Hydrogen-Bonding and the Dissolution Mechanism of Uracil in an Acetate Ionic Liquid: New Insights from NMR Spectroscopy and Quantum Chemical Calculations
authors Araujo, JMM; Pereiro, AB; Lopes, JNC; Rebelo, LPN; Marrucho, IM
nationality International
journal JOURNAL OF PHYSICAL CHEMISTRY B
keywords N-BODY CLUSTERS; CARBOXYLIC-ACIDS; BONDED COMPLEXES; MASS-SPECTROMETRY; INORGANIC SALTS; PHASE-BEHAVIOR; CARBON-DIOXIDE; CELLULOSE; WATER; DENSITY
abstract The dissolution of uracil-a pyrimidine nucleic acid base-in the ionic liquid 1-ethyl-3-methylimidazolium acetate ([C(2)mim][CH3COO]) has been investigated by methods of H-1 and C-13 NMR spectroscopy, H-1-H-1 NOESY NMR spectroscopy, and quantum chemical calculations. The uracil-[C(2)mim][CH3COO] interactions that define the dissolution mechanism comprise the hydrogen bonds between the oxygen atoms of the acetate anion and the hydrogen atoms of the N1-H and N3-H groups of uracil and also the hydrogen bonds between the most acidic aromatic hydrogen atom (H2) of the imidazolium cation and the oxygen atoms of the carbonyl groups of uracil. The bifunctional solvation nature of the ionic liquid can be inferred from the presence of interactions between both ions of the ionic liquid and the uracil molecule. The location of such interaction sites was revealed using NMR data (H-1 and C-13 chemical shifts both in the IL and in the uracil molecule), complemented by DFT calculations. NOESY experiments provided additional evidence concerning the cation uracil interactions.
publisher AMER CHEMICAL SOC
issn 1520-6106
year published 2013
volume 117
issue 15
beginning page 4109
ending page 4120
digital object identifier (doi) 10.1021/jp400749j
web of science category Chemistry, Physical
subject category Chemistry
unique article identifier WOS:000317950000018
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journal impact factor 3.146
5 year journal impact factor 3.101
category normalized journal impact factor percentile 60.204
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