Please use this identifier to cite or link to this item: https://scidar.kg.ac.rs/handle/123456789/8499
Title: Acetophenone Mannich bases: Study of ionic liquid catalysed synthesis and antioxidative potential of products
Authors: Petrović, Vladimir
Simijonović, Dušica
Milovanović, Vesna
Petrović, Zorica
Journal: Royal Society Open Science
Issue Date: 1-Nov-2018
Abstract: © 2018 The Authors. Published by the Royal Society under the terms of the Creative Commons Attribution License Three-component Mannich reaction of acetophenone or 4-iodoacetophenone with a variety of substituted anilines and benzaldehyde, catalysed with diethanolammonium chloroacetate, was performed under mild conditions. Mannich bases (MBs), of which five are new, were obtained in good to excellent yields. All compounds were characterized using elemental analysis, NMR and IR. In addition, detailed experimental and simulated UV–Vis spectral characterization of these compounds is presented here for the first time. In vitro antioxidative potential of synthetized MBs was evaluated using 2,2-diphenyl-1-picryl-hydrazyl radical and density functional theory (DFT) thermodynamical study. It was shown that compounds with anisidine moiety express moderate antioxidative activity. Mechanism of the organocatalysed Mannich reaction was thoroughly inspected by means of DFT. The reaction undergoes the hydrogen bonding-assisted mechanism. Moreover, the proposed rate determining step of the overall reaction is water elimination in the process of iminium ion formation. To the extent of our knowledge, this is the first detailed report on the influence of this type of catalyst on the formation of iminium ion, as a crucial intermediate for the whole reaction.
URI: https://scidar.kg.ac.rs/handle/123456789/8499
Type: article
DOI: 10.1098/rsos.181232
SCOPUS: 85058407699
Appears in Collections:Faculty of Science, Kragujevac
Institute for Information Technologies, Kragujevac

Page views(s)

77

Downloads(s)

2

Files in This Item:
File Description SizeFormat 
10.1098-rsos.181232.pdf971.21 kBAdobe PDFThumbnail
View/Open


Items in SCIDAR are protected by copyright, with all rights reserved, unless otherwise indicated.