The pitfalls of using 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 th...

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Bibliographic Details
Published inChemical communications (Cambridge, England) Vol. 59; no. 99; pp. 14661 - 14664
Main Authors Cariello, Guilherme, Zeoly, Lucas A, Piscelli, Bruno A, Lectka, Thomas, Cormanich, Rodrigo A
Format Journal Article
Published 12.12.2023
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Summary: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 J FH SSCC. Substituent effects may drastically alter the SSCC transmission pathway. Accurate SSCC analysis requires benchmarking theoretical calculations to support experimental data interpretation. Shedding light on 'through space' spin-spin coupling constants (SSCCs), this study challenges hydrogen bonding's dominance in JFH SSCC transmission on organofluorine compounds. Steric, substituent and solvent effects considerably alter SSCC pathways.
Bibliography:https://doi.org/10.1039/d3cc05389j
Electronic supplementary information (ESI) available: All calculation details, including Cartesian coordinates, benchmark studies of energies and SSCCs are available in the ESI. See DOI
ISSN:1359-7345
1364-548X
DOI:10.1039/d3cc05389j