Thermodynamics Research Center / ThermoML | Journal of Chemical Thermodynamics

Thermodynamic study of phase transitions in methyl esters of ortho-, meta-, and para-aminobenzoic acids

Almeida, A. R. R. P.[Ana R.R.P.], Monte, M. J. S.[Manuel J. S.]
J. Chem. Thermodyn. 2012, 53, 100-107
ABSTRACT
A static method based on capacitance gauges was used to measure the vapor pressures of the condensed phases of the methyl esters of the three aminobenzoic acids. For methyl o-aminobenzoate the vapor pressures of the liquid phase were measured in the range (285.4 to 369.5) K. For the meta and para isomers vapor pressures of both crystalline and liquid phases were measured in the ranges (308.9 to 376.6) K, and (332.9 to 428.0) K, respectively. Vapor pressures of the latter compound were also measured using the Knudsen effusion method in the temperature range (319.1 to 341.2) K. From the dependence of the vapor pressures on the temperature, the standard molar enthalpies and entropies of sublimation and of vaporization were derived. Differential scanning calorimetry was used to measure the temperatures and molar enthalpies of fusion of the three isomers. The results enabled the estimation of the enthalpy of the intermolecular (N H. . .O) hydrogen bond in the crystalline methyl p-aminobenzoate. A correlation relating the temperature of fusion and the enthalpy and Gibbs energy of sublimation of benzene, methyl benzoates and benzoic acids was derived.
Compounds
# Formula Name
1 C8H9NO2 methyl 4-aminobenzoate
2 C8H9NO2 methyl 3-aminobenzoate
3 C8H9NO2 methyl 2-aminobenzoate
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
  • 1
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DSC
  • 1
  • POMD
  • 1
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 1
  • Vapor or sublimation pressure, kPa ; Crystal
  • Temperature, K; Crystal
  • Crystal
  • Gas
  • Calculated from knudsen effusion weight loss
  • 11
  • POMD
  • 1
  • Vapor or sublimation pressure, kPa ; Crystal
  • Temperature, K; Crystal
  • Crystal
  • Gas
  • Closed cell (Static) method
  • 25
  • POMD
  • 1
  • Vapor or sublimation pressure, kPa ; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Gas
  • Closed cell (Static) method
  • 35
  • POMD
  • 2
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DSC
  • 1
  • POMD
  • 2
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 2
  • Vapor or sublimation pressure, kPa ; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Gas
  • Closed cell (Static) method
  • 36
  • POMD
  • 2
  • Vapor or sublimation pressure, kPa ; Crystal
  • Temperature, K; Crystal
  • Crystal
  • Gas
  • Closed cell (Static) method
  • 11
  • POMD
  • 3
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DSC
  • 1
  • POMD
  • 3
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 3
  • Vapor or sublimation pressure, kPa ; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Gas
  • Closed cell (Static) method
  • 45