Optimization and a Kinetic Study on the Acidic Hydrolysis of Dialkyl α-Hydroxybenzylphosphonates

The two-step acidic hydrolysis of α-hydroxybenzylphosphonates and a few related derivatives was monitored in order to determine the kinetics and to map the reactivity of the differently substituted phosphonates in hydrolysis. Electron-withdrawing substituents increased the rate, while electron-relea...

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Autores principales: Harsági, Nikoletta, Rádai, Zita, Szigetvári, Áron, Kóti, János, Keglevich, György
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2020
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7504060/
https://www.ncbi.nlm.nih.gov/pubmed/32825450
http://dx.doi.org/10.3390/molecules25173793
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author Harsági, Nikoletta
Rádai, Zita
Szigetvári, Áron
Kóti, János
Keglevich, György
author_facet Harsági, Nikoletta
Rádai, Zita
Szigetvári, Áron
Kóti, János
Keglevich, György
author_sort Harsági, Nikoletta
collection PubMed
description The two-step acidic hydrolysis of α-hydroxybenzylphosphonates and a few related derivatives was monitored in order to determine the kinetics and to map the reactivity of the differently substituted phosphonates in hydrolysis. Electron-withdrawing substituents increased the rate, while electron-releasing ones slowed down the reaction. Both hydrolysis steps were characterized by pseudo-first-order rate constants. The fission of the second P-O-C bond was found to be the rate-determining step.
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spelling pubmed-75040602020-09-24 Optimization and a Kinetic Study on the Acidic Hydrolysis of Dialkyl α-Hydroxybenzylphosphonates Harsági, Nikoletta Rádai, Zita Szigetvári, Áron Kóti, János Keglevich, György Molecules Article The two-step acidic hydrolysis of α-hydroxybenzylphosphonates and a few related derivatives was monitored in order to determine the kinetics and to map the reactivity of the differently substituted phosphonates in hydrolysis. Electron-withdrawing substituents increased the rate, while electron-releasing ones slowed down the reaction. Both hydrolysis steps were characterized by pseudo-first-order rate constants. The fission of the second P-O-C bond was found to be the rate-determining step. MDPI 2020-08-20 /pmc/articles/PMC7504060/ /pubmed/32825450 http://dx.doi.org/10.3390/molecules25173793 Text en © 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Harsági, Nikoletta
Rádai, Zita
Szigetvári, Áron
Kóti, János
Keglevich, György
Optimization and a Kinetic Study on the Acidic Hydrolysis of Dialkyl α-Hydroxybenzylphosphonates
title Optimization and a Kinetic Study on the Acidic Hydrolysis of Dialkyl α-Hydroxybenzylphosphonates
title_full Optimization and a Kinetic Study on the Acidic Hydrolysis of Dialkyl α-Hydroxybenzylphosphonates
title_fullStr Optimization and a Kinetic Study on the Acidic Hydrolysis of Dialkyl α-Hydroxybenzylphosphonates
title_full_unstemmed Optimization and a Kinetic Study on the Acidic Hydrolysis of Dialkyl α-Hydroxybenzylphosphonates
title_short Optimization and a Kinetic Study on the Acidic Hydrolysis of Dialkyl α-Hydroxybenzylphosphonates
title_sort optimization and a kinetic study on the acidic hydrolysis of dialkyl α-hydroxybenzylphosphonates
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7504060/
https://www.ncbi.nlm.nih.gov/pubmed/32825450
http://dx.doi.org/10.3390/molecules25173793
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