Does the cation really matter? The effect of modifying an ionic liquid cation on an SN2 process

被引:43
|
作者
Tanner, Eden E. L. [1 ]
Yau, Hon Man [1 ]
Hawker, Rebecca R. [1 ]
Croft, Anna K. [2 ,3 ]
Harper, Jason B. [1 ]
机构
[1] Univ New S Wales, Sch Chem, Sydney, NSW 2052, Australia
[2] Univ Nottingham, Dept Chem & Environm Engn, Nottingham NG7 2RD, England
[3] Univ Wales, Sch Chem, Bangor LL57 2UW, Gwynedd, Wales
基金
澳大利亚研究理事会;
关键词
MOLECULAR-DYNAMICS; PURE IMIDAZOLIUM; SOLVENT; SUBSTITUTION; COMPLEX; CATALYST; SALTS; WATER;
D O I
10.1039/c3ob41038b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The rate of reaction of a Menschutkin process in a range of ionic liquids with different cations was investigated, with temperature-dependent kinetic data giving access to activation parameters for the process in each solvent. These data, along with molecular dynamics simulations, demonstrate the importance of accessibility of the charged centre on the cation and that the key interactions are of a generalised electrostatic nature.
引用
收藏
页码:6170 / 6175
页数:6
相关论文
共 50 条
  • [1] Effect of Modifying the Anion of an Ionic Liquid on the Outcome of an SN2 Process
    Keaveney, Sinead T.
    Francis, Dominic V.
    Cao, Winnie
    Haines, Ronald S.
    Harper, Jason B.
    AUSTRALIAN JOURNAL OF CHEMISTRY, 2015, 68 (01) : 31 - 35
  • [2] Effect of cation size of binary cation ionic liquid mixtures on capacitive energy storage
    Seltmann, Anna
    Verkholyak, Taras
    Golowicz, Dariusz
    Pamete, Emmanuel
    Kuzmak, Andrij
    Presser, Volker
    Kondrat, Svyatoslav
    JOURNAL OF MOLECULAR LIQUIDS, 2023, 391
  • [3] Simulations of imidazolium ionic liquids: when does the cation charge distribution matter?
    Lynden-Bell, R. M.
    Youngs, T. G. A.
    JOURNAL OF PHYSICS-CONDENSED MATTER, 2009, 21 (42)
  • [4] Effect of the cation and anion of the ionic liquid on desulfurization of model fuels
    Domanska, Urszula
    Wlazlo, Michal
    FUEL, 2014, 134 : 114 - 125
  • [5] The Effect of Lengthening Cation Ether Tails On Ionic Liquid Properties
    Lall-Ramnarine, Sharon I.
    Rodriguez, Chanele
    Fernandez, Rahonel
    Zmich, Nicole
    Fernandez, Eddie D.
    Dhiman, Surajdevprakash B.
    Wishart, James F.
    MOLTEN SALTS AND IONIC LIQUIDS 20, 2016, 75 (15): : 215 - 232
  • [6] Charge Screening in the SN2 Reaction of Charged Electrophiles and Charged Nucleophiles: An Ionic Liquid Effect
    Hallett, Jason P.
    Liotta, Charles L.
    Ranieri, Giuseppe
    Welton, Tom
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (05): : 1864 - 1868
  • [7] Ionic Liquid Based Aqueous Biphasic Systems with Controlled pH: The Ionic Liquid Cation Effect
    Ventura, Sonia P. M.
    Sousa, Silvia G.
    Serafim, Luisa S.
    Lima, Alvaro S.
    Freire, Mara G.
    Coutinho, Joao A. P.
    JOURNAL OF CHEMICAL AND ENGINEERING DATA, 2011, 56 (11): : 4253 - 4260
  • [8] Cation does matter: how cationic structure affects the dissolution of cellulose in ionic liquids
    Lu, Benlian
    Xu, Airong
    Wang, Jianji
    GREEN CHEMISTRY, 2014, 16 (03) : 1326 - 1335
  • [9] Effect of hydration of a room temperature ionic liquid on the cation-cation interaction of UO22+ and NpO2+ ions
    Verma, Parveen Kumar
    Bhattacharyya, Arunasis
    Mohapatra, Prasanta Kumar
    NEW JOURNAL OF CHEMISTRY, 2023, 47 (15) : 7391 - 7398
  • [10] The effect of ionic liquid cation and anion combinations on the macromolecular structure of lignins
    George, Anthe
    Tran, Kim
    Morgan, Trevor J.
    Benke, Peter I.
    Berrueco, Cesar
    Lorente, Esther
    Wu, Ben C.
    Keasling, Jay D.
    Simmons, Blake A.
    Holmes, Bradley M.
    GREEN CHEMISTRY, 2011, 13 (12) : 3375 - 3385