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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Published in | Chemical communications (Cambridge, England) Vol. 59; no. 99; pp. 14661 - 14664 |
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Main Authors | , , , , |
Format | Journal Article |
Published |
12.12.2023
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Online Access | Get full text |
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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
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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. |
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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 |