Analysis of the Frequency and Diversity of 1,3-Dialkylimidazolium Ionic Liquids Appearing in the Literature

Scalfani, Vincent F.; Al Alshaikh, Ali; Bara, Jason E.

doi:10.1021/acs.iecr.8b02573

Title: Analysis of the Frequency and Diversity of 1,3-Dialkylimidazolium Ionic Liquids Appearing in the Literature

Journal Article · Fri Aug 17 00:00:00 EDT 2018 · Industrial and Engineering Chemistry Research

DOI:https://doi.org/10.1021/acs.iecr.8b02573· OSTI ID:1830650

^[1]; Al Alshaikh, Ali ^[1];

^[1]

Univ. of Alabama, Tuscaloosa, AL (United States)

The hypothetical assertion that there are potentially millions of ionic liquids (ILs) can be validated using basic knowledge of IL precursors and simple calculations. While it is an interesting thought exercise to ponder the possibilities of ILs, it is important to investigate how many discrete ILs (i.e., unique cation and anion pairings) have actually been synthesized and reported in the literature. A complete analysis of all ILs is a daunting task, especially if the definition of what constitutes an IL is broad. Nonetheless, insight can be gained into the use of ILs over the past ~20 years from a focused analysis of systematically varied 1,3-dialkylimidazolium-based ILs (i.e., [R₁R₂im][X], where R₁ and R₂ are n-alkyl chains and X is either a halide or molecular anion). This family of ILs includes many of the most widely used and most thoroughly studied IL substances, including 1-butyl-3-methylimidazolium hexafluorophosphate ([C₄mim][PF₆]) and 1-ethyl-3-methylimidazolium bistriflimide ([C₂mim][Tf₂N]). Using data retrieved from SciFinder searches, we analyzed the variety and frequency of 1,3-dialkylimidazolium-based ILs appearing in the literature. Our analysis reveals that there is a relatively large number of simple 1,3-dialkylimidazolium cations which have not yet been synthesized. Our findings indicate that despite the broad possibilities of IL structures available, there are but a handful of ILs that are commonly used and studied. Within the 1248 [R₁R₂im][X] ILs studied, there were only 12 cations extensively used, which included [R₁R₂im]⁺ (R₁ = C₁ and R₂ = C₁–C₁₂). Of the 16 anions studied, only 5, including [BF₄]^–, [Cl]^–, [PF₆]^–, [Tf₂N]^–, and [Br]^–, were used significantly. Thus, it appears that although ILs can be used as designer solvents with task-specific properties, there is a small default subset of ILs, which are “go-to” or “one-size-fits-all.” Here, we rationalize the current state of the IL landscape in terms of the historical perceptions (and misconceptions) around ILs, familiarity, availability and cost of starting materials, commercial availability of ILs, and the motivations from which researchers choose to synthesize and characterize new ILs.

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Research Organization:: Univ. of Alabama, Tuscaloosa, AL (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES); National Science Foundation (NSF)

Grant/Contract Number:: SC0018181; 1605411

OSTI ID:: 1830650

Journal Information:: Industrial and Engineering Chemistry Research, Vol. 57, Issue 47; ISSN 0888-5885

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 20 works

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References (80)

Effect of hydrophobic side-chains on the solvation of imidazolium salts Headley, Allan D.; Kotti, S. R. S. Saibabu; Nam, Jaewook Journal of Physical Organic Chemistry, Vol. 18, Issue 10 https://doi.org/10.1002/poc.959	journal	January 2005
Efficient, halide free synthesis of new, low cost ionic liquids: 1,3-dialkylimidazolium salts containing methyl- and ethyl-sulfate anions Holbrey, John D.; Reichert, W. Matthew; Swatloski, Richard P. Green Chemistry, Vol. 4, Issue 5 https://doi.org/10.1039/b204469b	journal	September 2002
Ionic Liquid Crystals: Versatile Materials Goossens, Karel; Lava, Kathleen; Bielawski, Christopher W. Chemical Reviews, Vol. 116, Issue 8 https://doi.org/10.1021/cr400334b	journal	April 2016
Liquid-Crystalline Ionic Liquids as Ordered Reaction Media for the Diels-Alder Reaction Bruce, Duncan W.; Gao, Yanan; Canongia Lopes, José Nuno Chemistry - A European Journal, Vol. 22, Issue 45 https://doi.org/10.1002/chem.201602965	journal	September 2016
Evaluation of Thermophysical Properties of Functionalized Imidazolium Thiocyanate Based Ionic Liquids Gonfa, Girma; Bustam, Mohamad Azmi; Muhammad, Nawshad Industrial & Engineering Chemistry Research, Vol. 54, Issue 49 https://doi.org/10.1021/acs.iecr.5b03707	journal	December 2015
The Journal of Chemical Documentation and the Journal of Chemical Information and Computer Sciences : Publication and Citation Statistics Jishi, Rabab Al; Willett, Peter Journal of Chemical Information and Modeling, Vol. 50, Issue 11 https://doi.org/10.1021/ci100338j	journal	October 2010
Alkyltrioctylphosphonium chloride ionic liquids: synthesis and physicochemical properties Adamová, Gabriela; Gardas, Ramesh L.; Rebelo, Luís Paulo N. Dalton Transactions, Vol. 40, Issue 47 https://doi.org/10.1039/c1dt10332f	journal	January 2011
Nonaborane and Decaborane Cluster Anions Can Enhance the Ignition Delay in Hypergolic Ionic Liquids and Induce Hypergolicity in Molecular Solvents McCrary, Parker D.; Barber, Patrick S.; Kelley, Steven P. Inorganic Chemistry, Vol. 53, Issue 9 https://doi.org/10.1021/ic500622f	journal	April 2014
Ueber die Constitution des Lophins und verwandter Verbindungen Radziszewski, Br. Berichte der deutschen chemischen Gesellschaft, Vol. 15, Issue 2 https://doi.org/10.1002/cber.18820150207	journal	July 1882
Ionic Polyimides: Hybrid Polymer Architectures and Composites with Ionic Liquids for Advanced Gas Separation Membranes Mittenthal, Max S.; Flowers, Brian S.; Bara, Jason E. Industrial & Engineering Chemistry Research, Vol. 56, Issue 17 https://doi.org/10.1021/acs.iecr.7b00462	journal	April 2017
Application of Ionic Liquids Containing Tricyanomethanide [C(CN) ₃ ] ⁻ or Tetracyanoborate [B(CN) ₄ ] ⁻ Anions in Dye-Sensitized Solar Cells Marszalek, Magdalena; Fei, Zhaofu; Zhu, Dun-Ru Inorganic Chemistry, Vol. 50, Issue 22 https://doi.org/10.1021/ic201513m	journal	November 2011
Effect of Cation Symmetry on the Morphology and Physicochemical Properties of Imidazolium Ionic Liquids Zheng, Wei; Mohammed, Ali; Hines, Larry G. The Journal of Physical Chemistry B, Vol. 115, Issue 20 https://doi.org/10.1021/jp1115614	journal	May 2011
Guide to CO ₂ Separations in Imidazolium-Based Room-Temperature Ionic Liquids Bara, Jason E.; Carlisle, Trevor K.; Gabriel, Christopher J. Industrial & Engineering Chemistry Research, Vol. 48, Issue 6 https://doi.org/10.1021/ie8016237	journal	March 2009
A silver and water free metathesis reaction: a route to ionic liquids Srour, Hassan; Rouault, Hélène; Santini, Catherine C. Green Chemistry, Vol. 15, Issue 5 https://doi.org/10.1039/c3gc37034h	journal	January 2013
Odd-even effect on the formation of aqueous biphasic systems formed by 1-alkyl-3-methylimidazolium chloride ionic liquids and salts Belchior, Diana C. V.; Sintra, Tânia E.; Carvalho, Pedro J. The Journal of Chemical Physics, Vol. 148, Issue 19 https://doi.org/10.1063/1.5012020	journal	May 2018
Ether- and alcohol-functionalized task-specific ionic liquids: attractive properties and applications Tang, Shaokun; Baker, Gary A.; Zhao, Hua Chemical Society Reviews, Vol. 41, Issue 10 https://doi.org/10.1039/c2cs15362a	journal	January 2012
Vapor pressures of 1,3-dialkylimidazolium bis(trifluoromethylsulfonyl)imide ionic liquids with long alkyl chains Rocha, Marisa A. A.; Coutinho, João A. P.; Santos, Luís M. N. B. F. The Journal of Chemical Physics, Vol. 141, Issue 13 https://doi.org/10.1063/1.4896704	journal	October 2014
Densities, viscosities and derived thermophysical properties of water-saturated imidazolium-based ionic liquids Martins, Mónia A. R.; Neves, Catarina M. S. S.; Kurnia, Kiki A. Fluid Phase Equilibria, Vol. 407 https://doi.org/10.1016/j.fluid.2015.05.023	journal	January 2016
Ionic Liquid Crystals Binnemans, Koen Chemical Reviews, Vol. 105, Issue 11 https://doi.org/10.1021/cr0400919	journal	November 2005
Experimental Densities and Calculated Fractional Free Volumes of Ionic Liquids with Tri- and Tetra-substituted Imidazolium Cations Yue, Shuwen; Roveda, John D.; Mittenthal, Max S. Journal of Chemical & Engineering Data, Vol. 63, Issue 7 https://doi.org/10.1021/acs.jced.7b01033	journal	March 2018
Cation Alkyl Side Chain Length and Symmetry Effects on the Surface Tension of Ionic Liquids Almeida, Hugo F. D.; Freire, Mara G.; Fernandes, Ana M. Langmuir, Vol. 30, Issue 22 https://doi.org/10.1021/la501308q	journal	May 2014
Naturally Occurring and Synthetic Imidazoles: Their Chemistry and Their Biological Activities Luca, Lidia D. Current Medicinal Chemistry, Vol. 13, Issue 1 https://doi.org/10.2174/092986706775197971	journal	January 2006
Homogeneous Tritylation of Cellulose in 1-Butyl-3-methylimidazolium Chloride Erdmenger, Tina; Haensch, Claudia; Hoogenboom, Richard Macromolecular Bioscience, Vol. 7, Issue 4, p. 440-445 https://doi.org/10.1002/mabi.200600253	journal	April 2007
Benzyl-Functionalized Room Temperature Ionic Liquids for CO ₂ /N ₂ Separation Mahurin, Shannon M.; Dai, Thomas; Yeary, Joshua S. Industrial & Engineering Chemistry Research, Vol. 50, Issue 24 https://doi.org/10.1021/ie201428k	journal	November 2011
Alkylimidazolium Based Ionic Liquids: Impact of Cation Symmetry on Their Nanoscale Structural Organization Rocha, Marisa A. A.; Neves, Catarina M. S. S.; Freire, Mara G. The Journal of Physical Chemistry B, Vol. 117, Issue 37 https://doi.org/10.1021/jp406374a	journal	September 2013
From industrial black liquor to pure phenolic compounds: A combination of catalytic conversion with ionic liquids extraction Garron, Anthony; Arquilliere, Philippe P.; Maksoud, Walid Al Applied Catalysis A: General, Vol. 502 https://doi.org/10.1016/j.apcata.2015.06.012	journal	August 2015
InChI, the IUPAC International Chemical Identifier Heller, Stephen R.; McNaught, Alan; Pletnev, Igor Journal of Cheminformatics, Vol. 7, Issue 1 https://doi.org/10.1186/s13321-015-0068-4	journal	May 2015
Cation Symmetry effect on the Volatility of Ionic Liquids Rocha, Marisa A. A.; Coutinho, João A. P.; Santos, Luís M. N. B. F. The Journal of Physical Chemistry B, Vol. 116, Issue 35 https://doi.org/10.1021/jp306937f	journal	August 2012
Synthesis of 1,2-Dialkyl-, 1,4(5)-Dialkyl-, and 1,2,4(5)-Trialkylimidazoles via a One-Pot Method Hindman, Michelle S.; Stanton, Alexander D.; Irvin, A. Christopher Industrial & Engineering Chemistry Research, Vol. 52, Issue 34 https://doi.org/10.1021/ie401861b	journal	August 2013
Main-chain imidazolium polymer membranes for CO2 separations: An initial study of a new ionic liquid-inspired platform Carlisle, Trevor K.; Bara, Jason E.; Lafrate, Andrew L. Journal of Membrane Science, Vol. 359, Issue 1-2 https://doi.org/10.1016/j.memsci.2009.10.022	journal	September 2010
The Reaction of Carbonyldiimidazole with Alcohols to Form Carbamates and N- Alkylimidazoles Tang, Yuanqing; Dong, Yuxiang; Vennerstrom, Jonathan L. Synthesis, Vol. 2004, Issue 15 https://doi.org/10.1055/s-2004-831215	journal	January 2004
Imidazolium Based Ionic Liquids: Impact of the Cation Symmetry and Alkyl Chain Length on the Enthalpy of Vaporization: Imidazolium Based Ionic Liquids: Impact of the Cation Symmetry and Alkyl Chain Length on the Enthalpy of Vaporization Yermalayeu, Andrei V.; Zaitsau, Dzmitry H.; Loor, Manuel Zeitschrift für anorganische und allgemeine Chemie, Vol. 643, Issue 1 https://doi.org/10.1002/zaac.201600332	journal	November 2016
Dissolution of oligo(tetrafluoroethylene) and preparation of poly(tetrafluoroethylene)-based composites by using fluorinated ionic liquids Tsurumaki, Akiko; Ohno, Hiroyuki Chemical Communications, Vol. 54, Issue 4 https://doi.org/10.1039/C7CC08449H	journal	January 2018
Ueber einige neue Glyoxaline Radziszewski, Br. Berichte der deutschen chemischen Gesellschaft, Vol. 16, Issue 1 https://doi.org/10.1002/cber.188301601170	journal	January 1883
Evaluation of Cd(II) transport with imidazolium bromides bearing butyl and isobutyl groups as extractants from acidic iodide solutions by liquid–liquid solvent extraction Eyupoglu, Volkan; Polat, Emrah Fluid Phase Equilibria, Vol. 394 https://doi.org/10.1016/j.fluid.2015.03.003	journal	May 2015
Effect of cation symmetry on the organization of ionic liquids near a charged mica surface Payal, Rajdeep Singh; Balasubramanian, Sundaram Journal of Physics: Condensed Matter, Vol. 26, Issue 28 https://doi.org/10.1088/0953-8984/26/28/284101	journal	June 2014
Air and water stable 1-ethyl-3-methylimidazolium based ionic liquids Wilkes, John S.; Zaworotko, Michael J. Journal of the Chemical Society, Chemical Communications, Issue 13 https://doi.org/10.1039/c39920000965	journal	January 1992
Literature information in PubChem: associations between PubChem records and scientific articles Kim, Sunghwan; Thiessen, Paul A.; Cheng, Tiejun Journal of Cheminformatics, Vol. 8, Issue 1 https://doi.org/10.1186/s13321-016-0142-6	journal	June 2016
A physicochemical investigation of ionic liquid mixtures Clough, Matthew T.; Crick, Colin R.; Gräsvik, John Chemical Science, Vol. 6, Issue 2 https://doi.org/10.1039/C4SC02931C	journal	January 2015
Why Are Ionic Liquids Liquid? A Simple Explanation Based on Lattice and Solvation Energies Krossing, Ingo; Slattery, John M.; Daguenet, Corinne Journal of the American Chemical Society, Vol. 128, Issue 41 https://doi.org/10.1021/ja0619612	journal	October 2006
Physicochemical Properties and Structures of Room Temperature Ionic Liquids. 1. Variation of Anionic Species Tokuda, Hiroyuki; Hayamizu, Kikuko; Ishii, Kunikazu The Journal of Physical Chemistry B, Vol. 108, Issue 42 https://doi.org/10.1021/jp047480r	journal	October 2004
Enhanced CO ₂ Separation Selectivity in Oligo(ethylene glycol) Functionalized Room-Temperature Ionic Liquids Bara, Jason E.; Gabriel, Christopher J.; Lessmann, Sonja Industrial & Engineering Chemistry Research, Vol. 46, Issue 16 https://doi.org/10.1021/ie070437g	journal	August 2007
Ionic Liquids for Clean Technology Seddon, Kenneth R. Journal of Chemical Technology & Biotechnology, Vol. 68, Issue 4 https://doi.org/10.1002/(SICI)1097-4660(199704)68:4<351::AID-JCTB613>3.0.CO;2-4	journal	April 1997
Versatile and Scalable Method for Producing N -Functionalized Imidazoles Bara, Jason E. Industrial & Engineering Chemistry Research, Vol. 50, Issue 24 https://doi.org/10.1021/ie102535c	journal	December 2011
Open Babel: An open chemical toolbox O'Boyle, Noel M.; Banck, Michael; James, Craig A. Journal of Cheminformatics, Vol. 3, Issue 1 https://doi.org/10.1186/1758-2946-3-33	journal	October 2011
Hydrophobic, Highly Conductive Ambient-Temperature Molten Salts ^† Bonhôte, Pierre; Dias, Ana-Paula; Papageorgiou, Nicholas Inorganic Chemistry, Vol. 35, Issue 5 https://doi.org/10.1021/ic951325x	journal	January 1996
Structure-property relationships in ionic liquids: Chain length dependence of the vaporization enthalpies of imidazolium-based ionic liquids with fluorinated substituents Zaitsau, Dzmitry H.; Yermalayeu, Andrei V.; Verevkin, Sergey P. Thermochimica Acta, Vol. 622 https://doi.org/10.1016/j.tca.2015.04.021	journal	December 2015
A Highly Fluorescent Hydrophilic Ionic Liquid as a Potential Probe for the Sensing of Biomacromolecules Chen, Xu-Wei; Liu, Jia-Wei; Wang, Jian-Hua The Journal of Physical Chemistry B, Vol. 115, Issue 6 https://doi.org/10.1021/jp109121h	journal	January 2011
Beyond 1,3-difunctionalized imidazolium cations Bara, Jason E.; Shannon, Matthew S. Nanomaterials and Energy, Vol. 1, Issue 4 https://doi.org/10.1680/nme.12.00011	journal	July 2012
The Chemical Abstracts Service Chemical Registry System. VII. Tautomerism and Alternating Bonds Mockus, J.; Stobaugh, R. E. Journal of Chemical Information and Computer Sciences, Vol. 20, Issue 1 https://doi.org/10.1021/ci60021a007	journal	February 1980
Anion and Cation Effects on Imidazolium Salt Melting Points: A Descriptor Modelling Study López-Martin, Ignacio; Burello, Enrico; Davey, Paul N. ChemPhysChem, Vol. 8, Issue 5 https://doi.org/10.1002/cphc.200600637	journal	April 2007
A comparison of ether- and alkyl-derivatized imidazolium-based room-temperature ionic liquids: a molecular dynamics simulation study Smith, Grant D.; Borodin, Oleg; Li, Liyong Physical Chemistry Chemical Physics, Vol. 10, Issue 41 https://doi.org/10.1039/b808303g	journal	January 2008
A Simple and Practical Method for the Preparation and Purity Determination of Halide-Free Imidazolium Ionic Liquids Cassol, Claúdia C.; Ebeling, Günter; Ferrera, Bauer Advanced Synthesis & Catalysis, Vol. 348, Issue 1-2 https://doi.org/10.1002/adsc.200505295	journal	January 2006
The Stokes-Einstein equation and the diffusion of ferrocene in imidazolium-based ionic liquids studied by cyclic voltammetry: Effects of cation ion symmetry and alkyl chain length Thakurathi, Mahesh; Gurung, Eshan; Cetin, M. Mustafa Electrochimica Acta, Vol. 259 https://doi.org/10.1016/j.electacta.2017.10.149	journal	January 2018
Controlling Molecular Ordering in Aqueous Conducting Polymers Using Ionic Liquids Kee, Seyoung; Kim, Nara; Kim, Bong Seong Advanced Materials, Vol. 28, Issue 39 https://doi.org/10.1002/adma.201505473	journal	August 2016
Evidence of nanostructuration from the heat capacities of the 1,3-dialkylimidazolium bis(trifluoromethylsulfonyl)imide ionic liquid series Rocha, Marisa A. A.; Coutinho, João A. P.; Santos, Luís M. N. B. F. The Journal of Chemical Physics, Vol. 139, Issue 10 https://doi.org/10.1063/1.4820825	journal	September 2013
A comparison of fluoroalkyl-derivatized imidazolium:TFSI and alkyl-derivatized imidazolium:TFSI ionic liquids: a molecular dynamics simulation study Smith, Grant D.; Borodin, Oleg; Magda, Jules J. Physical Chemistry Chemical Physics, Vol. 12, Issue 26 https://doi.org/10.1039/c001387k	journal	January 2010
Symmetrical 1,3‐Dialkylimidazolium Based Ionic Liquid Crystals Rohini, Rondla; Lee, Ching‐Kuan; Lu, Jung‐Tang Journal of the Chinese Chemical Society, Vol. 60, Issue 7 https://doi.org/10.1002/jccs.201200598	journal	January 2013
The Chemical Abstracts Service Chemical Registry System. IV. Use of the Registry System to Support the Preparation of Index Nomenclature Stouw, Gerald G. Vander; Gustafson, Christine; Rule, John D. Journal of Chemical Information and Computer Sciences, Vol. 16, Issue 4 https://doi.org/10.1021/ci60008a006	journal	November 1976
PUG-SOAP and PUG-REST: web services for programmatic access to chemical information in PubChem Kim, Sunghwan; Thiessen, Paul A.; Bolton, Evan E. Nucleic Acids Research, Vol. 43, Issue W1 https://doi.org/10.1093/nar/gkv396	journal	April 2015
Inclusion Complexes of Ionic Liquids and Cyclodextrins: Are They Formed in the Gas Phase? Fernandes, Ana M.; Schröder, Bernd; Barata, Tânia Journal of the American Society for Mass Spectrometry, Vol. 25, Issue 5 https://doi.org/10.1007/s13361-013-0820-9	journal	March 2014
New room-temperature ionic liquids with C2-symmetrical imidazolium cations Dzyuba, Sergei V.; Bartsch, Richard A. Chemical Communications, Issue 16 https://doi.org/10.1039/b104512c	journal	January 2001
Linking the structures, free volumes, and properties of ionic liquid mixtures Brooks, Nicholas J.; Castiglione, Franca; Doherty, Cara M. Chemical Science, Vol. 8, Issue 9 https://doi.org/10.1039/C7SC01407D	journal	January 2017
SMILES, a chemical language and information system. 1. Introduction to methodology and encoding rules Weininger, David Journal of Chemical Information and Modeling, Vol. 28, Issue 1 https://doi.org/10.1021/ci00057a005	journal	February 1988
PubChem Substance and Compound databases Kim, Sunghwan; Thiessen, Paul A.; Bolton, Evan E. Nucleic Acids Research, Vol. 44, Issue D1 https://doi.org/10.1093/nar/gkv951	journal	September 2015
Effect of Cation Symmetry and Alkyl Chain Length on the Structure and Intermolecular Dynamics of 1,3-Dialkylimidazolium Bis(trifluoromethanesulfonyl)amide Ionic Liquids Xiao, Dong; Hines, Larry G.; Li, Shengfu The Journal of Physical Chemistry B, Vol. 113, Issue 18 https://doi.org/10.1021/jp8102595	journal	May 2009
Room temperature ionic liquids as novel media for ‘clean’ liquid–liquid extraction Huddleston, Jonathan G.; Willauer, Heather D.; Swatloski, Richard P. Chem. Commun., Issue 16 https://doi.org/10.1039/A803999B	journal	January 1998
Recent advances in the synthesis and structure–property relationships of ammonium ionenes Williams, Sharlene R.; Long, Timothy E. Progress in Polymer Science, Vol. 34, Issue 8 https://doi.org/10.1016/j.progpolymsci.2009.04.004	journal	August 2009
Physicochemical Properties and Structures of Room Temperature Ionic Liquids. 2. Variation of Alkyl Chain Length in Imidazolium Cation Tokuda, Hiroyuki; Hayamizu, Kikuko; Ishii, Kunikazu The Journal of Physical Chemistry B, Vol. 109, Issue 13 https://doi.org/10.1021/jp044626d	journal	April 2005
Ueber die Synthese der Oxalinbasen Radziszewski, Br. Berichte der deutschen chemischen Gesellschaft, Vol. 16, Issue 1 https://doi.org/10.1002/cber.188301601106	journal	January 1883
Role of Cation Symmetry in Intermolecular Structure and Dynamics of Room Temperature Ionic Liquids: Simulation Studies Raju, S. G.; Balasubramanian, S. The Journal of Physical Chemistry B, Vol. 114, Issue 19 https://doi.org/10.1021/jp9120673	journal	May 2010
CHEMISTRY: Ionic Liquids--Solvents of the Future? Rogers, R. D.; Seddon, Kenneth R. Science, Vol. 302, Issue 5646, p. 792-793 https://doi.org/10.1126/science.1090313	journal	October 2003
Syntheses of polyalkylated imidazoles Evjen, Sigvart; Fiksdahl, Anne Synthetic Communications, Vol. 47, Issue 15 https://doi.org/10.1080/00397911.2017.1330416	journal	June 2017
Improving the zT value of thermoelectrics by nanostructuring: tuning the nanoparticle morphology of Sb ₂ Te ₃ by using ionic liquids Schaumann, Julian; Loor, Manuel; Ünal, Derya Dalton Transactions, Vol. 46, Issue 3 https://doi.org/10.1039/C6DT04323B	journal	January 2017
Alkyl Chain Interaction at the Surface of Room Temperature Ionic Liquids: Systematic Variation of Alkyl Chain Length (R = C ₁ −C ₄ , C ₈ ) in both Cation and Anion of [RMIM][R − OSO ₃ ] by Sum Frequency Generation and Surface Tension Santos, Cherry S.; Baldelli, Steven The Journal of Physical Chemistry B, Vol. 113, Issue 4 https://doi.org/10.1021/jp807924g	journal	January 2009
Task-Specific Ionic Liquids H. Davis, Jr., James Chemistry Letters, Vol. 33, Issue 9 https://doi.org/10.1246/cl.2004.1072	journal	September 2004
Ionic Parachor and Its Application in Acetic Acid Ionic Liquid Homologue 1-Alkyl-3-methylimidazolium Acetate {[C _n mim][OAc]( n = 2,3,4,5,6)} Guan, Wei; Ma, Xiao-Xue; Li, Long The Journal of Physical Chemistry B, Vol. 115, Issue 44 https://doi.org/10.1021/jp207882t	journal	October 2011
Impact of the cation symmetry on the mutual solubilities between water and imidazolium-based ionic liquids Martins, Mónia A. R.; Neves, Catarina M. S. S.; Kurnia, Kiki A. Fluid Phase Equilibria, Vol. 375 https://doi.org/10.1016/j.fluid.2014.05.013	journal	August 2014
A task-specific ionic liquid [bmim]SCN for the conversion of alkyl halides to alkyl thiocyanates at room temperature Kamal, Ahmed; Chouhan, Gagan Tetrahedron Letters, Vol. 46, Issue 9 https://doi.org/10.1016/j.tetlet.2005.01.040	journal	February 2005
Gas separations in fluoroalkyl-functionalized room-temperature ionic liquids using supported liquid membranes Bara, Jason E.; Gabriel, Christopher J.; Carlisle, Trevor K. Chemical Engineering Journal, Vol. 147, Issue 1 https://doi.org/10.1016/j.cej.2008.11.021	journal	April 2009

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
ionic liquids
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imidazolium
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chemical information

Title: Analysis of the Frequency and Diversity of 1,3-Dialkylimidazolium Ionic Liquids Appearing in the Literature

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