Thermodynamic and Kinetic Study of Diels–Alder Reaction between Furfuryl Alcohol and <i>N</i>-Hydroxymaleimides—An Assessment for Materials Application
The study of Diels−Alder reactions in materials science is of increasing interest. The main reason for that is the potential thermoreversibility of the reaction. Aiming to predict the behavior of a material modified with maleimido and furyl moieties, <sup>1</sup>H NMR and UV-Vi...
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| Format: | Article |
| Language: | English |
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MDPI AG
2020-01-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/25/2/243 |
| _version_ | 1818137410523889664 |
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| author | Jamerson Carneiro de Oliveira Marie-Pierre Laborie Vincent Roucoules |
| author_facet | Jamerson Carneiro de Oliveira Marie-Pierre Laborie Vincent Roucoules |
| author_sort | Jamerson Carneiro de Oliveira |
| collection | DOAJ |
| description | The study of Diels−Alder reactions in materials science is of increasing interest. The main reason for that is the potential thermoreversibility of the reaction. Aiming to predict the behavior of a material modified with maleimido and furyl moieties, <sup>1</sup>H NMR and UV-Vis solution studies of the Diels−Alder reaction between furfuryl alcohol and two <i>N</i>-hydroxymaleimides are explored in the present study. Rate constants, activation energy, entropy, and enthalpy of formation were determined from each technique for both reacting systems. <i>Endo</i> and <i>exo</i> isomers were distinguished in <sup>1</sup>H NMR, and the transition from a kinetic, controlled Diels−Alder reaction to a thermodynamic one could be observed in the temperature range studied. A discussion on the effect of that on the application in a material was performed. The approach selected considers a simplified equilibrium of the Diels−Alder reaction as the kinetic model, allowing materials scientists to evaluate the suitability of using the reacting molecules for the creation of thermoresponsive materials. The proposed approach determines the kinetic constants without the direct influence of the equilibrium constant value, thereby allowing a more objective data analysis. The effects of the selection of kinetic model, analytical method, and data treatment are discussed. |
| first_indexed | 2024-12-11T09:55:52Z |
| format | Article |
| id | doaj.art-59db46be34e247fa845d6ca88c1e7562 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-11T09:55:52Z |
| publishDate | 2020-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-59db46be34e247fa845d6ca88c1e75622022-12-22T01:12:17ZengMDPI AGMolecules1420-30492020-01-0125224310.3390/molecules25020243molecules25020243Thermodynamic and Kinetic Study of Diels–Alder Reaction between Furfuryl Alcohol and <i>N</i>-Hydroxymaleimides—An Assessment for Materials ApplicationJamerson Carneiro de Oliveira0Marie-Pierre Laborie1Vincent Roucoules2Chair of Forest Biomaterials, Faculty of Environment and Natural Resources, University of Freiburg, 79085 Freiburg, GermanyChair of Forest Biomaterials, Faculty of Environment and Natural Resources, University of Freiburg, 79085 Freiburg, GermanyIS2M, UMR 7361, CNRS, Université de Haute-Alsace, Université de Strasbourg, F-68100 Mulhouse, FranceThe study of Diels−Alder reactions in materials science is of increasing interest. The main reason for that is the potential thermoreversibility of the reaction. Aiming to predict the behavior of a material modified with maleimido and furyl moieties, <sup>1</sup>H NMR and UV-Vis solution studies of the Diels−Alder reaction between furfuryl alcohol and two <i>N</i>-hydroxymaleimides are explored in the present study. Rate constants, activation energy, entropy, and enthalpy of formation were determined from each technique for both reacting systems. <i>Endo</i> and <i>exo</i> isomers were distinguished in <sup>1</sup>H NMR, and the transition from a kinetic, controlled Diels−Alder reaction to a thermodynamic one could be observed in the temperature range studied. A discussion on the effect of that on the application in a material was performed. The approach selected considers a simplified equilibrium of the Diels−Alder reaction as the kinetic model, allowing materials scientists to evaluate the suitability of using the reacting molecules for the creation of thermoresponsive materials. The proposed approach determines the kinetic constants without the direct influence of the equilibrium constant value, thereby allowing a more objective data analysis. The effects of the selection of kinetic model, analytical method, and data treatment are discussed.https://www.mdpi.com/1420-3049/25/2/243diels–aldermaterialskineticthermodynamic |
| spellingShingle | Jamerson Carneiro de Oliveira Marie-Pierre Laborie Vincent Roucoules Thermodynamic and Kinetic Study of Diels–Alder Reaction between Furfuryl Alcohol and <i>N</i>-Hydroxymaleimides—An Assessment for Materials Application Molecules diels–alder materials kinetic thermodynamic |
| title | Thermodynamic and Kinetic Study of Diels–Alder Reaction between Furfuryl Alcohol and <i>N</i>-Hydroxymaleimides—An Assessment for Materials Application |
| title_full | Thermodynamic and Kinetic Study of Diels–Alder Reaction between Furfuryl Alcohol and <i>N</i>-Hydroxymaleimides—An Assessment for Materials Application |
| title_fullStr | Thermodynamic and Kinetic Study of Diels–Alder Reaction between Furfuryl Alcohol and <i>N</i>-Hydroxymaleimides—An Assessment for Materials Application |
| title_full_unstemmed | Thermodynamic and Kinetic Study of Diels–Alder Reaction between Furfuryl Alcohol and <i>N</i>-Hydroxymaleimides—An Assessment for Materials Application |
| title_short | Thermodynamic and Kinetic Study of Diels–Alder Reaction between Furfuryl Alcohol and <i>N</i>-Hydroxymaleimides—An Assessment for Materials Application |
| title_sort | thermodynamic and kinetic study of diels alder reaction between furfuryl alcohol and i n i hydroxymaleimides an assessment for materials application |
| topic | diels–alder materials kinetic thermodynamic |
| url | https://www.mdpi.com/1420-3049/25/2/243 |
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