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Determining the relative strengths of aromatic and aliphatic C―H⋅⋅⋅X hydrogen bonds in imidazolium ionic liquids through measurement of H/D isotope effects on 19 F nuclear shielding
Author(s) -
Bottini Gualberto,
Moyna Guillermo
Publication year - 2018
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.4615
Subject(s) - chemistry , ionic liquid , isotopologue , tetrafluoroborate , hexafluorophosphate , deuterium , kinetic isotope effect , alkyl , hydrogen bond , hydrogen , molecule , organic chemistry , catalysis , physics , quantum mechanics
The relative strengths of aromatic and aliphatic C―H⋅⋅⋅X hydrogen bonds in imidazolium ionic liquids were investigated through measurement of H/D isotope effects on the 19 F nuclear shielding of deuterated isotopologues of 1‐ n ‐butyl‐3‐methylimidazolium hexafluorophosphate and tetrafluoroborate ([C 4 mim]PF 6 and [C 4 mim]BF 4 ). Δ 19 F(H,D) values ranging from 9.7 to 49.7 ppb were observed for [C 4 mim]PF 6 isotopologues, while for the [C 4 mim]BF 4 series these went from 26.2 to 83.8 ppb. Our findings indicate that the interactions between the fluorinated anions and protons on the C‐1′ and C‐1″ position of the N ‐alkyl sidechains are comparable to, and in some cases stronger than, those involving protons on the aromatic ring, underscoring the role that these weak interionic forces have on the local ordering of imidazolium salts in the liquid state. Copyright © 2017 John Wiley & Sons, Ltd.