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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

Jin-Cong Zhuo

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

Download PDF Full-Text [61 KB, uploaded 10 October 2008 11:57 CEST]

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 s_R⁺ 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

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