The Strong β−CF(3) Shielding Effect in Hexafluoroisopropanol and 100 Other Organic Solvents Revisited with (17)O NMR Spectroscopy

An (17)O NMR spectroscopy survey of more than 100 ubiquitous organic solvents and compounds, including some typical oxofluorinated solvents such as hexafluoroisopropanol, trifluoroethanol, trifluoroacetic acid, and others, is presented with D(2)O as a reference. A strong alternating α,β−CF(3)‐substi...

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Detalles Bibliográficos
Autores principales: Bernhardt, Annika, Kelm, Harald, Patureau, Frederic W.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2018
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5915748/
https://www.ncbi.nlm.nih.gov/pubmed/29731952
http://dx.doi.org/10.1002/cctc.201701721
Descripción
Sumario:An (17)O NMR spectroscopy survey of more than 100 ubiquitous organic solvents and compounds, including some typical oxofluorinated solvents such as hexafluoroisopropanol, trifluoroethanol, trifluoroacetic acid, and others, is presented with D(2)O as a reference. A strong alternating α,β−CF(3)‐substituent chemical shift effect was thus observed. This alternating deshielding–shielding effect is suspected to have a role in the exceptional properties of these oxofluorinated solvents, notably in oxidative cross‐coupling reactions.

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