53343-91-2Relevant articles and documents
NMR and X-ray crystallographic studies of the conformation of a 3,4,6-triphenyl-δ-lactone
Fuller-Stanley, Jean A.,Loehlin, James H.,Bolin, Kimberly A.,Fairbrother, Genevieve,Nazaire, Fausta
, p. 27 - 31 (2007/10/03)
1-Oxa-3S,4S,6R-triphenyl-2-cyclohexanone and its enantiomer were synthesized, and the structure was determined by NMR and X-ray crystallography. The X-ray crystal structure showed that the δ-lactone adopts a boat conformation in the solid. The X-ray data showed a shortened C-O bond between the carbonyl carbon and the ether oxygen, consistent with delocalization involving the ester group. 1H and 13C NMR measurements in acetone-d6 showed that the lactone is biased in favor of a boat conformation. In the less polar solvent chloroform-d1, changes in the 1H NMR coupling constants indicate a shift in the equilibrium in favor of a less rigid twist-boat conformation. The IR absorption of the lactone carbonyl at 1740 cm-1 would suggest a half-chair conformation inconsistent with the dominance of the boat forms shown by NMR and X-ray.
