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Title: Assessing the pK <inf>a</inf> -Dependent Activity of Hydroxyl Hydrogen Bond Donors in the Organocatalyzed Cycloaddition of Carbon Dioxide to Epoxides: Experimental and Theoretical Study
Authors: Prapussorn Yingcharoen
Chutima Kongtes
Sunatda Arayachukiat
Kittipong Suvarnapunya
Sai V.C. Vummaleti
Sippakorn Wannakao
Luigi Cavallo
Albert Poater
Valerio D' Elia
Vidyasirimedhi Institute of Science and Technology
King Abdullah University of Science and Technology
Faculty of Medicine, Siriraj Hospital, Mahidol University
Universitat de Girona
Keywords: Chemical Engineering;Chemistry
Issue Date: 22-Jan-2019
Citation: Advanced Synthesis and Catalysis. Vol.361, No.2 (2019), 366-373
Abstract: © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim The development of hydrogen bond donors (HBDs) as catalytic moieties in the cycloaddition of carbon dioxide to epoxides is an active field of research to access efficient, inexpensive and sustainable metal-free systems for the conversion of carbon dioxide to useful chemicals. Thus far, no systematic attempt to correlate the activity of a diverse selection of HBDs to their physico-chemical properties has been undertaken. In this work, we investigate factors influencing the catalytic activity of hydroxyl HBDs from different chemical families under ambient conditions by considering the HBDs Brønsted acidity (expressed as pK a ), the number of hydroxyls and structural aspects. As an effect, this study highlights the crucial role of the hydroxyl protons’ Brønsted acidity in determining the catalytic activity of the HBDs, identifies an ideal range for the hydroxyl HBDs proton acidity (9 <pK a <11) and leads to a revaluation of phenol and to the discovery of a simple ascorbic acid derivative as efficient HBDs for the title cycloaddition reaction. Density functional theory (DFT) calculations show mild reactions barriers for the reaction catalysed by phenol and suggest the occurrence of aggregation between molecules of ascorbic acid as a further factor affecting catalytic activity. (Figure presented.).
ISSN: 16154169
Appears in Collections:Scopus 2019

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