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Identifying Different Halogen‐/Hydrogen‐Bonding Interaction Modes in Binary Systems that Contain an Acetate Ionic Liquid and Various Halobenzenes
Author(s) -
Xu Jing,
Zhou Yu,
Deng Geng,
Ashraf Hamad,
Yu ZhiWu
Publication year - 2018
Publication title -
chemphyschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.016
H-Index - 140
eISSN - 1439-7641
pISSN - 1439-4235
DOI - 10.1002/cphc.201701302
Subject(s) - chemistry , non covalent interactions , halogen , hydrogen bond , ionic liquid , ionic bonding , halogen bond , solvent , molecule , ion , crystallography , computational chemistry , organic chemistry , catalysis , alkyl
Elucidation of the nature of noncovalent interactions between ionic liquids (ILs) and halogenated molecules is of particular importance for both fundamental research and drug development. Herein, the noncovalent interactions between 1‐butyl‐3‐methyl‐imidazolium acetate and three halobenzenes C 6 F 5 X (X=I, Br, H) were investigated. The iodine derivative shows the strongest interaction with the IL, followed by C 6 F 5 Br and C 6 F 5 H. As indicated by the positive/negative peaks and “multi/two‐state” phenomena in the excess IR spectra, combined with DFT calculations, various interaction modes were differentiated. Three complexes, namely anion–C 6 F 5 I, anion–2 C 6 F 5 I, and ion‐pair–C 6 F 5 I in the IL–C 6 F 5 I system were identified, whereas only ion‐pair–C 6 F 5 Br/C 6 F 5 H complexes, together with self‐associates, were found in the other two systems. A possible reason for the behavior of the IL–C 6 F 5 I system could be that the iodine‐based halogen‐bonding interactions in the system are strong enough to break interactions between the IL cations and anions. This might make C 6 F 5 I a good co‐solvent to regulate the properties of acetate‐based ILs.