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The Weak Hydrogen Bond: Applications to Structural Chemistry and Biology(International Union of Crystallography Monographs on Crystallography, 9). By Gautam R. Desiraju
Molecules 1999, 4(11), 320-328; doi:10.3390/41100320
Article

17O NMR Spectra of α,β-Unsaturated Carbonyl Compounds RCH=CHCOX: the Influence of Group X on the δ(17O) Value of the Carbonyl Oxygen and on the Shielding Effect of Group R

College of Pharmacy, The Ohio State University, 500 West 12th Avenue, Columbus, OH 43210, USA
Received: 25 August 1999 / Accepted: 12 September 1999 / Published: 26 October 1999
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Abstract

17O NMR spectra of RCOX (R = Me, Ph), RCH=CHCOX (R = H, Ph, Me, CO2Et) and Me2C=CHCOX (X = H, Me, Et, i-Pr, t-Bu, Ph, PhCH=CH, OMe, OEt, Cl, CN, CF3, CO2Et) are reported. The 17O shift values of these carbonyl compounds depend mainly on the electron donating power of X and correlate well with the resonance constants sR+ of X. This suggests that the d(17O) values can be used to reflect qualitatively the electrophilicity of the carbonyl group. The shielding effect of the substituent R in RCH=CHCOX is diminished with increasing the electronic donating power of X and correlates with s+ values of X.
Keywords: 17O NMR; carbonyl groups; a; b-unsaturated carbonyl compounds; resonance effects 17O NMR; carbonyl groups; a; b-unsaturated carbonyl compounds; resonance effects
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Zhuo, J.-C. 17O NMR Spectra of α,β-Unsaturated Carbonyl Compounds RCH=CHCOX: the Influence of Group X on the δ(17O) Value of the Carbonyl Oxygen and on the Shielding Effect of Group R. Molecules 1999, 4, 320-328.

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