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Theoretical study of anion carriers based on trifluoroacetophenone

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Abstract

Model calculations on anion carrier ligands related to trifluoroacetophenone were carried out using the semiempirical AM 1 method in order to investigate the factors involved in such anion-ligand complexation. The reaction of halogen derivatives of acetophenone with various nucleophiles such as water, carbonic acid, and bicarbonate anion was studied. By this means, the effect of various structural changes, such as variation of the ring substituents and variation of the degree and type of halogen atom substitution, could be determined. It is shown that in terms of relative stability, fluorine derivatives are preferable to chlorine derivatives for the binding of water and carbonic acid. Monosubstitution of a methoxy group in the ortho position of the trifluoroacetophenone ring also brought about stability in the case of the hydration reaction. An electron-withdrawing ester group in the para position on the trifluoroacetophenone ring brings about stabilization also.

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Correspondence to Janice M. Inglis.

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Inglis, J.M., Ha, T. Theoretical study of anion carriers based on trifluoroacetophenone. Struct Chem 8, 109–119 (1997). https://doi.org/10.1007/BF02262846

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Key words

  • AM1
  • trifluoroacetophenone
  • semiempirical
  • anion carrier ligands