D. Sevenard, O. Kazakova, Ralf‐Matthias Schoth
Oct 11, 2011
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Journal
Journal of Chemical Crystallography
Abstract
The crystal structures of 2,5-bis(trifluoroacetyl)cyclohexane-1,4-dione (1) and o,o′-bis(trifluoroacetyl)-p-cresol (2) is reported. The first compound crystallizes in monoclinic space group P21/n with a = 6.5040(10), b = 10.1610(10), c = 8.2420(10) Å, β = 91.690(10)° and V = 0.54445(12) nm3. Double enolization (U-structure) with a considerable electron density delocalization in the enolone backbone was established in this case. Phenol 2 crystallizes in triclinic space group P-1 with a = 7.0690(10), b = 9.4890(10), c = 9.8190(10) Å, α = 103.720(10), β = 110.760(10), γ = 102.150(10)° and V = 0.56598(12) nm3. In contrast to CDCl3 solution, a “bifurcate” structure of 2 with jumping OH proton is quenched: only one of both trifluoroacetyl moieties is bonded by intramolecular hydrogen bond.Graphical AbstractThe structural peculiarities of 2,5-bis(trifluoroacetyl)cyclohexane-1,4-dione (1) and o,o′-bis(trifluoroacetyl)-p-cresol (2) in solid state and solution (especially with respect to hydrogen bonding features) are discussed.