Thermodynamics Research Center / ThermoML | Journal of Chemical Thermodynamics

Thermodynamic properties of ethanol solution of chiral camphors and its derivatives

Kimura, T.[Takayoshi], Iwama, S.[Sekai], Kido, S.[Satoko], Khan, M. A.[Mohammad Abdullah]
J. Chem. Thermodyn. 2009, 41, 10, 1170-1177
ABSTRACT
Enthalpies of mixing and the densities of ethanol solution of R- and S-enantiomers of camphor, 10-camphorsulfonamide, 10-camphorsulfonic acid, camphorquinone, and 10-camphorsulfonyl chloride have been measured for a wide range of mole fractions of heterochiral components at 298.15 K. Enthalpies of mixing were exothermic for all concentrations and heterochiral solutions were more stable than each of the homochiral solutions. Enthalpic stabilization of mixing of heterochiral solutions was increased with a decreasing concentration of all the camphor derivatives measured. The sequence of enthalpic stabilization on mixing was 10-camphorsulfonyl chloride, 10-camphorsulfonic acid, 10-camphorsulfonamide, camphor, and camphorquinone. Apparent molar volumes were determined and excess volumes of mixing of heterochiral solutions were small and negative. Enthalpic stabilizations were found to be dependent on dipole dipole interaction between solutes and solvents.
Compounds
# Formula Name
1 C10H16O d-camphor
2 C10H16O (1S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one
3 C10H17NO3S (1R)-(-)-10-camphorsulfonamide
4 C10H17NO3S (1S)-(+)-10-camphorsulfonamide
5 C10H16O4S (1R)-(-)-10-camphorsulfonic acid
6 C10H16O4S (1S)-(+)-10-camphorsulfonic acid
7 C10H14O2 (-)-camphorquinone
8 C10H14O2 (+)-camphorquinone
9 C10H15ClO3S (1R)-(-)-10-camphorsulfonyl chloride
10 C10H15ClO3S d-10-camphorsulfonyl chloride
11 C2H6O ethanol
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
  • 11
  • 1
  • Mass density, kg/m3 ; Liquid
  • Mole fraction - 1; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Vibrating tube method
  • 5
  • POMD
  • 11
  • 2
  • Mass density, kg/m3 ; Liquid
  • Mole fraction - 2; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Vibrating tube method
  • 5
  • POMD
  • 11
  • 3
  • Mass density, kg/m3 ; Liquid
  • Mole fraction - 3; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Vibrating tube method
  • 4
  • POMD
  • 11
  • 4
  • Mass density, kg/m3 ; Liquid
  • Mole fraction - 4; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Vibrating tube method
  • 4
  • POMD
  • 11
  • 5
  • Mass density, kg/m3 ; Liquid
  • Mole fraction - 5; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Vibrating tube method
  • 4
  • POMD
  • 11
  • 6
  • Mass density, kg/m3 ; Liquid
  • Mole fraction - 6; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Vibrating tube method
  • 4
  • POMD
  • 11
  • 7
  • Mass density, kg/m3 ; Liquid
  • Mole fraction - 7; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Vibrating tube method
  • 4
  • POMD
  • 11
  • 8
  • Mass density, kg/m3 ; Liquid
  • Mole fraction - 8; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Vibrating tube method
  • 4
  • POMD
  • 11
  • 9
  • Mass density, kg/m3 ; Liquid
  • Mole fraction - 9; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Vibrating tube method
  • 4
  • POMD
  • 11
  • 10
  • Mass density, kg/m3 ; Liquid
  • Mole fraction - 10; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Vibrating tube method
  • 4
  • POMD
  • 11
  • 2
  • 1
  • Excess molar enthalpy (molar enthalpy of mixing), kJ/mol ; Liquid
  • Mass fraction - 11; Liquid
  • Solvent: Amount ratio of component to other component of binary solvent - 2; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Flow calorimetry
  • 40
  • POMD
  • 11
  • 4
  • 3
  • Excess molar enthalpy (molar enthalpy of mixing), kJ/mol ; Liquid
  • Mass fraction - 11; Liquid
  • Solvent: Amount ratio of component to other component of binary solvent - 4; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Flow calorimetry
  • 40
  • POMD
  • 11
  • 6
  • 5
  • Excess molar enthalpy (molar enthalpy of mixing), kJ/mol ; Liquid
  • Mass fraction - 11; Liquid
  • Solvent: Amount ratio of component to other component of binary solvent - 6; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Flow calorimetry
  • 40
  • POMD
  • 11
  • 10
  • 9
  • Excess molar enthalpy (molar enthalpy of mixing), kJ/mol ; Liquid
  • Mass fraction - 11; Liquid
  • Solvent: Amount ratio of component to other component of binary solvent - 10; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Flow calorimetry
  • 45
  • POMD
  • 11
  • 8
  • 7
  • Excess molar enthalpy (molar enthalpy of mixing), kJ/mol ; Liquid
  • Mass fraction - 11; Liquid
  • Solvent: Amount ratio of component to other component of binary solvent - 7; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Flow calorimetry
  • 30