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17O NMR Spectra of Carbonyl Compounds ArCOX: Influence of Groups X on the Polarity of the Carbonyl Group

✍ Scribed by Hans Dahn; Peter Péchy; Vien Van Toan

Publisher: John Wiley and Sons
Year: 1997
Tongue: English
Weight: 236 KB
Volume: 35
Category: Article
ISSN: 0749-1581
DOI: 10.1002/(sici)1097-458x(199709)35:9<589::aid-omr134>3.0.co;2-l

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✦ Synopsis

The 17O shift values of para-substituted benzoyl compounds (X = H, COOEt, Br, Cl, F, p-YC 6 H 4 COX CF 3 , SEt, OCOAr, OH, O-Na', were measured. The 17O shielding values d(17O) of these and other aryl-NH 2 ) unsubstituted benzoyl compounds (Y = H) follow the electron-donating power of X (resonance), whereas inductive electron attractors COOEt) show only small e †ects. The sensitivity of the shift values to donor/attractor (CF 3

, para substituents Y, measured as the Hammett-Taft q' = d(17O)/r', follows both the resonance and the inductive e †ects ; combined with the d(17O) values, it is proposed as an empirical measure of the polarity (electrophilicity) of the carbonyl group (35 types of COX in Table ).

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