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The possibilities and limitations of 13C NMR spectroscopy for the determination of the basicity of carbonyl-containing compounds are examined.It is shown that the protonation of polycyclic aromatic ketones in deutero acids increases the contribition of the C+-OD form relative to that of the C=+OD form, whereas in the case of aliphatic ketones and of monosubstituted acetophenones and benzaldehydes the C=+OD form is predominant.
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Reference：
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate