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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

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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

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.

AMA Style

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(11):320-328.

Chicago/Turabian Style

Zhuo, Jin-Cong. 1999. "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 4, no. 11: 320-328.


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