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Probing hydrogen bonding in CF₃-substituted Hydroxy-functionalized ionic liquids by FTIR spectroscopy and DFT calculations Научная публикация

Журнал Journal of Molecular Liquids
ISSN: 0167-7322 , E-ISSN: 1873-3166
Вых. Данные Год: 2026, Том: 453, Номер статьи : 129543, Страниц : DOI: 10.1016/j.molliq.2026.129543
Авторы Shalygin Anton S. 1 , Bryliakov Konstantin P. 1
Организации
1 Zelinsky Institute of Organic Chemistry RAS, Leninsky Pr. 47, Moscow 119991, Russia

Реферат: Hydroxy-functionalized ionic liquids are a promising class of task-specific ionic liquids in which one or more hydroxyl groups are incorporated into the cation, resulting in novel physicochemical properties. One of the interesting phenomena stemming therefrom is the formation of “anti-electrostatic” hydrogen bonds between the hydroxyl groups of adjacent cations. Herein, a series of new ionic liquids containing cations with 1,1,1-trifluoro2-hydroxypropyl group have been synthesized. These include the 1-(1,1,1-trifluoro-2-hydroxypropyl)-3-methylimidazolium ([HOCH(CF₃)CH₂MIM]+) and 1-(1,1,1-trifluoro-2-hydroxypropyl)-2,3-dimethylimidazolium ([HOCH(CF₃)CH₂DMIM]+) cations in combination with [Br]− , [BF₄] − , and [NTf₂] − anions. Formation of hydrogen bonds between the OH groups and the influence of CF3 substituents on this interaction were studied by means of ATR-FTIR spectroscopy and single-crystal X-ray diffraction. The OH group of the HOCH(CF₃)CH₂ moiety exhibits a stronger interaction with the anions than in the HOCH₂CH₂ counterpart. The acidic properties of ILs containing the HOCH(CF₃)CH₂ group are similar to those of 2,2,2-trifluoroethanol. The O–H stretching vibration bands affected by hydrogen bonding with the OH of the adjacent cations were identified. DFT calculations combined with non-covalent bonding analysis using the independent gradient model based on Hirshfeld partition (IGMH) witness that hydrogen bonds between the OH groups, as well as between other hydrogen atoms in the HOCH(CF₃)CH₂ group of the cations play the key role in the cation-anion as well as cation-cation interactions.
Библиографическая ссылка: Shalygin A.S. , Bryliakov K.P.
Probing hydrogen bonding in CF₃-substituted Hydroxy-functionalized ionic liquids by FTIR spectroscopy and DFT calculations
Journal of Molecular Liquids. 2026. V.453. 129543 . DOI: 10.1016/j.molliq.2026.129543 Scopus OpenAlex
Даты:
Поступила в редакцию: 11 февр. 2026 г.
Принята к публикации: 1 апр. 2026 г.
Опубликована online: 3 апр. 2026 г.
Идентификаторы БД:
≡ Scopus: 2-s2.0-105034731486
≡ OpenAlex: W7148786453
Альметрики: