Journal of Organic Chemistry 2009-11-20

Solution structure of succinylacetone, an unsymmetrical beta-diketone, as studied by 13C NMR and GIAO-DFT calculations.

Dominika Bal, Anna Kraska-Dziadecka, Adam Gryff-Keller

文献索引：J. Org. Chem. 74(22) , 8604-9, (2009)

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摘要

The enolization degrees of succinylacetone, an important heme biosynthesis inhibitor, have been determined in CDCl(3) and water solutions using (1)H NMR. The solution structures of SA have been investigated using a combined NMR/theoretical [GIAO DFT PBE1PBE/6-311++G(2d, p) PCM] approach. The populations of both enolic forms undergoing enol-enol equilibriums for SA and a series of unsymmetrical beta-diketones have been established by a quantitative comparison of the experimental (13)C NMR chemical shifts and calculated shielding constants. Moreover, using the same method and considering various trial structures differing in conformation and/or hydration of neutral SA molecule as well as its monoanion and dianion the structures of the most abundant species being present in the investigated water solutions have been deduced.