α-Halogenoacetanilides as hydrogen-bonding organocatalysts that activate carbonyl bonds: fluorine versus chlorine and bromine
THOMAS, Coralie
Institut des Sciences Moléculaires [ISM]
Laboratoire de Chimie des Polymères Organiques [LCPO]
Institut des Sciences Moléculaires [ISM]
Laboratoire de Chimie des Polymères Organiques [LCPO]
PERUCH, Frédéric
Laboratoire de Chimie des Polymères Organiques [LCPO]
Team 1 LCPO : Polymerization Catalyses & Engineering
See more >
Laboratoire de Chimie des Polymères Organiques [LCPO]
Team 1 LCPO : Polymerization Catalyses & Engineering
THOMAS, Coralie
Institut des Sciences Moléculaires [ISM]
Laboratoire de Chimie des Polymères Organiques [LCPO]
Institut des Sciences Moléculaires [ISM]
Laboratoire de Chimie des Polymères Organiques [LCPO]
PERUCH, Frédéric
Laboratoire de Chimie des Polymères Organiques [LCPO]
Team 1 LCPO : Polymerization Catalyses & Engineering
Laboratoire de Chimie des Polymères Organiques [LCPO]
Team 1 LCPO : Polymerization Catalyses & Engineering
DEFFIEUX, Alain
Laboratoire de Chimie des Polymères Organiques [LCPO]
Team 1 LCPO : Polymerization Catalyses & Engineering
< Reduce
Laboratoire de Chimie des Polymères Organiques [LCPO]
Team 1 LCPO : Polymerization Catalyses & Engineering
Language
en
Article de revue
This item was published in
Chemistry - A European Journal. 2014, vol. 20, n° 10, p. 2849-2859
Wiley-VCH Verlag
English Abstract
α-Halogenoacetanilides (X=F, Cl, Br) were examined as H-bonding organocatalysts designed for the double activation of CO bonds through NH and CH donor groups. Depending on the halide substituents, the double H-bond involved ...Read more >
α-Halogenoacetanilides (X=F, Cl, Br) were examined as H-bonding organocatalysts designed for the double activation of CO bonds through NH and CH donor groups. Depending on the halide substituents, the double H-bond involved a nonconventional CH⋅⋅⋅O interaction with either a HCXn (n=1-2, X=Cl, Br) or a HCAr 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 CO bonds, with a NH⋅⋅⋅O⋅⋅⋅HCX2 interaction. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, WeinheimRead less <
English Keywords
Hydrocarbons
Bromine
Acetanilides
hydrogen bond
chemistry
chemical structure
halogenated hydrocarbon
fluoride
acetanilide derivative
ring-opening polymerization
Fluorine
Catalysis
Chlorine
Fluorides
hydrogen bonds
lactide
noncovalent interactions
organocatalysis
Halogenated
Hydrogen Bonding
Models
Molecular
Quantum Theory
Origin
Hal imported