Competing HB acceptors: an extensive NMR investigations corroborated by single crystal XRD and DFT calculations

Abstract

A series of N-benzoylanthranilamide derivatives have been synthesized with the substitution of competitive HB acceptors and investigated by NMR spectroscopy and single crystal XRD.

Molecular dynamics and NMR reveal the coexistence of H-bond-assisted and through-space JFH coupling in fluorinated amino alcohols

“…Heteronuclear nOe (nuclear Overhauser effect) was observed between H8 and fluorine atom, indicating spatial proximity between these nuclei and bringing to the discussion the possibility of a through-space transmission pathway via intramolecular H-bond ( 1h J FH8 ), instead of a solely through bond transmission pathway ( 4 J FH8 ). Recently, studies conducted by Takahashi and coworkers 48,49 and by Suryaprakash and coworkers 50–53 have also employed 1 H– 19 F HOESY experiment to confirm the presence of intramolecular H-bond. What is intriguing about these compounds is the presence of this kind of interaction in a polar solvent such as DMSO- d 6 , once it is expected that the solvent molecules would prefer to interact with the solute, thus breaking the intramolecular H-bond.…”