Structural Motifs in Cold Ternary Ion Complexes of Hydroxyl-Functionalized Ionic Liquids: Isolating the Role of Cation-Cation Interactions

The Journal of Physical Chemistry Letters
Fabian S MengesRalf Ludwig

Abstract

We address the competition between intermolecular forces underlying the recent observation that ionic liquids (ILs) with a hydroxyl-functionalized cation can form domains with attractive interactions between the nominally repulsive positively charged constituents. Here we show that this behavior is present even in the isolated ternary (HEMIm+)2NTf2- complex (HEMIm+ = 1-(2-hydroxyethyl)-3-methylimidazolium) cooled to about 35 K in a photodissociation mass spectrometer. Of the three isomers isolated by double resonance techniques, one is identified to exhibit direct contact between the cations. This linkage involves a cooperative H-bond wherein the OH group on one cation binds to the OH group on the other, which then attaches to the basic N atom of the anion. Formation of this motif comes at the expense of the usually dominant interaction of the acidic C(2)H group on the Im ring with molecular anions, as evidenced by isomer-dependent shifts in the C(2)H vibrational fundamentals.

References

Jan 25, 2003·Science·William H RobertsonMark A Johnson
Nov 1, 2003·Science·Robin D Rogers, Kenneth R Seddon
Sep 1, 2005·Journal of the American Chemical Society·Yanting Wang, Gregory A Voth
Feb 17, 2006·Nature·Martyn J EarleJason A Widegren
Mar 29, 2007·The Journal of Physical Chemistry. B·Alessandro TrioloEmanuela Di Cola
Jun 26, 2007·The Journal of Physical Chemistry. a·João P LealKenneth R Seddon
Aug 23, 2007·Physical Chemistry Chemical Physics : PCCP·Seiji TsuzukiMasuhiro Mikami
Jun 21, 2008·Chemical Reviews·Philippe Hapiot, Corinne Lagrost
Mar 7, 2009·Angewandte Chemie·Haixiang GaoJean'ne M Shreeve
Mar 28, 2009·The Journal of Physical Chemistry. B·Ilya A Shkrob, James F Wishart
Mar 28, 2009·International Journal of Molecular Sciences·Demberelnyamba DorjnamjinYoung Key Shim
Jul 25, 2009·Nature Materials·Michel ArmandBruno Scrosati
Nov 26, 2010·Annual Review of Physical Chemistry·Edward W CastnerJames F Wishart
Sep 17, 2011·Angewandte Chemie·Yanqiang ZhangJean'ne M Shreeve
Oct 21, 2011·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Stephan EhrlichStefan Grimme
Nov 18, 2011·Physical Chemistry Chemical Physics : PCCP·Hermann WeingärtnerChristian Herrmann
Aug 27, 2013·Accounts of Chemical Research·Arron B WolkMark A Johnson
Nov 8, 2013·Chemical Reviews·Zhigang LeiBiaohua Chen
Dec 18, 2013·The Journal of Chemical Physics·Christopher J JohnsonMark A Johnson
Jan 15, 2015·Chemical Society Reviews·Patricia A HuntRichard P Matthews
Mar 10, 2015·Physical Chemistry Chemical Physics : PCCP·Kenny HankeElsa Sanchez-Garcia
Jun 2, 2015·Chemical Reviews·Robert HayesRob Atkin
May 3, 2012·The Journal of Physical Chemistry Letters·Christopher M LeavittMark A Johnson
Dec 17, 2015·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Ralf LudwigFrank A Weinhold
Apr 15, 2016·Chemical Reviews·Stefan GrimmeChristoph Bannwarth
Jun 15, 2016·Physical Chemistry Chemical Physics : PCCP·Ryan S BoothJaime A Stearns

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Citations

Mar 2, 2019·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Sumit Kumar PanjaAnnalisa Paolone
Oct 5, 2018·Scientific Reports·Thomas NiemannRalf Ludwig
Apr 5, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Enrico Bodo
Sep 15, 2018·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Sumit K PanjaJohannes Kiefer
Jan 24, 2019·Physical Chemistry Chemical Physics : PCCP·T NiemannR Ludwig
Oct 31, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Jule K Philipp, Ralf Ludwig
Feb 14, 2021·International Journal of Pharmaceutics·Anthony LaiChristopher J H Porter
Apr 21, 2021·Physical Chemistry Chemical Physics : PCCP·Frederik Philippi, Tom Welton
Apr 21, 2021·Physical Chemistry Chemical Physics : PCCP·Junwu ChenSuojiang Zhang
Jul 10, 2021·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Loai Al SheakhRalf Ludwig
Jan 1, 2020·The Journal of Physical Chemistry. a·Helen J ZengMark A Johnson
Nov 13, 2019·The Journal of Physical Chemistry Letters·Thomas NiemannRob Atkin
Oct 26, 2018·The Journal of Physical Chemistry. B·Bingyu NieWei Zhang
Oct 8, 2020·Chemical Reviews·Oscar Nordness, Joan F Brennecke
Apr 16, 2020·Chemical Reviews·Yong-Lei WangMichael D Fayer

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