Understanding the effects of vicinal carbon substituents and configuration on organofluorine hydrogen-bonding interaction.

ABSTRACT: An investigation of C-F⋯H-O hydrogen bonds in the complexes CH _n XCH _n F⋯H₂O (n = 0, 1, 2; X = H, F, Cl, Br) was performed at the MP2/aug-cc-pVTZ level. We found that the electron-withdrawing halogen substituents on the vicinal carbon cause the fluorine atom, participating in the hydrogen bond formation, to be less negatively charged. Thus, the halogen groups weaken the strength of organofluorine hydrogen bond by inductive effect. The position of the substituents on the vicinal carbon affects the strength of the C-F⋯H-O interaction. Compared with that in other isomers, the electron withdrawing substituent in 1-fluoro-ethane with stagger conformation as well as in 1-fluoro-ethene with trans configuration much weakens the in

SUBMITTER: Jia Q 

PROVIDER: S-EPMC9090643 | biostudies-literature | 2018 Nov

REPOSITORIES: biostudies-literature