D. de Kowalewski, V. Kowalewski, E. Botek
Jun 1, 1997
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Journal
Magnetic Resonance in Chemistry
Abstract
The 13C chemical shifts of nine 2‐X‐substituted phenetol derivatives were measured together with the 13C chemical shifts of the corresponding X‐monosubstituted benzenes. Using an additivity scheme, the ethoxy cis‐ and trans‐ortho‐SCSs (substituent chemical shifts) at C‐6 and C‐2, respectively, were determined to be shielding effects of 16.5 and 10.9 ppm, respectively, which are close to those determined previously in anisole derivatives. Optimized geometries at the Hartree–Fock level employing a D95** basis set for three different phenetol conformers were obtained and the corresponding chemical shifts of all 13C nuclei were calculated using the same basis set and the CHF‐GIAO approach. Results are discussed in terms of different interactions defining different conformations, particularly that between a polar bond and a proximate highly polarizable one. © John Wiley & Sons, Ltd.