Issue 31, 2017, Issue in Progress

DFT investigation of the reaction mechanism for the guanidine catalysed ring-opening of cyclic carbonates by aromatic and alkyl-amines

Abstract

The guanidine catalysed aminolysis of propylene carbonate has been investigated using 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 of its higher efficiency compared to its methyl counterpart (MTBD).

Graphical abstract: DFT investigation of the reaction mechanism for the guanidine catalysed ring-opening of cyclic carbonates by aromatic and alkyl-amines

Supplementary files

Article information

Article type
Paper
Submitted
06 Jan 2017
Accepted
23 Mar 2017
First published
31 Mar 2017
This article is Open Access
Creative Commons BY license

RSC Adv., 2017,7, 18993-19001

DFT investigation of the reaction mechanism for the guanidine catalysed ring-opening of cyclic carbonates by aromatic and alkyl-amines

M. Alves, R. Méreau, B. Grignard, C. Detrembleur, C. Jérôme and T. Tassaing, RSC Adv., 2017, 7, 18993 DOI: 10.1039/C7RA00220C

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