Thermochemistry of Solution, Solvation, and Hydrogen Bonding of Cyclic Amides in Proton Acceptor and Donor Solvents. Amide Cycle Size Effect
In the present work, the thermochemistry of solution, solvation, and hydrogen bonding of cyclic amides in proton acceptor (B) and proton donor (RXH) solvents were studied. The infinite dilution solution enthalpies of δ-valerolactam, <i>N</i>-methylvalerolactam, ε-caprolactam, and <i&g...
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| Format: | Article |
| Language: | English |
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MDPI AG
2021-03-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/26/5/1411 |
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| author | Ilnaz T. Rakipov Artem A. Petrov Aydar A. Akhmadiyarov Artashes A. Khachatrian Timur A. Mukhametzyanov Boris N. Solomonov |
| author_facet | Ilnaz T. Rakipov Artem A. Petrov Aydar A. Akhmadiyarov Artashes A. Khachatrian Timur A. Mukhametzyanov Boris N. Solomonov |
| author_sort | Ilnaz T. Rakipov |
| collection | DOAJ |
| description | In the present work, the thermochemistry of solution, solvation, and hydrogen bonding of cyclic amides in proton acceptor (B) and proton donor (RXH) solvents were studied. The infinite dilution solution enthalpies of δ-valerolactam, <i>N</i>-methylvalerolactam, ε-caprolactam, and <i>N</i>-methylcaprolactam were measured at 298.15 K. The solvation enthalpies of cyclic amides were calculated based on the measured solution enthalpies and sublimation/vaporization enthalpies from literature. The enthalpies of hydrogen bonding between cyclic amides and proton acceptor and donor solvents were then calculated as a difference between the total solvation enthalpy and the non-specific contribution. The latter was estimated via two different approaches in proton donor and proton accepting solvents. The effect of the cycle size on the strength of hydrogen bonding of the cyclic amides in solution is discussed. |
| first_indexed | 2024-03-09T05:19:35Z |
| format | Article |
| id | doaj.art-c5f98b5a38204cf49a6b4b23177e2268 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T05:19:35Z |
| publishDate | 2021-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-c5f98b5a38204cf49a6b4b23177e22682023-12-03T12:41:50ZengMDPI AGMolecules1420-30492021-03-01265141110.3390/molecules26051411Thermochemistry of Solution, Solvation, and Hydrogen Bonding of Cyclic Amides in Proton Acceptor and Donor Solvents. Amide Cycle Size EffectIlnaz T. Rakipov0Artem A. Petrov1Aydar A. Akhmadiyarov2Artashes A. Khachatrian3Timur A. Mukhametzyanov4Boris N. Solomonov5Department of Physical Chemistry, Kazan Federal University, Kremlevskaya 18, Kazan 420008, RussiaDepartment of Physical Chemistry, Kazan Federal University, Kremlevskaya 18, Kazan 420008, RussiaDepartment of Physical Chemistry, Kazan Federal University, Kremlevskaya 18, Kazan 420008, RussiaDepartment of Physical Chemistry, Kazan Federal University, Kremlevskaya 18, Kazan 420008, RussiaDepartment of Physical Chemistry, Kazan Federal University, Kremlevskaya 18, Kazan 420008, RussiaDepartment of Physical Chemistry, Kazan Federal University, Kremlevskaya 18, Kazan 420008, RussiaIn the present work, the thermochemistry of solution, solvation, and hydrogen bonding of cyclic amides in proton acceptor (B) and proton donor (RXH) solvents were studied. The infinite dilution solution enthalpies of δ-valerolactam, <i>N</i>-methylvalerolactam, ε-caprolactam, and <i>N</i>-methylcaprolactam were measured at 298.15 K. The solvation enthalpies of cyclic amides were calculated based on the measured solution enthalpies and sublimation/vaporization enthalpies from literature. The enthalpies of hydrogen bonding between cyclic amides and proton acceptor and donor solvents were then calculated as a difference between the total solvation enthalpy and the non-specific contribution. The latter was estimated via two different approaches in proton donor and proton accepting solvents. The effect of the cycle size on the strength of hydrogen bonding of the cyclic amides in solution is discussed.https://www.mdpi.com/1420-3049/26/5/1411solution enthalpiescyclic amidesproton acceptorsproton donorshydrogen bondingsolution calorimetry |
| spellingShingle | Ilnaz T. Rakipov Artem A. Petrov Aydar A. Akhmadiyarov Artashes A. Khachatrian Timur A. Mukhametzyanov Boris N. Solomonov Thermochemistry of Solution, Solvation, and Hydrogen Bonding of Cyclic Amides in Proton Acceptor and Donor Solvents. Amide Cycle Size Effect Molecules solution enthalpies cyclic amides proton acceptors proton donors hydrogen bonding solution calorimetry |
| title | Thermochemistry of Solution, Solvation, and Hydrogen Bonding of Cyclic Amides in Proton Acceptor and Donor Solvents. Amide Cycle Size Effect |
| title_full | Thermochemistry of Solution, Solvation, and Hydrogen Bonding of Cyclic Amides in Proton Acceptor and Donor Solvents. Amide Cycle Size Effect |
| title_fullStr | Thermochemistry of Solution, Solvation, and Hydrogen Bonding of Cyclic Amides in Proton Acceptor and Donor Solvents. Amide Cycle Size Effect |
| title_full_unstemmed | Thermochemistry of Solution, Solvation, and Hydrogen Bonding of Cyclic Amides in Proton Acceptor and Donor Solvents. Amide Cycle Size Effect |
| title_short | Thermochemistry of Solution, Solvation, and Hydrogen Bonding of Cyclic Amides in Proton Acceptor and Donor Solvents. Amide Cycle Size Effect |
| title_sort | thermochemistry of solution solvation and hydrogen bonding of cyclic amides in proton acceptor and donor solvents amide cycle size effect |
| topic | solution enthalpies cyclic amides proton acceptors proton donors hydrogen bonding solution calorimetry |
| url | https://www.mdpi.com/1420-3049/26/5/1411 |
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