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The Strong β−CF 3 Shielding Effect in Hexafluoroisopropanol and 100 Other Organic Solvents Revisited with 17 O NMR Spectroscopy
Author(s) -
Bernhardt Annika,
Kelm Harald,
Patureau Frederic W.
Publication year - 2018
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201701721
Subject(s) - trifluoroacetic acid , substituent , chemistry , nuclear magnetic resonance spectroscopy , spectroscopy , electromagnetic shielding , inorganic chemistry , medicinal chemistry , organic chemistry , materials science , quantum mechanics , composite material , physics
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.