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      α-Halogenoacetanilides as hydrogen-bonding organocatalysts that activate carbonyl bonds: fluorine versus chlorine and bromine.

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          Abstract

          α-Halogenoacetanilides (X=F, Cl, Br) were examined as H-bonding organocatalysts designed for the double activation of CO bonds through NH and CH donor groups. Depending on the halide substituents, the double H-bond involved a nonconventional CH⋅⋅⋅O interaction with either a HCXn (n=1-2, X=Cl, Br) or a HCAr bond (X=F), as shown in the solid-state crystal structures and by molecular modeling. In addition, the catalytic properties of α-halogenoacetanilides were evaluated in the ring-opening polymerization of lactide, in the presence of a tertiary amine as cocatalyst. The α-dichloro- and α-dibromoacetanilides containing electron-deficient aromatic groups afforded the most attractive double H-bonding properties towards CO bonds, with a NH⋅⋅⋅O⋅⋅⋅HCX2 interaction.

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          Author and article information

          Journal
          Chemistry
          Chemistry (Weinheim an der Bergstrasse, Germany)
          1521-3765
          0947-6539
          Mar 3 2014
          : 20
          : 10
          Affiliations
          [1 ] Institut des Sciences Moléculaires, UMR CNRS 5255, Université de Bordeaux, 351 cours de la Libération, 33405 Talence (France), Fax: (+33) 54000-6158.
          Article
          10.1002/chem.201303662
          24519659
          af219a39-af60-43e6-9912-9b690616f069
          © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
          History

          hydrogen bonds,lactide,noncovalent interactions,organocatalysis,ring-opening polymerization

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