Figure 1: Positioning and stabilization of enolate anions on π-acidic surfaces. | Nature Communications

Figure 1: Positioning and stabilization of enolate anions on π-acidic surfaces.

From: Enolate chemistry with anion–π interactions

Figure 1

1H-NMR spectra of a 1:1 mixture of 1 (blue H at 3.38 p.p.m.) and 5 (red H at 1.60 p.p.m.) in CDCl3 in the presence of increasing amounts of TMG (from bottom to top, 0.5, 1, 5, 10, 15, 20, 30, 40 and 50 equivalents) reveal that 5 is ΔpKa=1.9 more acidic than 1, that is, a stabilization of the enolate anion on the π-acidic surface of 5 by ΔΔG=4.7 kJ mol−1 (R=H).

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