The pitfalls of using JHF spin-spin coupling constants to infer hydrogen bond formation in organofluorine compounds

Theoretical decomposition of through space spin-spin coupling constants (SSCCs) in organofluorine compounds signal that intramolecular hydrogen bonds (H-bonds) are not the primary mechanism of transmission for SSCCs. Increasing solvent polarity may disrupt H-bonds, but not necessarily the JFH SSCC. Substituent effects may drastically alter the SSCC transmission pathway. Accurate SSCC analysis requires benchmarking theoretical calculations to support experimental data interpretation.

Automated summary

Theoretical decomposition of through space spin-spin coupling constants in organofluorine compounds suggests that intramolecular hydrogen bonds are not the primary mechanism for SSCC transmission. Increasing solvent polarity may disrupt hydrogen bonds, but not necessarily the JFH SSCC. Additionally, substituent effects can greatly alter the SSCC transmission pathway. Accurate SSCC analysis requires benchmarking theoretical calculations with experimental data interpretation.