Experimental and theoretical study of the ethoxy group conformational effect on 13C chemical shifts in Ortho-substituted phenetols

DG Kowalewski, VJ Kowalewski, Edith Botek, RH Contreras, JC Facelli

    Research output: Contribution to journalArticle

    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.
    Original languageEnglish
    Pages (from-to)351-356
    JournalMagnetic Resonance in Chemistry
    Volume35
    Issue number6
    DOIs
    Publication statusPublished - 1997

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