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Molecules 1997, 2(2), 31-35; doi:10.3390/feb97p1

17O NMR of Enamino-Diesters: Intramolecular Hydrogen Bonding in 5-Alkylaminomethylene-2,2-dimethyl-1,3-dioxane-4,6-diones

Institute of Organic Chemistry, University of Lausanne, BCH, CH-1015, Lausanne-Dorigny, Switzerland
Received: 20 December 1996 / Accepted: 17 January 1997 / Published: 25 February 1997
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Natural abundance 17O NMR spectra of a series of 5-alkylaminomethylene-2,2-dimethyl-1,3-dioxane-4,6-diones, recorded in acetonitrile solution, are reported. The δ(17O) values correlate well with those of 4-alkylaminobut-3-en-2-ones and with the pKa values of amines. The effects of the N-alkyl groups on the 17O shift values is diminished, owing to the resonance effects of the alkoxy groups. The shift difference (DδHB) between the two carbonyl groups is mainly attributed to the intramolecular hydrogen bonding and depends on the donor property of the amino group.
Keywords: NMR; 17O NMR; enamino-diesters; intramolecular hydrogen bonding NMR; 17O NMR; enamino-diesters; intramolecular hydrogen bonding
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Zhuo, J.-C. 17O NMR of Enamino-Diesters: Intramolecular Hydrogen Bonding in 5-Alkylaminomethylene-2,2-dimethyl-1,3-dioxane-4,6-diones. Molecules 1997, 2, 31-35.

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