Polarity and hydrogen-bond-donor strength for some ionic liquids: Effect of alkyl chain length on the pyrrolidinium cation

被引：62
作者：
Lee, Jong-Min [1 ]
Prausnitz, John M. [2 ,3 ]
机构：
[1] Nanyang Technol Univ, Sch Chem & Biomed Engn, Singapore, Singapore
[2] Univ Calif Berkeley, Dept Chem Engn, Berkeley, CA 94720 USA
[3] Univ Calif Berkeley, Lawrence Berkeley Lab, Div Chem Sci, Berkeley, CA 94720 USA
来源：
CHEMICAL PHYSICS LETTERS | 2010年 / 492卷 / 1-3期
关键词：
DIELS-ALDER REACTION; 1-BUTYL-3-METHYLIMIDAZOLIUM HEXAFLUOROPHOSPHATE; PHYSICOCHEMICAL PROPERTIES; SOLVENT POLARITIES; TEMPERATURE; PYRIDINIUM; DYES;
D O I：
10.1016/j.cplett.2010.03.086
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
Several ionic liquids were synthesized to investigate the influence of alkyl chain length and functional group attached to the cation on polarity and on three Kamlet-Taft parameters. Results are reported for polarity, dipolarity/polarizability, hydrogen-bond-donating acidity, and hydrogen-bond-accepting basicity in the range 25-65 degrees C. A long alkyl chain (1-octyl) on the pyrrolidinium cation leads to high polarity and high hydrogen-bond-donating acidity. At 25 degrees C, the hydrogen-bond-donating acidity for 1-methyl-1- octyl pyrrolidinium bis(trifluoromethansulfonyl)imide is close to that for water. (C) 2010 Elsevier B.V. All rights reserved.
引用
收藏
页码：55 / 59
页数：5
相关论文
共 23 条
  • [1] Structure and properties of high stability geminal dicationic ionic liquids
    Anderson, JL
    Ding, RF
    Ellern, A
    Armstrong, DW
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (02) : 593 - 604
  • [2] Temperature-dependent microscopic solvent properties of 'dry' and 'wet' 1-butyl-3-methylimidazolium hexafluorophosphate: correlation with ET(30) and Kamlet-Taft polarity scales
    Baker, SN
    Baker, GA
    Bright, FV
    [J]. GREEN CHEMISTRY, 2002, 4 (02) : 165 - 169
  • [3] The cybotactic region surrounding fluorescent probes dissolved in 1-butyl-3-methylimidazolium hexafluorophosphate: Effects of temperature and added carbon dioxide
    Baker, SN
    Baker, GA
    Kane, MA
    Bright, FV
    [J]. JOURNAL OF PHYSICAL CHEMISTRY B, 2001, 105 (39) : 9663 - 9668
  • [4] A rationalization of the solvent effect on the Diels-Alder reaction in ionic liquids using multiparameter linear solvation energy relationships
    Bini, Riccardo
    Chiappe, Cinzia
    Mestre, Veronica Llopsis
    Pomelli, Christian Silvio
    Welton, Thomas
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (14) : 2522 - 2529
  • [5] Borra EF, 2007, NATURE, V447, P979, DOI 10.1038/nature05909
  • [6] Solvent-solute interactions in ionic liquids
    Crowhurst, L
    Mawdsley, PR
    Perez-Arlandis, JM
    Salter, PA
    Welton, T
    [J]. PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2003, 5 (13) : 2790 - 2794
  • [7] Expanding the polarity range of ionic liquids
    Dzyuba, SV
    Bartsch, RA
    [J]. TETRAHEDRON LETTERS, 2002, 43 (26) : 4657 - 4659
  • [8] Ionic liquid-polymer gel electrolytes
    Fuller, J
    Breda, AC
    Carlin, RT
    [J]. JOURNAL OF THE ELECTROCHEMICAL SOCIETY, 1997, 144 (04) : L67 - L70
  • [9] GORDON JE, 1969, TECHNIQUES METHODS O, V1, P55
  • [10] Contrasting Thermosolvatochromic Trends in Pyridinium-, Pyrrolidinium-, and Phosphonium-Based Ionic Liquids
    Khupse, Nageshwar D.
    Kumar, Anil
    [J]. JOURNAL OF PHYSICAL CHEMISTRY B, 2010, 114 (01) : 376 - 381
123