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...
| Main Authors: | , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2020-08-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/25/17/3793 |
| _version_ | 1797556629106851840 |
|---|---|
| author | Nikoletta Harsági Zita Rádai Áron Szigetvári János Kóti György Keglevich |
| author_facet | Nikoletta Harsági Zita Rádai Áron Szigetvári János Kóti György Keglevich |
| author_sort | Nikoletta Harsági |
| collection | DOAJ |
| 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. |
| first_indexed | 2024-03-10T17:05:33Z |
| format | Article |
| id | doaj.art-1982bb6ae4fa49e995902e6301de8508 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T17:05:33Z |
| publishDate | 2020-08-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-1982bb6ae4fa49e995902e6301de85082023-11-20T10:48:46ZengMDPI AGMolecules1420-30492020-08-012517379310.3390/molecules25173793Optimization and a Kinetic Study on the Acidic Hydrolysis of Dialkyl α-HydroxybenzylphosphonatesNikoletta Harsági0Zita Rádai1Áron Szigetvári2János Kóti3György Keglevich4Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, HungaryDepartment of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, HungaryGedeon Richter Plc., 1475 Budapest, HungaryGedeon Richter Plc., 1475 Budapest, HungaryDepartment of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, HungaryThe 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.https://www.mdpi.com/1420-3049/25/17/3793dialkyl α-hydroxyphosphonateshydrolysisphosphonic ester–acid intermediatephosphonic acidrate constantsmechanism |
| spellingShingle | Nikoletta Harsági Zita Rádai Áron Szigetvári János Kóti György Keglevich Optimization and a Kinetic Study on the Acidic Hydrolysis of Dialkyl α-Hydroxybenzylphosphonates Molecules dialkyl α-hydroxyphosphonates hydrolysis phosphonic ester–acid intermediate phosphonic acid rate constants mechanism |
| 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 | dialkyl α-hydroxyphosphonates hydrolysis phosphonic ester–acid intermediate phosphonic acid rate constants mechanism |
| url | https://www.mdpi.com/1420-3049/25/17/3793 |
| work_keys_str_mv | AT nikolettaharsagi optimizationandakineticstudyontheacidichydrolysisofdialkylahydroxybenzylphosphonates AT zitaradai optimizationandakineticstudyontheacidichydrolysisofdialkylahydroxybenzylphosphonates AT aronszigetvari optimizationandakineticstudyontheacidichydrolysisofdialkylahydroxybenzylphosphonates AT janoskoti optimizationandakineticstudyontheacidichydrolysisofdialkylahydroxybenzylphosphonates AT gyorgykeglevich optimizationandakineticstudyontheacidichydrolysisofdialkylahydroxybenzylphosphonates |