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Competing intramolecular vs. intermolecular hydrogen bonding in phosphoryl-containing secondary alkanols: A structural, spectroscopic and DFT studyстатья
Информация о цитировании статьи получена из
Web of Science,
Scopus
Статья опубликована в журнале из списка Web of Science и/или Scopus
Дата последнего поиска статьи во внешних источниках: 12 декабря 2018 г.
- Авторы: Pasechnik Margarita P., Matveeva Anna G., Lyssenko Konstantin A., Aysin Rinat R., Smol'yakov Alexander F., Zubavichus Yan V., Godovikov Ivan A., Goryunov Evgenii I.
- Журнал: Journal of Molecular Structure
- Том: 1175
- Год издания: 2019
- Издательство: Elsevier BV
- Местоположение издательства: Netherlands
- Первая страница: 874
- Последняя страница: 881
- DOI: 10.1016/j.molstruc.2018.08.009
- Аннотация: Intramolecular hydrogen bonding competes with intermolecular hydrogen bonding in alkanols containing Ph2P(O) group. A character of H-bonding in secondary alkanols Ph2P(O) (CR2)nCH2CH(OH)Me, where n ¼ 0 (1), n¼ 1, R¼H (2), and n ¼ 1, R ¼ Me (3) in crystal state and solutions has been studied by X-ray diffraction, FTIR, and diffusion ordered NMR spectroscopy (DOSY). Quantum chemical calculations and QTAIM analysis of isolated alkanol molecules and their dimers have been performed. In spite of slight difference in the structure of linker between P(O) and OH groups, the studied alcohols in crystal exhibit three types of H-bonds: dimer with intermolecular H-bond, polymeric chains with intermolecular Hbond, and monomer with intramolecular H-bond. Experimental data agree well with structural data of quantum chemical calculations at the M06-2x/6-311G (d,p) level of theory. Energy values (thermodynamic parameters) of DFT-optimized structures for gauche and anti isomers and dimers have been calculated. According to FTIR data in solutions (0.1e0.0001 M), alcohol 1 is the most associated, association of alcohol 2 is much less expressed, while alcohol 3 remains as H-bound monomer. Particle size assessed by DOSY relative to Ph3CH does not change on dilution for alcohols 2 and 3 but varies for alcohol 1.
- Добавил в систему: Горюнов Евгений Иосифович
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