Summary.
A review of the recent developments in the study and understanding of room temperature ionic liquids are given. An intimate picture of how and why these liquids are not crystals at ambient conditions is attempted, based on evidence from crystallographical results combined with vibrational spectroscopy and ab-initio molecular orbital calculations. A discussion is given, based mainly on some recent FT-Raman spectroscopic results on the model ionic liquid system of 1-butyl-3-methylimidazolium ([C4 mim][X]) salts. The rotational isomerism of the [C4 mim]+ cation is described: the presence of anti and gauche conformers that has been elucidated in remarkable papers by Hamaguchi et al. Such presence of a conformational equilibrium seems to be a general feature of the room temperature liquids. Then the “localized structure features” that apparently exist in ionic liquids are described. It is hoped that the structural resolving power of Raman spectroscopy will be appreciated by the reader. It is of remarkable use on crystals of known different conformations and on the corresponding liquids, especially in combination with modern quantum mechanics calculations. It is hoped that these interdisciplinary methods will be applied to many more systems in the future. A few examples will be discussed.
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References
MJ Earle JMSS Esperanca MA Gilea JNC Lopes LPN Rebolo JW Magee KR Seddon JA Widegren (2006) Nature 439 831 Occurrence Handle1:CAS:528:DC%2BD28XhsVSkurk%3D Occurrence Handle10.1038/nature04451
JS Wilkes JA Levisky RA Wilson CL Hussey (1982) Inorg Chem 21 1263 Occurrence Handle1:CAS:528:DyaL38XhtVCitrw%3D Occurrence Handle10.1021/ic00133a078
Hussey CL (1983) In: Mamantov G, Mamantov CB (eds) Adv Molten Salt Chem. Elsevier, Vol. 5, p 185
P Bonhôte AP Dias M Armand N Papageorgiou K Kalyanasundaram M Grätzel (1996) Inorg Chem 35 1168 Occurrence Handle10.1021/ic951325x
KR Seddon (1997) J Chem Tech Biotechnol 68 351 Occurrence Handle1:CAS:528:DyaK2sXisFWksr8%3D Occurrence Handle10.1002/(SICI)1097-4660(199704)68:4<351::AID-JCTB613>3.0.CO;2-4
CM Gordon JD Holbrey AR Kennedy KR Seddon (1998) J Mater Chem 8 2627 Occurrence Handle1:CAS:528:DyaK1cXnvVSmsrs%3D Occurrence Handle10.1039/a806169f
JD Holbrey KR Seddon (1999) Ionic Liquids. Clean Products Processes 1 223
P Wasserscheid W Keim (2000) Angew Chem (Int Edit Engl) 39 3773
KR Seddon A Stark MJ Torres (2000) Pure Appl Chem 72 2275 Occurrence Handle1:CAS:528:DC%2BD3MXisVCgtb4%3D Occurrence Handle10.1351/pac200072122275
JG Huddleston AE Visser WM Reichert HD Willauer GA Broker RD Rogers (2001) Green Chem 3 156 Occurrence Handle1:CAS:528:DC%2BD3MXmtVWhsr8%3D Occurrence Handle10.1039/b103275p
Wasserscheid P, Welton T (eds) (2002–2003) Ionic Liquids in Synthesis. Wiley-VCH
JS Wilkes (2004) J Mol Catal A Chem 214 11 Occurrence Handle1:CAS:528:DC%2BD2cXjtVensLs%3D Occurrence Handle10.1016/j.molcata.2003.11.029
JS Wilkes (2002) Green Chem 4 73 Occurrence Handle1:CAS:528:DC%2BD2cXksVCgsb4%3D Occurrence Handle10.1039/b110838g
RJ Gale B Gilbert RA Osteryoung (1978) Inorg Chem 17 2728 Occurrence Handle1:CAS:528:DyaE1cXlsFCqsrk%3D Occurrence Handle10.1021/ic50188a008
N Koura (2005) Yoyuen oyobi Koon Kagaku 48 IssueID1 11 Occurrence Handle1:CAS:528:DC%2BD2MXksFOgt78%3D
P Tian X Song Y Li J Duan Z Liang H Zhang (2006) Huaxue Xuebao 64 IssueID23 2305 Occurrence Handle1:CAS:528:DC%2BD2sXjsVE%3D
M Castriota T Caruso RG Agostino E Cazzanelli WA Henderson S Passerini (2005) J Phys Chem A 109 92 Occurrence Handle1:CAS:528:DC%2BD2cXhtVOrur%2FK Occurrence Handle10.1021/jp046030w
I Nicotera C Oliviero WA Henderson GB Appetecchi S Passerini (2005) J Phys Chem B 109 22814 Occurrence Handle1:CAS:528:DC%2BD2MXhtF2ht7%2FN Occurrence Handle10.1021/jp053799f
PC Howlett N Brack AF Hollenkamp M Forsyth DR MacFarlane (2006) J Electrochem Soc 153 A595 Occurrence Handle1:CAS:528:DC%2BD28XhtlOjtLk%3D Occurrence Handle10.1149/1.2164726
T Fujimori K Fujii R Kanzaki K Chiba H Yamamoto Y Umebayashi S Ishiguro (2007) J Mol Liquids 131–132 216 Occurrence Handle10.1016/j.molliq.2006.08.054 Occurrence Handle1:CAS:528:DC%2BD2sXit1Omtg%3D%3D
X Liu S Zhang G Zhou G Wu X Yuan X Yao (2006) J Phys Chem B 110 12062 Occurrence Handle1:CAS:528:DC%2BD28XltV2kt74%3D Occurrence Handle10.1021/jp060834p
a) Huang J, Riisager A, Wasserscheid P, Fehrmann R (2006) Chem Commun 2006: 4027; b) Huang J, Riisager A, Berg RW, Fehrmann R (2007) Tuning Ionic Liquids for High Gas Solubility Reversible Gas Sorption. J Mol Catal A (Chemical), Doi: 10.1016/j.molcala.2007.07.036, in press
K Malek M Skubel G Schroeder OP Shvaika LM Proniewicz (2006) Vibr Spectrosc 42 317 Occurrence Handle1:CAS:528:DC%2BD28Xht1Wqt77I Occurrence Handle10.1016/j.vibspec.2006.05.017
K Malek A Puc G Schroeder VI Rybachenko LM Proniewicz (2006) Chem Phys 327 439 Occurrence Handle1:CAS:528:DC%2BD28XptVGksLo%3D Occurrence Handle10.1016/j.chemphys.2006.05.021
JG Huddleston HD Willauer RP Swatloski AE Visser RD Rogers (1998) Chem Commun 16 1765 Occurrence Handle10.1039/a803999b
DW Rooney KR Seddon (2001) NoChapterTitle G Wypych (Eds) Handbook of Solvents ChemTech Publishing Toronto 1459
Seddon KR (1999) In: Boghosian S, Dracopoulos V, Kontoyannis CG, Voyiatzis GA (eds) Proc. Int. George Papatheodorou Symposium. Patras Institute of Chemical Engineering High Temperature Chemical Processes, Greece, p 131
Seddon KR, Stark A, Torres MJ (2002) In: Abraham MA, Moens L (eds) Clean Solvents Alternative Media for Chemical Reactions Processing. ACS Symp Ser No. 819, Washington, DC, p 34
A Aggarwal NL Lancaster AR Sethi T Welton (2002) Green Chem 4 517 Occurrence Handle1:CAS:528:DC%2BD38XnsFCjsrw%3D Occurrence Handle10.1039/b206472c
L Crowhurst NL Lancaster JMP Arlandis T Welton (2004) J Am Chem Soc 126 11549 Occurrence Handle1:CAS:528:DC%2BD2cXntVCktrk%3D Occurrence Handle10.1021/ja046757y
MJ Earle SP Katdare KR Seddon (2004) Org Lett 6 707 Occurrence Handle1:CAS:528:DC%2BD2cXosl2qsQ%3D%3D Occurrence Handle10.1021/ol036310e
T Welton (1999) Chem Rev 99 2071 Occurrence Handle1:CAS:528:DyaK1MXkt1artrw%3D Occurrence Handle10.1021/cr980032t
CM Gordon (2001) Appl Catal A General 222 101 Occurrence Handle1:CAS:528:DC%2BD38XjvFSm Occurrence Handle10.1016/S0926-860X(01)00834-1
CF Ye WM Liu YX Chen LG Yu (2001) Chem Comm 2001 2244 Occurrence Handle10.1039/b106935g Occurrence Handle1:CAS:528:DC%2BD3MXnslChu7w%3D
MJ Earle (2002) NoChapterTitle RD Rogers KR Seddon (Eds) Ionic Liquids: Industrial Applications for Green Chemistry NumberInSeries818 American Chemical Society Washington, DC 90
Davis JH Jr (2003) Ionic Liquids in Synthesis. Wiley-VCH, p 33
JH Davis SuffixJr (2004) Chem Lett 33 1072 Occurrence Handle1:CAS:528:DC%2BD2cXnslSrtrY%3D Occurrence Handle10.1246/cl.2004.1072
MJ Park JK Lee BS Lee YW Lee IS Choi S Lee (2006) Chem Mater 18 1546 Occurrence Handle1:CAS:528:DC%2BD28Xht1ajsL4%3D Occurrence Handle10.1021/cm0511421
D Wei C Kvarnstroem T Lindfors A Ivaska (2007) Electrochem Commun 9 206 Occurrence Handle1:CAS:528:DC%2BD2sXhsFOhu70%3D Occurrence Handle10.1016/j.elecom.2006.09.008
S Tait RA Osteryoung (1984) Inorg Chem 23 4352 Occurrence Handle1:CAS:528:DyaL2MXhsVakug%3D%3D Occurrence Handle10.1021/ic00193a049
J Dupont RF de Souza PAZ Suarez (2002) Chem Rev (Washington, DC) 102 3667 Occurrence Handle1:CAS:528:DC%2BD38Xmt1Oqur4%3D
CJ Dymek SuffixJr JJP Stewart (1989) Inorg Chem 28 1472 Occurrence Handle1:CAS:528:DyaL1MXhs1amu7w%3D Occurrence Handle10.1021/ic00307a011
CG Hanke SL Price RM Lynden-Bell (2001) Molec Phys 99 801 Occurrence Handle1:CAS:528:DC%2BD3MXjsl2gur4%3D Occurrence Handle10.1080/00268970010018981
Z Meng A Dölle WR Carper (2002) J Molec Struct (THEOCHEM) 585 119 Occurrence Handle1:CAS:528:DC%2BD38XktVWgt7w%3D Occurrence Handle10.1016/S0166-1280(02)00056-8
Carper WR, Meng Z, Wasserscheid P, Dölle A (2002) In: Trulove PC, DeLong HC, Mantz RA (eds) Int. Symp. Molten Salts. Electrochem. Soc. Proc. Vol. 2002–19 (Molten Salts XIII), p 973
Carper WR, Meng Z, Dölle A (2003) In: Welton T, Wasserscheid P (eds) Ionic Liquids in Synthesis. Wiley, p 152
JK Shah JF Brennecke EJ Maginn (2004) Green Chem 4 112 Occurrence Handle10.1039/b110725a Occurrence Handle1:CAS:528:DC%2BD38XivVakt70%3D
CJ Dymek DA Grossie AV Fratini WW Adams (1989) J Molec Struct 213 25 Occurrence Handle1:CAS:528:DyaK3cXovVOnsA%3D%3D Occurrence Handle10.1016/0022-2860(89)85103-8
JS Wilkes MJ Zaworotko (1993) Supramolec Chem 1 191 Occurrence Handle1:CAS:528:DyaK2cXksVOisbs%3D Occurrence Handle10.1080/10610279308035160
J Fuller RT Carlin HC DeLong D Haworth (1994) Chem Commun 1994 299
AJ Carmichael C Hardacre JD Holbrey M Nieuwenhuyzen KR Seddon (2001) Molec Phys 99 795 Occurrence Handle1:CAS:528:DC%2BD3MXjsl2gtbc%3D Occurrence Handle10.1080/00268970010012301
AE Bradley C Hardacre JD Holbrey S Johnston SEJ McMath M Nieuwenhuyzen (2002) Chem Mater 14 629 Occurrence Handle1:CAS:528:DC%2BD38XjslSltA%3D%3D Occurrence Handle10.1021/cm010542v
AA Fannin DA Floreani LA King LS Landers BJ Piersma DJ Stech RL Vaughn JS Wilkes JL Williams (1984) J Phys Chem 88 2614 Occurrence Handle1:CAS:528:DyaL2cXitFKltLY%3D Occurrence Handle10.1021/j150656a038
CK Larive M Lin BJ Piersma WR Carper (1995) J Phys Chem 99 12409 Occurrence Handle1:CAS:528:DyaK2MXntFCgtrc%3D Occurrence Handle10.1021/j100033a008
WR Carper GJ Mains BJ Piersma SL Mansfield CK Larive (1996) J Phys Chem 100 4724 Occurrence Handle1:CAS:528:DyaK28Xhtleitrg%3D Occurrence Handle10.1021/jp953199o
J Fuller RT Carlin RA Osteryoung (1997) J Electrochem Soc 144 3881 Occurrence Handle1:CAS:528:DyaK2sXnsV2nsrc%3D Occurrence Handle10.1149/1.1838106
CK Larive M Lin BS Kinnear BJ Piersma CE Keller WR Carper (1998) J Phys Chem 102B 1717
AB McEwen EL Ngo K LeCompte JL Goldman (1999) J Electrochem Soc 146 1687 Occurrence Handle1:CAS:528:DyaK1MXjsVartbw%3D Occurrence Handle10.1149/1.1391827
A Dölle WR Carper (2003) NoChapterTitle T Welton P Wasserscheid (Eds) Ionic Liquids for Synthesis Wiley New York 168
A Elaiwi PB Hitchcock KR Seddon N Srinivasan YM Tan T Welton JA Zora (1995) J Chem Soc Dalton Trans 1995 3467 Occurrence Handle10.1039/dt9950003467
AK Abdul-Sada AM Greenway PB Hitchcock TJ Mohammed KR Seddon JA Zora (1986) J Chem Soc Chem Commun 1986 1753 Occurrence Handle10.1039/c39860001753
AK Abdul-Sada S Al-Juaid AM Greenway PB Hitchcock MJ Howells KR Seddon T Welton (1990) Struct Chem 1 391 Occurrence Handle1:CAS:528:DyaK3MXitlWktg%3D%3D Occurrence Handle10.1007/BF01374488
PB Hitchcock KR Seddon T Welton (1993) J Chem Soc Dalton Trans 1993 2639 Occurrence Handle10.1039/dt9930002639
AG Avent PA Chaloner MP Day KR Seddon T Welton (1994) J Chem Soc Dalton Trans 1994 3405 Occurrence Handle10.1039/dt9940003405
AK Abdul-Sada AE Elaiwi AM Greenway KR Seddon (1997) Eur Mass Spectrom 3 245 Occurrence Handle1:CAS:528:DyaK2sXlsFWms7s%3D
Huang JF, Chen PY, Sun IW, Wang SP (2001) Inorg Chim Acta 320: 7, same paper also published in Spectrosc Lett 34(5): 591
SA Katsyuba PJ Dyson EE Vandyukova AV Chernova A Vidis (2004) Helv Chim Acta 87 2556 Occurrence Handle1:CAS:528:DC%2BD2cXpvVyhurg%3D Occurrence Handle10.1002/hlca.200490228
L Cammarata SG Kazarian PA Salter T Welton (2001) Phys Chem Chem Phys 3 5192 Occurrence Handle1:CAS:528:DC%2BD3MXosFOgtr0%3D Occurrence Handle10.1039/b106900d
Welton T, Kazarian S, Crowhurst L, Perez-Arlandis JM, Salter P (2002) Abstr. 224th Am. Chem. Soc. National Meeting, Boston MA, August 18–22, 2002 224: 139
VJ Storhaug WR Carper (2003) Trends in Phys Chem 9 173 Occurrence Handle1:CAS:528:DC%2BD2MXhslyitb8%3D
F Endres S Zein El Abedin (2006) Phys Chem Chem Phys 8 2101 Occurrence Handle1:CAS:528:DC%2BD28XlsVOmsL0%3D Occurrence Handle10.1039/b600519p
K Matsumoto R Hagiwara R Yoshida Y Ito Z Mazej P Benkic B Zemva O Tamada H Yoshino S Matsubara (2004) Dalton Trans 2004 144 Occurrence Handle10.1039/b310162b Occurrence Handle1:CAS:528:DC%2BD2cXnslKisg%3D%3D
K Matsumoto R Hagiwara (2005) J Fluorine Chem 126 1095 Occurrence Handle1:CAS:528:DC%2BD2MXmtlOhtrs%3D Occurrence Handle10.1016/j.jfluchem.2005.03.018
CD Tran SHD Lacerda D Oliveira (2003) Appl Spectrosc 57 152 Occurrence Handle1:CAS:528:DC%2BD3sXivFaju7k%3D Occurrence Handle10.1366/000370203321535051
B Gilbert Y Chauvin I Guibard (1991) Vibr Spectrosc 1 299 Occurrence Handle1:CAS:528:DyaK3MXlsVGhtrs%3D Occurrence Handle10.1016/0924-2031(91)85007-A
Gilbert B, Pauly JP, Chauvin Y, Di Marco-Van Tiggelen F (1994) Molten Salts. In: Hussey CL, et al (eds) Proc. 9th Int. Symposium Electrochem. Soc., Pennington NJ, Vol. 94(13), p 218
Y Chauvin F Di Marco-Van Tiggelen H Olivier (1993) J Chem Soc Dalton Trans 1993 1009 Occurrence Handle10.1039/dt9930001009
P He H Liu Z Li Y Liu X Xu J Li (2004) Langmuir 20 10260 Occurrence Handle1:CAS:528:DC%2BD2cXosVOkur0%3D Occurrence Handle10.1021/la048480l
T Schafer RE Di Paolo R Franco JG Crespo (2005) Chem Commun 20 2594 Occurrence Handle10.1039/b501507c Occurrence Handle1:CAS:528:DC%2BD2MXkt1SgsLs%3D
N Nanbu Y Sasaki F Kitamura (2003) Electrochem Commun 5 383 Occurrence Handle1:CAS:528:DC%2BD3sXjs1SisLs%3D Occurrence Handle10.1016/S1388-2481(03)00073-0
VO Santos SuffixJr MB Alves MS Carvalho PAZ Suarez JC Rubim (2006) J Phys Chem B 110 20379 Occurrence Handle1:CAS:528:DC%2BD28XpsVykur0%3D Occurrence Handle10.1021/jp0643348
C Romero S Baldelli (2006) J Phys Chem B 110 6213 Occurrence Handle1:CAS:528:DC%2BD28XitVeku7o%3D Occurrence Handle10.1021/jp0565150
A Riisager R Fehrmann RW Berg R van Hal P Wasserscheid (2005) Phys Chem Chem Phys 7 3052 Occurrence Handle1:CAS:528:DC%2BD2MXmvVOhsb0%3D Occurrence Handle10.1039/b505588a
CV Raman KS Krishnan (1928) Nature 121 501 Occurrence Handle1:CAS:528:DyaB1cXhs1Ciug%3D%3D
Placzek G (1934) Rayleigh-Streuung und Raman Effekt, in Handbuch der Radiologie, Vol. VI. In: Marx E (ed) Akademische Verlagsgesellschaft, Leipzig, Germany, or English translation
G Herzberg (1945) Molecular Spectra Molecular Structure, Vol. II. Infrared Raman Spectra of Polyatomic Molecules van Nostrand New York
EB Wilson SuffixJr JC Decius PC Cross (1955) Molecular Vibrations SeriesTitleThe Theory of Infrared Raman Vibrational Spectra McGraw-Hill Book Co. New York
Long DA (2002) The Raman Effect: A Unified Treatment of the Theory of Raman Scattering by Molecules. Wiley, ISBN 0471490288
M Diem (1993) Introduction to Modern Vibrational Spectroscopy Wiley New York, USA
JJ Laserna (Eds) (1996) Modern Techniques in Raman Spectroscopy Wiley Chichester UK
J Coates (1998) Appl Spectrosc Rev 33 267 Occurrence Handle1:CAS:528:DyaK1MXltl2gsQ%3D%3D Occurrence Handle10.1080/05704929808002060
RL McCreery (2001) Raman Spectroscopy for Chemical Analysis Wiley Chichester
Smith E, Dent G (2005) Modern Raman Spectroscopy – A Practical Approach, Wiley
B Schrader (1989) Raman/Infrared Atlas of Organic Compounds EditionNumber2 V.C.H. and Wiley New York
D Lin-Vien NB Colthup WG Fateley JG Grasselli (1991) Handbook of Infrared and Raman Characteristic Frequencies of Organic Molecules Academic Press New York
RA Nyquist RO Kagel CL Putzig MA Leugers (1996) Handbook of Infrared and Raman Spectra of Inorganic Compounds and Organic Salts NumberInSeries4 Academic Press New York, London
K Nakamoto (1997) Infrared and Raman Spectra of Inorganic and Coordination Compounds, 5th edn. Part A: Theory and Applications in Inorganic Chemistry, and Part B, Applications in Coordination, Organometallic and Bioinorganic Chemistry Wiley New York
BC Smith (1998) Infrared Spectral Interpretation – A Systematic Approach CRC Press Inc. Boca Raton
G Socrates (2001) Infrared and Raman Characteristic Group Frequencies, Tables and Charts EditionNumber3 Wiley Chichester, UK
DM Bishop (1973) Group Theory and Chemistry Clarendon Press Oxford
RL Carter (1998) Molecular Symmetry and Group Theory Wiley New York
DB Chase JF Rabolt (1994) Fourier Transform Raman Spectroscopy Academic Press New York
RW Berg M Deetlefs KR Seddon I Shim JM Thompson (2005) J Phys Chem B 109 19018 Occurrence Handle1:CAS:528:DC%2BD2MXhtVShsLzO Occurrence Handle10.1021/jp050691r
Atkins P, de Paula J (2006) Atkins’ Physical Chemistry, 8th edn. Oxford University Press
MA Ratner GC Schatz (2001) Introduction to Quantum Mechanics in Chemistry Prentice-Hall Inc. NJ
Atkins PW, Friedman RS (2004) Molecular Quantum Mechanics, 4th edn. Oxford University Press
Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA (2004) Gaussian03, Revision C.02, Gaussian, Inc., Wallingford CT
H Hamaguchi R Ozawa (2005) Adv Chem Phys 131 85 Occurrence Handle1:CAS:528:DC%2BD2MXmtFKnu78%3D Occurrence Handle10.1002/0471739464.ch3
JD Holbrey KR Seddon (1999) J Chem Soc Dalton Trans 1999 2133 Occurrence Handle10.1039/a902818h
C Hardacre JD Holbrey PB McCormac SEJ McMath M Nieuwenhuyzen KR Seddon (2001) J Mater Chem 11 346 Occurrence Handle1:CAS:528:DC%2BD3MXntF2kug%3D%3D Occurrence Handle10.1039/b008091h
C Hardacre JD Holbrey SEJ McMath DT Bowron AK Soper (2003) J Chem Phys 118 273 Occurrence Handle1:CAS:528:DC%2BD38XpsFKqtLs%3D Occurrence Handle10.1063/1.1523917
C Hardacre SEJ McMath M Nieuwenhuyzen DT Bowron AK Soper (2003) J Phys-Condens Matter 15 S159 Occurrence Handle1:CAS:528:DC%2BD3sXhtFGqtr4%3D Occurrence Handle10.1088/0953-8984/15/1/320
A Triolo O Russina V Arrighi F Juranyi S Janssen CM Gordon (2003) J Chem Phys 119 8549 Occurrence Handle1:CAS:528:DC%2BD3sXotVKksrs%3D Occurrence Handle10.1063/1.1613637
JD Roche CM Gordon CT Imrie MD Ingram AR Kennedy F Lo Celso A Triolo (2003) Chem Mater 15 3089 Occurrence Handle10.1021/cm021378u Occurrence Handle1:CAS:528:DC%2BD3sXltVWlurw%3D
MA Firestone JA Dzielawa P Zapol LA Curtiss S Seifert ML Dietz (2002) Langmuir 18 7258 Occurrence Handle1:CAS:528:DC%2BD38Xms1Cnt7g%3D Occurrence Handle10.1021/la0259499
S Saha S Hayashi A Kobayashi H Hamaguchi (2003) Chem Lett 32 740 Occurrence Handle1:CAS:528:DC%2BD3sXmtlOrtr4%3D Occurrence Handle10.1246/cl.2003.740
JD Holbrey WM Reichert M Nieuwenhuyzen S Johnston KR Seddon RD Rogers (2003) Chem Commun 2003 1636 Occurrence Handle10.1039/b304543a Occurrence Handle1:CAS:528:DC%2BD3sXkvFKrsb8%3D
H Katayanagi S Hayashi H Hamaguchi K Nishikawa (2004) Chem Phys Lett 392 460 Occurrence Handle1:CAS:528:DC%2BD2cXltF2ktrs%3D Occurrence Handle10.1016/j.cplett.2004.04.125
J Bowers MC Vergara-Gutierrez JRP Webster (2004) Langmuir 20 309 Occurrence Handle1:CAS:528:DC%2BD3sXps1GlsLY%3D Occurrence Handle10.1021/la035495v
J Bowers CP Butts PJ Martin MC Vergara-Gutierrez RK Heenan (2004) Langmuir 20 2191 Occurrence Handle1:CAS:528:DC%2BD2cXpvFKitw%3D%3D Occurrence Handle10.1021/la035940m
S Takahashi LA Curtiss D Gosztola N Koura ML Saboungi (1995) Inorg Chem 34 2990 Occurrence Handle1:CAS:528:DyaK2MXls1yquro%3D Occurrence Handle10.1021/ic00115a029
S Hayashi R Ozawa H Hamaguchi (2003) Chem Lett 32 498 Occurrence Handle1:CAS:528:DC%2BD3sXkslCksr4%3D Occurrence Handle10.1246/cl.2003.498
K Nishikawa S Wang H Katayanagi S Hayashi H Hamaguchi Y Koga K Tozaki (2007) J Phys Chem B 111 4894 Occurrence Handle1:CAS:528:DC%2BD2sXitVyisbk%3D Occurrence Handle10.1021/jp0671852
Cambridge Crystallographic Data Centre, [C4 mim]Cl “Crystal (1)” [C4 mim]Br data are registered as CCDC deposition numbers 213959 and 213960, respectively, see http://www.ccdc.cam.ac.uk
CB Aakeröy TA Evans KR Seddon I Pálinkó (1999) New J Chem 23 145 Occurrence Handle10.1039/a809309a
JA van den Berg KR Seddon (2003) Crystal Growth Design 3 643 Occurrence Handle1:CAS:528:DC%2BD3sXlsFOhurs%3D Occurrence Handle10.1021/cg034083h
K Matsumoto R Hagiwara Z Mazej P Benkič B Žemva (2006) Solid State Sci 8 1250 Occurrence Handle1:CAS:528:DC%2BD28XptVGktLo%3D Occurrence Handle10.1016/j.solidstatesciences.2005.12.017
R Ozawa S Hayashi S Saha A Kobayashi H Hamaguchi (2003) Chem Lett 32 948 Occurrence Handle1:CAS:528:DC%2BD3sXotFOisbY%3D Occurrence Handle10.1246/cl.2003.948
Okajima H, Hamaguchi H (2006) Abstr. 231st ACS National Meeting, Atlanta, GA, US, March 26–30, 2006, IEC-015. Am Chem Soc, Washington, DC
Berg RW (2007) unpublished results
EA Turner CC Pye RD Singer (2003) J Phys Chem A 107 2277 Occurrence Handle1:CAS:528:DC%2BD3sXhslymsr4%3D Occurrence Handle10.1021/jp021694w
ER Talaty S Raja VJ Storhaug A Dölle WR Carper (2004) J Phys Chem B 108 13177 Occurrence Handle1:CAS:528:DC%2BD2cXmt12ks7s%3D Occurrence Handle10.1021/jp040199s
JH Antony D Mertens A Dölle P Wasserscheid WR Carper (2003) Chem Phys Chem 4 588 Occurrence Handle1:CAS:528:DC%2BD3sXkvFCgsbs%3D
JH Antony D Mertens T Breitenstein A Dölle P Wasserscheid WR Carper (2004) Pure Appl Chem 76 255 Occurrence Handle1:CAS:528:DC%2BD2cXhvFCjsrY%3D Occurrence Handle10.1351/pac200476010255
NE Heimer RE Del Sesto WR Carper (2004) Magn Reson Chem 42 71 Occurrence Handle1:CAS:528:DC%2BD2cXhsVyrsA%3D%3D Occurrence Handle10.1002/mrc.1318
NE Heimer RE Del Sesto Z Meng JS Wilkes WR Carper (2006) J Mol Liquids 124 84 Occurrence Handle1:CAS:528:DC%2BD28XhtV2mu7g%3D Occurrence Handle10.1016/j.molliq.2005.08.004
Y Umebayashi T Fujimori T Sukizaki M Asada K Fujii R Kanzaki S Ishiguro (2005) J Phys Chem A 109 8976 Occurrence Handle1:CAS:528:DC%2BD2MXhtVWhsL7L Occurrence Handle10.1021/jp053476j
A Downard MJ Earle C Hardacre SEJ McMath M Nieuwenhuyzen SJ Teat (2004) Chem Mater 16 43 Occurrence Handle1:CAS:528:DC%2BD3sXptlOhur8%3D Occurrence Handle10.1021/cm034344a
G Giraud CM Gordon IR Dunkin K Wynne (2003) J Chem Phys 119 464 Occurrence Handle1:CAS:528:DC%2BD3sXkvVShtLc%3D Occurrence Handle10.1063/1.1578056
A Triolo A Mandanici O Russina V Rodriguez-Mora M Cutroni C Hardacre M Nieuwenhuyzen HJ Bleif L Keller MA Ramos (2006) J Phys Chem B 110 21357 Occurrence Handle1:CAS:528:DC%2BD28XpvVCht70%3D Occurrence Handle10.1021/jp062895t
S Shigeto H Hamaguchi (2006) Chem Phys Lett 427 329 Occurrence Handle1:CAS:528:DC%2BD28XotFWrtr8%3D Occurrence Handle10.1016/j.cplett.2006.07.004
a) Morrow TI, Maginn EJ (2002) J Phys Chem B 106: 12807; b) Erratum: Morrow TI, Maginn EJ (2003) J Phys Chem B 107: 9160
TI Morrow EJ Maginn (2003) ACS Symp Ser 2003 (Ionic Liquids as Green Solvents) 856 1624
JK Shah EJ Maginn (2004) Fluid Phase Equilibria 195–203 222
S Hayashi H Hamaguchi (2004) Chem Lett 33 1590 Occurrence Handle1:CAS:528:DC%2BD2cXhtFaitL%2FJ Occurrence Handle10.1246/cl.2004.1590
S Hayashi S Saha H Hamaguchi (2006) IEEE Trans Magnetics 42 12 Occurrence Handle1:CAS:528:DC%2BD28Xmt1Gntw%3D%3D Occurrence Handle10.1109/TMAG.2005.854875
Hamaguchi H, Saha S, Ozawa R, Hayashi S (2005) ACS Symp Ser 901 (Ionic Liquids IIIA: Fundamentals, Progress, Challenges, Opportunities) 68
JN Canongia Lopes MF Costa Gomes AAH Pádua (2006) J Phys Chem B 110 16816 Occurrence Handle10.1021/jp063603r Occurrence Handle1:CAS:528:DC%2BD28XnvVKiurg%3D
JN Canongia Lopes J Deschamps AAH Pádua (2004) J Phys Chem B 108 2038 Occurrence Handle10.1021/jp0362133 Occurrence Handle1:CAS:528:DC%2BD2cXjslWlsA%3D%3D
JN Canongia Lopes AAH Pádua (2004) J Phys Chem B 108 16893 Occurrence Handle10.1021/jp0476545 Occurrence Handle1:CAS:528:DC%2BD2cXnvFGgtbY%3D
JNA Canongia Lopes AAH Pádua (2006) J Phys Chem B 110 7485 Occurrence Handle10.1021/jp057533k Occurrence Handle1:CAS:528:DC%2BD28Xis1Wlsbk%3D
JNA Canongia Lopes AAH Pádua (2006) J Phys Chem B 110 3330 Occurrence Handle1:CAS:528:DC%2BD28XoslaksA%3D%3D Occurrence Handle10.1021/jp056006y
J De Andrade ES Böes H Stassen (2002) J Phys Chem B 106 3546 Occurrence Handle1:CAS:528:DC%2BD38Xhsl2ntL8%3D Occurrence Handle10.1021/jp014229s
J De Andrade ES Böes H Stassen (2002) J Phys Chem B 106 13344 Occurrence Handle1:CAS:528:DC%2BD38XovFCnt78%3D Occurrence Handle10.1021/jp0216629
CJ Margulis HA Stern BJ Berne (2002) J Phys Chem B 106 12017 Occurrence Handle1:CAS:528:DC%2BD38XotFGgu7w%3D Occurrence Handle10.1021/jp021392u
MG Del Pópolo GA Voth (2004) J Phys Chem B 108 1744 Occurrence Handle10.1021/jp0364699 Occurrence Handle1:CAS:528:DC%2BD2cXksFynsw%3D%3D
T Yan CJ Burnham MG Del Pópolo GA Voth (2004) J Phys Chem B 108 11877 Occurrence Handle1:CAS:528:DC%2BD2cXlslertrs%3D Occurrence Handle10.1021/jp047619y
Z Liu S Huang W Wang (2004) J Phys Chem B 108 12978 Occurrence Handle1:CAS:528:DC%2BD2cXmt1Sns70%3D Occurrence Handle10.1021/jp048369o
SM Urahata MCC Ribeiro (2004) J Chem Phys 120 1855 Occurrence Handle1:CAS:528:DC%2BD2cXmslClsA%3D%3D Occurrence Handle10.1063/1.1635356
H Miki S Hayashi H Kikura H Hamaguchi (2006) J Raman Spectrosc 37 1242 Occurrence Handle1:CAS:528:DC%2BD28Xht1Gkt7nF Occurrence Handle10.1002/jrs.1646
S Saha H Hamaguchi (2006) J Phys Chem B 110 2777 Occurrence Handle1:CAS:528:DC%2BD28Xnt1Cnsg%3D%3D Occurrence Handle10.1021/jp053817t
NE Heimer JS Wilkes PG Wahlbeck WR Carper (2006) J Phys Chem A 110 868 Occurrence Handle1:CAS:528:DC%2BD28XmvVamsg%3D%3D Occurrence Handle10.1021/jp056045+
I Rey P Johansson J Lindgren JC Lassegues J Grondin L Servant (1998) J Phys Chem A 102 3249 Occurrence Handle1:CAS:528:DyaK1cXivFCit7c%3D Occurrence Handle10.1021/jp980375v
I Rey JC Lassegues J Grondin L Servant (1998) Electrochim Acta 43 1505 Occurrence Handle1:CAS:528:DyaK1cXjsFyhsrs%3D Occurrence Handle10.1016/S0013-4686(97)10092-5
K Fujii T Fujimori T Takamuku R Kanzaki Y Umebayashi S Ishiguro (2006) J Phys Chem B 110 8179 Occurrence Handle1:CAS:528:DC%2BD28XjtV2jtbs%3D Occurrence Handle10.1021/jp0612477
K Matsumoto R Hagiwara O Tamada (2006) Solid State Sci 8 1103 Occurrence Handle1:CAS:528:DC%2BD28XptVGktLo%3D Occurrence Handle10.1016/j.solidstatesciences.2005.12.017
NL Lancaster PA Salter T Welton GB Young (2002) J Org Chem 67 8855 Occurrence Handle1:CAS:528:DC%2BD38XosFCqtbw%3D Occurrence Handle10.1021/jo026113d
E Dal NL Lancaster (2005) Org Biomol Chem 3 682 Occurrence Handle1:CAS:528:DC%2BD2MXht1KqtrY%3D Occurrence Handle10.1039/b417152g
AR Choudhury N Winterton A Steiner AI Cooper KA Johnson (2005) J Am Chem Soc 127 16792 Occurrence Handle1:CAS:528:DC%2BD2MXhtFKrt73E Occurrence Handle10.1021/ja055956u
AI Bhatt NW Duffy D Collison I May RG Lewin (2006) Inorg Chem 45 1677 Occurrence Handle1:CAS:528:DC%2BD28XjsFCmtQ%3D%3D Occurrence Handle10.1021/ic051750i
JD Holbrey MB Turner WM Reichert DR Rogers (2003) Green Chem 5 731 Occurrence Handle1:CAS:528:DC%2BD3sXpsFymsLs%3D Occurrence Handle10.1039/b311717k
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Berg, R. Raman Spectroscopy and Ab-Initio Model Calculations on Ionic Liquids. Monatsh. Chem. 138, 1045–1075 (2007). https://doi.org/10.1007/s00706-007-0760-9
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DOI: https://doi.org/10.1007/s00706-007-0760-9