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Inducing proton tunnelling to increase the reactivity of boronic acids towards diols: A quantum biology study

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 a...

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Main Authors: Monajemi, Hadieh, Zain, Sharifuddin M., Ishida, Toshimasa, Abdullah, Wan Ahmad Tajuddin Wan
Format: Article
Published: Elsevier 2021
Subjects:
QC Physics
QD Chemistry
Online Access:http://eprints.um.edu.my/26543/
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spelling my.um.eprints.265432022-03-16T05:06:12Z http://eprints.um.edu.my/26543/ Inducing proton tunnelling to increase the reactivity of boronic acids towards diols: A quantum biology study Monajemi, Hadieh Zain, Sharifuddin M. Ishida, Toshimasa Abdullah, Wan Ahmad Tajuddin Wan QC Physics QD Chemistry 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. Elsevier 2021-01-15 Article PeerReviewed Monajemi, Hadieh and Zain, Sharifuddin M. and Ishida, Toshimasa and Abdullah, Wan Ahmad Tajuddin Wan (2021) Inducing proton tunnelling to increase the reactivity of boronic acids towards diols: A quantum biology study. Computational and Theoretical Chemistry, 1194. ISSN 2210-271X, DOI https://doi.org/10.1016/j.comptc.2020.113076 <https://doi.org/10.1016/j.comptc.2020.113076>. 10.1016/j.comptc.2020.113076
institution Universiti Malaya
building UM Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Universiti Malaya
content_source UM Research Repository
url_provider http://eprints.um.edu.my/
topic QC Physics
QD Chemistry
spellingShingle QC Physics
QD Chemistry
Monajemi, Hadieh
Zain, Sharifuddin M.
Ishida, Toshimasa
Abdullah, Wan Ahmad Tajuddin Wan
Inducing proton tunnelling to increase the reactivity of boronic acids towards diols: A quantum biology study
description 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.
format Article
author Monajemi, Hadieh
Zain, Sharifuddin M.
Ishida, Toshimasa
Abdullah, Wan Ahmad Tajuddin Wan
author_facet Monajemi, Hadieh
Zain, Sharifuddin M.
Ishida, Toshimasa
Abdullah, Wan Ahmad Tajuddin Wan
author_sort Monajemi, Hadieh
title Inducing proton tunnelling to increase the reactivity of boronic acids towards diols: A quantum biology study
title_short Inducing proton tunnelling to increase the reactivity of boronic acids towards diols: A quantum biology study
title_full Inducing proton tunnelling to increase the reactivity of boronic acids towards diols: A quantum biology study
title_fullStr Inducing proton tunnelling to increase the reactivity of boronic acids towards diols: A quantum biology study
title_full_unstemmed Inducing proton tunnelling to increase the reactivity of boronic acids towards diols: A quantum biology study
title_sort inducing proton tunnelling to increase the reactivity of boronic acids towards diols: a quantum biology study
publisher Elsevier
publishDate 2021
url http://eprints.um.edu.my/26543/
_version_ 1735409426346541056
score 13.211869

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