α-Halogenoacetanilides as hydrogen-bonding organocatalysts that activate carbonyl bonds: fluorine versus chlorine and bromine
| dc.rights.license | open | |
| hal.structure.identifier | Institut des Sciences Moléculaires [ISM] | |
| dc.contributor.author | KOELLER, Sylvain | |
| hal.structure.identifier | Institut des Sciences Moléculaires [ISM] | |
| hal.structure.identifier | Laboratoire de Chimie des Polymères Organiques [LCPO] | |
| dc.contributor.author | THOMAS, Coralie | |
| hal.structure.identifier | Laboratoire de Chimie des Polymères Organiques [LCPO] | |
| hal.structure.identifier | Team 1 LCPO : Polymerization Catalyses & Engineering | |
| dc.contributor.author | PERUCH, Frédéric
IDREF: 152900748 | |
| hal.structure.identifier | Laboratoire de Chimie des Polymères Organiques [LCPO] | |
| hal.structure.identifier | Team 1 LCPO : Polymerization Catalyses & Engineering | |
| dc.contributor.author | DEFFIEUX, Alain | |
| dc.contributor.author | MASSIP, Stéphane | |
| dc.contributor.author | LÉGER, Jean-Michel | |
| hal.structure.identifier | Institut des Sciences Moléculaires [ISM] | |
| dc.contributor.author | DESVERGNE, Jean-Pierre | |
| hal.structure.identifier | Département de Chimie Moléculaire - Chimie Théorique [DCM - CT] | |
| dc.contributor.author | MILET, Anne | |
| hal.structure.identifier | Institut des Sciences Moléculaires [ISM] | |
| dc.contributor.author | BIBAL, Brigitte | |
| dc.date.accessioned | 2020 | |
| dc.date.available | 2020 | |
| dc.date.issued | 2014 | |
| dc.identifier.issn | 0947-6539 | |
| dc.identifier.uri | https://oskar-bordeaux.fr/handle/20.500.12278/20228 | |
| dc.description.abstractEn | 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, Weinheim | |
| dc.language.iso | en | |
| dc.publisher | Wiley-VCH Verlag | |
| dc.subject.en | Hydrocarbons | |
| dc.subject.en | Bromine | |
| dc.subject.en | Acetanilides | |
| dc.subject.en | hydrogen bond | |
| dc.subject.en | chemistry | |
| dc.subject.en | chemical structure | |
| dc.subject.en | halogenated hydrocarbon | |
| dc.subject.en | fluoride | |
| dc.subject.en | acetanilide derivative | |
| dc.subject.en | ring-opening polymerization | |
| dc.subject.en | Fluorine | |
| dc.subject.en | Catalysis | |
| dc.subject.en | Chlorine | |
| dc.subject.en | Fluorides | |
| dc.subject.en | hydrogen bonds | |
| dc.subject.en | lactide | |
| dc.subject.en | noncovalent interactions | |
| dc.subject.en | organocatalysis | |
| dc.subject.en | Halogenated | |
| dc.subject.en | Hydrogen Bonding | |
| dc.subject.en | Models | |
| dc.subject.en | Molecular | |
| dc.subject.en | Quantum Theory | |
| dc.title.en | α-Halogenoacetanilides as hydrogen-bonding organocatalysts that activate carbonyl bonds: fluorine versus chlorine and bromine | |
| dc.type | Article de revue | |
| dc.identifier.doi | 10.1002/chem.201303662 | |
| dc.subject.hal | Chimie/Polymères | |
| bordeaux.journal | Chemistry - A European Journal | |
| bordeaux.page | 2849-2859 | |
| bordeaux.volume | 20 | |
| bordeaux.hal.laboratories | Laboratoire de Chimie des Polymères Organiques (LCPO) - UMR 5629 | * |
| bordeaux.issue | 10 | |
| bordeaux.institution | Bordeaux INP | |
| bordeaux.institution | Université de Bordeaux | |
| bordeaux.peerReviewed | oui | |
| hal.identifier | hal-01368968 | |
| hal.version | 1 | |
| hal.origin.link | https://hal.archives-ouvertes.fr//hal-01368968v1 | |
| bordeaux.COinS | ctx_ver=Z39.88-2004&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.jtitle=Chemistry%20-%20A%20European%20Journal&rft.date=2014&rft.volume=20&rft.issue=10&rft.spage=2849-2859&rft.epage=2849-2859&rft.eissn=0947-6539&rft.issn=0947-6539&rft.au=KOELLER,%20Sylvain&THOMAS,%20Coralie&PERUCH,%20Fr%C3%A9d%C3%A9ric&DEFFIEUX,%20Alain&MASSIP,%20St%C3%A9phane&rft.genre=article |
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