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17 O NMR Spectroscopy of Benzoyl Compounds YC 6 H 4 COX: Sensitivity to Ring Substituents as a Measure of the Electron Demand of the Carbonyl Group
Author(s) -
Dahn Hans,
Péchy Peter,
Van Toan Vien
Publication year - 1990
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199006471
Subject(s) - electrophile , ring (chemistry) , spectroscopy , chemistry , nuclear magnetic resonance spectroscopy , atom (system on chip) , crystallography , medicinal chemistry , stereochemistry , organic chemistry , catalysis , physics , quantum mechanics , computer science , embedded system
Contrary to the consensus of opinion 13 C‐NMR spectroscopy is not suitable for the determination of electron density at the carbonyl C‐atom. However, by measurement of the 17 O‐chemical shift in aromatic carbonyl compounds Y‐C 6 H 4 ‐COX, X = CF 3 , H, CH 3 , CO 2 R, Br, Cl, F, OCOAryl, SR, OR, NH 2 , OH, O ⊖ , reliable statements could be made about the electrophilicity of the carbonyl C‐atom. It is gratifying that the results are in agreement with classical chemical rules. There is much to be said for 17 O‐NMR spectroscopy being given more attention than hitherto.