Thermodynamics Research Center / ThermoML | Thermochimica Acta

Thermodynamics of hydrogen bonding and van der Waals interactions of organic solutes in solutions of imidazolium based ionic liquids: "structure-property" relationships

Varfolomeev, M. A.[Mikhail A.], Khachatrian, A. A.[Artashes A.], Akhmadeev, B. S.[Bulat S.], Solomonov, B. N.[Boris N.]
Thermochim. Acta 2016, 633, 12-23
ABSTRACT
In the present work thermochemistry of intermolecular interactions of organic compounds in solu-tions of imidazolium based ionic liquids (ILs) has been studied using solution calorimetry method.Enthalpies of solution at infinite dilution of non-polar (alkanes, aromatic hydrocarbons) and polar(alcohols, amides, and etc.) organic solutes in two ionic liquids 1-butyl-3-methylimidazolium tetrafluo-roborate and 1-butyl-3-methylimidazolium trifluoromethanesulfonate were measured at 298.15 K. Thescale of van der Waals interactions of imidazolium based ILs has been proposed on the basis of solu-tion enthalpies of n-alkanes in their media. The effect of the cation and anion structure of ILs on theenthalpies of solvation was analyzed. Enthalpies of hydrogen bonding of organic solutes with imida-zolium based ILs were determined. It has been shown that these values are close to zero for protonacceptor solutes. At the same time, enthalpies of hydrogen bonding of proton donor solutes with ionicliquids are increased depending the anion: tetrafluoroborate . bis(trifluoromethylsulfonyl)imide less than 2-(2-methoxyethoxy)ethyl sulfate less than trifluoromethanesulfonate. Enthalpies of van der Waals interactions andhydrogen bonding in the solutions of imidazolium based ionic liquids were compared with the same datafor molecular solvents.
Compounds
# Formula Name
1 C8H15BF4N2 1-butyl-3-methylimidazolium tetrafluoroborate
2 C9H15F3N2O3S 1-butyl-3-methylimidazolium trifluoromethanesulfonate
3 C3H6O acetone
4 C2H3N acetonitrile
5 C6H7N aniline
6 C6H6 benzene
7 C4H10O butan-1-ol
8 C2H6OS dimethyl sulfoxide
9 C3H7NO dimethylformamide
10 C2H6O ethanol
11 C2H6O2 1,2-ethanediol
12 CH3NO formamide
13 C7H16 heptane
14 CH4O methanol
15 C3H8O2 2-methoxyethan-1-ol
16 C9H20 nonane
17 C8H18 octane
18 C3H8O propan-1-ol
19 C4H6O3 4-methyl-1,3-dioxolan-2-one
20 C4H8O tetrahydrofuran
21 C7H8 toluene
22 CHCl3 trichloromethane
23 C8H10 1,3-dimethylbenzene
Datasets
The table above is generated from the ThermoML associated json file (link above). POMD and RXND refer to PureOrMixture and Reaction Datasets. The compound numbers are included in properties, variables, and phases, if specificied; the numbers refer to the table of compounds on the left.
Type Compound-# Property Variable Constraint Phase Method #Points
  • POMD
  • 4
  • 1
  • Molar enthalpy of solution, kJ/mol ; Liquid
  • Mole fraction - 4; Liquid
  • Pressure, kPa; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Titration calorimetry
  • 1
  • POMD
  • 3
  • 1
  • Molar enthalpy of solution, kJ/mol ; Liquid
  • Mole fraction - 3; Liquid
  • Pressure, kPa; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Titration calorimetry
  • 1
  • POMD
  • 5
  • 1
  • Molar enthalpy of solution, kJ/mol ; Liquid
  • Mole fraction - 5; Liquid
  • Pressure, kPa; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Titration calorimetry
  • 1
  • POMD
  • 6
  • 1
  • Molar enthalpy of solution, kJ/mol ; Liquid
  • Mole fraction - 6; Liquid
  • Pressure, kPa; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Titration calorimetry
  • 1
  • POMD
  • 7
  • 1
  • Molar enthalpy of solution, kJ/mol ; Liquid
  • Mole fraction - 7; Liquid
  • Pressure, kPa; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Titration calorimetry
  • 1
  • POMD
  • 8
  • 1
  • Molar enthalpy of solution, kJ/mol ; Liquid
  • Mole fraction - 8; Liquid
  • Pressure, kPa; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Titration calorimetry
  • 1
  • POMD
  • 9
  • 1
  • Molar enthalpy of solution, kJ/mol ; Liquid
  • Mole fraction - 9; Liquid
  • Pressure, kPa; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Titration calorimetry
  • 1
  • POMD
  • 10
  • 1
  • Molar enthalpy of solution, kJ/mol ; Liquid
  • Mole fraction - 10; Liquid
  • Pressure, kPa; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Titration calorimetry
  • 1
  • POMD
  • 11
  • 1
  • Molar enthalpy of solution, kJ/mol ; Liquid
  • Mole fraction - 11; Liquid
  • Pressure, kPa; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Titration calorimetry
  • 1
  • POMD
  • 12
  • 1
  • Molar enthalpy of solution, kJ/mol ; Liquid
  • Mole fraction - 12; Liquid
  • Pressure, kPa; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Titration calorimetry
  • 1
  • POMD
  • 13
  • 1
  • Molar enthalpy of solution, kJ/mol ; Liquid
  • Mole fraction - 13; Liquid
  • Pressure, kPa; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Titration calorimetry
  • 1
  • POMD
  • 14
  • 1
  • Molar enthalpy of solution, kJ/mol ; Liquid
  • Mole fraction - 14; Liquid
  • Pressure, kPa; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Titration calorimetry
  • 1
  • POMD
  • 15
  • 1
  • Molar enthalpy of solution, kJ/mol ; Liquid
  • Mole fraction - 15; Liquid
  • Pressure, kPa; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Titration calorimetry
  • 1
  • POMD
  • 16
  • 1
  • Molar enthalpy of solution, kJ/mol ; Liquid
  • Mole fraction - 16; Liquid
  • Pressure, kPa; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Titration calorimetry
  • 1
  • POMD
  • 17
  • 1
  • Molar enthalpy of solution, kJ/mol ; Liquid
  • Mole fraction - 17; Liquid
  • Pressure, kPa; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Titration calorimetry
  • 1
  • POMD
  • 18
  • 1
  • Molar enthalpy of solution, kJ/mol ; Liquid
  • Mole fraction - 18; Liquid
  • Pressure, kPa; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Titration calorimetry
  • 1
  • POMD
  • 19
  • 1
  • Molar enthalpy of solution, kJ/mol ; Liquid
  • Mole fraction - 19; Liquid
  • Pressure, kPa; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Titration calorimetry
  • 1
  • POMD
  • 21
  • 1
  • Molar enthalpy of solution, kJ/mol ; Liquid
  • Mole fraction - 21; Liquid
  • Pressure, kPa; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Titration calorimetry
  • 1
  • POMD
  • 22
  • 1
  • Molar enthalpy of solution, kJ/mol ; Liquid
  • Mole fraction - 22; Liquid
  • Pressure, kPa; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Titration calorimetry
  • 1
  • POMD
  • 23
  • 1
  • Molar enthalpy of solution, kJ/mol ; Liquid
  • Mole fraction - 23; Liquid
  • Pressure, kPa; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Titration calorimetry
  • 1
  • POMD
  • 4
  • 2
  • Molar enthalpy of solution, kJ/mol ; Liquid
  • Mole fraction - 4; Liquid
  • Pressure, kPa; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Titration calorimetry
  • 1
  • POMD
  • 3
  • 2
  • Molar enthalpy of solution, kJ/mol ; Liquid
  • Mole fraction - 3; Liquid
  • Pressure, kPa; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Titration calorimetry
  • 1
  • POMD
  • 5
  • 2
  • Molar enthalpy of solution, kJ/mol ; Liquid
  • Mole fraction - 5; Liquid
  • Pressure, kPa; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Titration calorimetry
  • 1
  • POMD
  • 6
  • 2
  • Molar enthalpy of solution, kJ/mol ; Liquid
  • Mole fraction - 6; Liquid
  • Pressure, kPa; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Titration calorimetry
  • 1
  • POMD
  • 7
  • 2
  • Molar enthalpy of solution, kJ/mol ; Liquid
  • Mole fraction - 7; Liquid
  • Pressure, kPa; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Titration calorimetry
  • 1
  • POMD
  • 8
  • 2
  • Molar enthalpy of solution, kJ/mol ; Liquid
  • Mole fraction - 8; Liquid
  • Pressure, kPa; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Titration calorimetry
  • 1
  • POMD
  • 9
  • 2
  • Molar enthalpy of solution, kJ/mol ; Liquid
  • Mole fraction - 9; Liquid
  • Pressure, kPa; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Titration calorimetry
  • 1
  • POMD
  • 10
  • 2
  • Molar enthalpy of solution, kJ/mol ; Liquid
  • Mole fraction - 10; Liquid
  • Pressure, kPa; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Titration calorimetry
  • 1
  • POMD
  • 11
  • 2
  • Molar enthalpy of solution, kJ/mol ; Liquid
  • Mole fraction - 11; Liquid
  • Pressure, kPa; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Titration calorimetry
  • 1
  • POMD
  • 12
  • 2
  • Molar enthalpy of solution, kJ/mol ; Liquid
  • Mole fraction - 12; Liquid
  • Pressure, kPa; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Titration calorimetry
  • 1
  • POMD
  • 14
  • 2
  • Molar enthalpy of solution, kJ/mol ; Liquid
  • Mole fraction - 14; Liquid
  • Pressure, kPa; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Titration calorimetry
  • 1
  • POMD
  • 15
  • 2
  • Molar enthalpy of solution, kJ/mol ; Liquid
  • Mole fraction - 15; Liquid
  • Pressure, kPa; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Titration calorimetry
  • 1
  • POMD
  • 18
  • 2
  • Molar enthalpy of solution, kJ/mol ; Liquid
  • Mole fraction - 18; Liquid
  • Pressure, kPa; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Titration calorimetry
  • 1
  • POMD
  • 19
  • 2
  • Molar enthalpy of solution, kJ/mol ; Liquid
  • Mole fraction - 19; Liquid
  • Pressure, kPa; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Titration calorimetry
  • 1
  • POMD
  • 20
  • 2
  • Molar enthalpy of solution, kJ/mol ; Liquid
  • Mole fraction - 20; Liquid
  • Pressure, kPa; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Titration calorimetry
  • 1
  • POMD
  • 22
  • 2
  • Molar enthalpy of solution, kJ/mol ; Liquid
  • Mole fraction - 22; Liquid
  • Pressure, kPa; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Titration calorimetry
  • 1