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NMR-monitoring of H/D exchange reaction of ketones in solutions of imidazolium ionic liquids Full article

Journal Journal of Molecular Liquids
ISSN: 0167-7322 , E-ISSN: 1873-3166
Output data Year: 2022, Volume: 362, Article number : 119746, Pages count : DOI: 10.1016/j.molliq.2022.119746
Authors Shahkhatuni Astghik A. 1 , Shahkhatuni Aleksan G. 1 , Ananikov Valentine P. 2 , Harutyunyan Arpine S. 1
Affiliations
1 Scientific Technological Center of Organic and Pharmaceutical Chemistry of NAS RA, Yerevan, Armenia
2 Zelinsky Institute of Organic Chemistry of RAS, Moscow, Russian Federation

Abstract: NMR spectroscopy was used to study hydrogen–deuterium exchange in CH3, CH2 and CH moieties of ketones dissolved in mixtures of solvents containing exchangeable deuteriums and imidazolium ionic liquids (IL) acting as catalysts. Factors affecting the efficiency of the exchange, as well as the role of the deuterated solvent, temperature and concentration, were investigated. Depending on the sample composition and temperature, the degree of deuteration can reach different values at equilibrium state, and the exchange rate can vary from several minutes to several months. ILs with OAc anions and with ethyl chain cations exhibit significant catalytic properties and high degrees of deuteration (up to 98%), which can be achieved by consecutive deuteration cycles. A convenient practical protocol for monitoring the exchange process by NMR spectroscopy and calculating the degree of deuteration was developed and can be used for various molecular systems.
Cite: Shahkhatuni A.A. , Shahkhatuni A.G. , Ananikov V.P. , Harutyunyan A.S.
NMR-monitoring of H/D exchange reaction of ketones in solutions of imidazolium ionic liquids
Journal of Molecular Liquids. 2022. V.362. 119746 . DOI: 10.1016/j.molliq.2022.119746 WOS Scopus OpenAlex
Identifiers:
Web of science: WOS:000827849900001
Scopus: 2-s2.0-85133408670
OpenAlex: W4283818103
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OpenAlex 6
Web of science 6
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