Insight Into the Conformational Arrangement of a Bis-THF Diol Compound Through 2D-NMR Studies and X-Ray Structural Analysis

Abstract

The conformational arrangement of an all-threo bis-THF diol compound, synthesized through the RuO4-catalysed oxidative bis-cyclization of farnesyl acetate, was determined via crystallographic analysis and detailed 2D-NMR solution studies. The bis-THF compound crystallizes in the orthorhombic Pbca space group, with unit cell parameters a = 10.496(1), b = 17.974(1), c = 19.777(2) A, Z = 8. The final refinement converged to R 1 = 0.0484 for 4714 independent observed reflections having I > 2σ(I). There is a good agreement between the solution molecular conformation determined by 2D-NMR and the X-ray molecular conformation. The molecule adopts a folded, horse shoe-type conformation both in solution and in the crystal, that suggests aptitude to coordinate cations. Additionally, in the crystals, the molecular conformation is stabilized by intramolecular and intermolecular H-bonding. 2D-NMR and X-ray studies indicate that the bis-THF shown adopts a folded, horse shoe-type, conformation both in solution and in the crystal, that suggests aptitude to coordinate cations.