Inducing proton tunnelling to increase the reactivity of boronic acids towards diols: A quantum biology study
Document Type
Article
Publication Date
1-15-2021
Abstract
Designing an efficient saccharide sensor in aqueous solution is an ongoing endeavour. Even though using hydrogen bonding groups on the sensor sounds like an efficient way for targeting the saccharides, it might lack accuracy due to the possibility of interaction with the solvent molecules. Boronic acid based sensors on the other hand, covalently and reversibly bind to saccharides with high sensitivity in aqueous medium. Many attempts are done to understand the mechanism of boronic acid's reaction with diols. However, the binding affinity of fructose cannot be clearly identified in such attempts. This study employs a novel computational approach to increase both reactivity and selectivity of boronic acid towards diols. Using DFT, five different electronegative R groups are simulated to calculate boronic acid's reactivity towards diol by adding the tunnelling effect to the calculations, where higher electronegative R-groups reduce the proton donor-acceptor distance that induces proton tunnelling and increases the reaction rate.
Keywords
Proton tunnelling, Boronic acid based sensors, Density Functional Theory, Proton transfer reaction
Divisions
Science
Funders
University of Malaya Fundamental Research Grant Scheme (FRGS) (FP047-2016)
Publication Title
Computational and Theoretical Chemistry
Volume
1194
Publisher
Elsevier
Publisher Location
RADARWEG 29, 1043 NX AMSTERDAM, NETHERLANDS