[en] The guanidine catalysed aminolysis of propylene carbonate has been investigated using the density functional theory (DFT) and highlights that different reaction pathways are involved depending on the aromatic or aliphatic nature of the amine. The structural ability of 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) to simultaneously give and receive protons was demonstrated by a detailed mechanistic investigation. The bifunctional activity (base/H-bond donor) of TBD significantly reduces the Gibbs energy of the reaction and allows understanding its higher efficiency compared to its methyl counterpart (MTBD).
Research center :
Center for Education and Research on Macromolecules (CERM) CESAM Complex and Entangled Systems from Atoms to Materials (CESAM)
Disciplines :
Materials science & engineering Chemistry
Author, co-author :
Alves, Margot ; University of Liège - ULiège > Complex and Entangled Systems from Atoms to Materials (CESAM), Center for Education and Research on Macromolecules (CERM)
Méreau, Raphaël; University of Bordeaux, Institute of Molecular Sciences, France
Grignard, Bruno ; University of Liège - ULiège > Complex and Entangled Systems from Atoms to Materials (CESAM), Center for Education and Research on Macromolecules (CERM)
Detrembleur, Christophe ; University of Liège - ULiège > Complex and Entangled Systems from Atoms to Materials (CESAM), Center for Education and Research on Macromolecules (CERM)
Jérôme, Christine ; University of Liège - ULiège > Complex and Entangled Systems from Atoms to Materials (CESAM), Center for Education and Research on Macromolecules (CERM)
Tassaing, Thierry; University of Bordeaux, Institute of Molecular Sciences, France
Language :
English
Title :
DFT investigation of the reaction mechanism for the guanidine catalyzed ring-opening of cyclic carbonates by aromatic and alkyl-amines
Publication date :
31 March 2017
Journal title :
RSC Advances
eISSN :
2046-2069
Publisher :
Royal Society of Chemistry Publishing, Cambridge, United Kingdom
Volume :
7
Issue :
31
Pages :
18993-19001
Peer reviewed :
Peer Reviewed verified by ORBi
Name of the research project :
IDEX program CO2Green and Flycoat programs
Funders :
F.R.S.-FNRS - Fonds de la Recherche Scientifique [BE] BELSPO - Politique scientifique fédérale [BE] Université de Bordeaux [FR] The International Doctoral School IDS-Funmat Walloon region [BE] Conseil Général d'Aquitaine [FR]
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