Strength from weakness: opportunistic CH⋯O hydrogen bonds differentially dictate the conformational fate in solid and solution states

Abstract

We show that the CH⋯O hydrogen bond can be opportunistic to differentially dictate the conformation of cyclitols in solution and solid states. While several intermolecular CH⋯O stabilize the chair-conformation in the solid, single intramolecular CH⋯O stabilizes an otherwise unfavorable boat-conformation in solutions analogous to the boat-conformation of cis-1,4-cyclohexanediols by OH⋯O bonds.