1 The Department of Science, Systems and Models, Roskilde University2 Funktionelle Biomaterialer, Department of Science and Environment, Roskilde University3 Department of Science and Environment, Roskilde University4 Bulgarian Academy of Sciences
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.
Tetrahedron Letters, 2014, Vol 55, Issue 2, p. 354-357