the acetyl groups in both non-polar and hydrogen donating solvents. Quantum-chemical calculations using MP2 and M06-2X methods show substantial preference for the phenol structure in both the gas phase, and in cyclohexane and methanol. In addition, conventional UV–vis spectroscopy data suggest not tautomeric, but aggregation behaviour of the molecule in methanol and acetonitrile.
Original languageEnglish
JournalTetrahedron Letters
Issue number2
Pages (from-to)354-357
Number of pages4
Publication statusPublished - Jan 2014


  • tautomerism
  • aromatic hydroxycompounds
  • isotope effects

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