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Vibrational spectroscopy and conformations of 2,2-diacylethenamines

AuthorsGómez-Sánchez, Antonio; García Martín, Mª. de Gracia; Borrachero, Pastora; Bellanato, Juana
Issue Date1987
PublisherRoyal Society of Chemistry (UK)
CitationJournal of the Chemical Society, Perkin Transactions 2: 301-306 (1987)
AbstractThe i.r., Raman, and 1H n.m.r. spectra of 2,2- diacetylethenamines (3) and 2-aminomethylene-5,5-dimethylcyclohexane-1,3-diones (4) show that these substances exist exclusively in the chelated enamino-diketone form, and that the conjugated system contained in them is essentially planar. The open-chain enamino-diketones (3) exist either in the solid state or in solution in the EZE-conformation (7). A similar conjugated core, having the fixed ZZE-conformation, contained in 5-aminomethylene-2,2- dimethyl-1,3-dioxane-4,6-diones (5) is most probably planar or nearly planar. The EZE- and ZZE-alignments of the enamino-diketones can be distinguished by their spectral properties, and, particularly, by their vibrational spectra. Some features of the i.r. and Raman spectra indicate vibrational coupling between the two v(C=O) vibrations, the effect being more marked in the cyclic enamino-diketones (4) and -diesters (5) than in their open-chain analogues. On the other hand, the coupling of the v(C=O) with the v(C=C) and the δ(N-H) modes seems to be less efficient in these enaminodione systems than in the related simple enaninones. Further arguments are presented questioning the criteria established to ascertain the planarity of enamino-diones and of other enamines having two strong electron-acceptor groups at C-2.
Identifiersdoi: 10.1039/P29870000301
issn: 1472-779X
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