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• W2100088631 abstract "Abstract The X-ray crystal structure of 2-(2′,4′-dioxo-3′-pentyl)-5,5-dimethyl-2-oxo-1,3,2-dioxaphosphorinane ( II ) reveals significant half-chair distortion of the axially oriented cis-enol ring and the tilt of the methyl groups in the enol ring away from the phosphorinane internal oxygen atoms due to their repulsive interactions. The molecule also undergoes in-plane deformations. R (O⋯O)=2.410 A in the enol moiety indicates very strong hydrogen bonding. The enol form, δ OH and stereochemical assignments were obtained from 1 H and 31 P NMR and IR measurements in comparison with the planar 4,6-dimethyl isomer ( I ) containing an equatorially oriented enol ring. The value of Δ H ° for the axial—equatorial conformational equilibrium in CH 2 Cl 2 was found to be −0.440 ± 0.100 kcal mol −1 in favour of the non-planar enol. Thermodynamic parameters for the keto—enol equilibrium in the isomeric compounds ( I ) and ( II ) were obtained in CH 3 CN providing evidence for a smaller enthalpy of enolization of the non-planar enol." @default.
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• W2100088631 date "1994-08-01" @default.
• W2100088631 modified "2023-10-18" @default.
• W2100088631 title "The non-planarity of the enol tautomer of phosphorus-substituted pentane-2,4-dione. Influence on hydrogen bonding strength, enol content and enthalpic stabilization" @default.
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• W2100088631 doi "https://doi.org/10.1016/0022-2860(94)08303-7" @default.
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