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Dynamic Structure of Organic Compounds in Solution by Dynamic NMR Measurements and Quantum Molecular Dynamics Calculations: IV.1 Benzamideстатья
Информация о цитировании статьи получена из
Scopus
Статья опубликована в журнале из списка Web of Science и/или Scopus
Дата последнего поиска статьи во внешних источниках: 15 февраля 2024 г.
- Авторы: Stanishevskii V.V., Schestakova A.K., Chertkov V.A.
- Журнал: Russian Journal of Organic Chemistry
- Том: 59
- Номер: 8
- Год издания: 2023
- Издательство: Maik Nauka/Interperiodica Publishing
- Местоположение издательства: Russian Federation
- Первая страница: 1298
- Последняя страница: 1308
- Номер статьи: 1070-4280
- DOI: 10.1134/S107042802308002X
- Аннотация: To study the structure and dynamics of nitrogen-containing compounds, NMR parameters with directly involved nitrogen can provide valuable structure information. However, this information can only be obtained using 15N-enriched compounds due to low natural abundance of 15N and extremely short relaxation time of 14N. In the synthesis of benzamides from their 15N-ammonium salts, 15N-enriched benzamides are often used as intermediates. In the present work, we studied the dynamic structure of benzamide, which is controlled by two independent factors: hindered internal rotation of the NH2 group around the C(O)–N bond and of the amide group as a whole relative to the benzene ring. Deeper knowledge of the mechanism and parameters of these processes in amides is important for meaningful interpretation and prediction of the biological activity of aromatic amides in living systems and the strength and conformation of their supramolecular complexes with lanthanide and actinide ions. A double enriched [2H 5,15N]benzamide was synthesized to avoid undesirable superposition of the strong aro-matic multiplet on the amide signals in the 1H NMR spectra. The 1H NMR spectrum of this compound contained only strong signals of amide protons, which allowed accurate determination of the quantitative characteristics of the studied dynamic processes. The obtained experimental data are in good agreement with the results of quantum molecular dynamics simulation.
- Добавил в систему: Чертков Вячеслав Алексеевич