Pushing the limits of the hydrogen bond enhanced halogen bond—the case of the C–H hydrogen bond
Daniel A. Decato, Jiyu Sun, Madeleine R. Boller, Orion B. Berryman
Abstract
enhancement over a control lacking the C-H⋯I-C interaction. X-ray crystallographic analysis demonstrated C-H hydrogen bonds and bidentate conformations with triflate and iodide anions, yet the steric bulk of the central functional group seems to impact the expected trends in halogen bond distance. In solution, anion titration data indicated elevated performance from the receptors that utilize C-H Hydrogen Bond enhanced Halogen Bonds (HBeXBs). Collectively, the results suggest that even modest hydrogen bonds between C-H donors and iodine acceptors can influence molecular structure and improve receptor performance.
Topics & Concepts
Hydrogen bondHalogen bondChemistryIntramolecular forceHalogenSteric effectsDenticityCrystallographyMoleculeLow-barrier hydrogen bondPhotochemistryStereochemistryAlkylCrystal structureOrganic chemistryCrystallography and molecular interactionsCrystal structures of chemical compoundsMolecular Sensors and Ion Detection