STUDIES OF MERCURATED DERIVATIVES OF ACETYLACETONE AND ETHYL ACETOACETATE BY SOLID-STATE NUCLEAR-MAGNETIC-RESONANCE AND VIBRATIONAL SPECTROSCOPIES

Seven new mono- and/or dimercurated compounds involving acetylacetone (2,4-pentanedione) or ethyl acetoacetate (3-ethyl ketobutanoate) were synthesized in aqueous medium. In all cases, mercuration occurred at methylene carbon atoms. All compounds were carefully analyzed by solid state carbon-13 nuclear magnetic resonance. Assignments were confirmed by using selective sequences, which allowed a total editing of the spectra. It was shown that deshielding of C-13 mercurated sites occurred when the rate of mercuration increased. It was also possible to measure direct (1)J((HgC)-Hg-199-C-13) coupling constants. The main bands of the vibrational spectra (infrared and Raman) were assigned. It was proved that nu(C=O) and delta(C(gamma)-H) could be directly related to the mercuration rate of molecules.