Thermodynamics Research Center / ThermoML | Journal of Chemical and Engineering Data

The Joining of Measurement and Prediction: The Enthalpy of Formation of 1,4-Cubanedicarboxylic Acid

Roux, M. V.[MarIa Victoria], Martinez, G.[Gwendolyn], Notario, R.[Rafael], Kini, S.[Sandeep], Chickos, J. S.[James S.], Liebman, J. F.[Joel F.]
J. Chem. Eng. Data 2011, 56, 4, 1220-1228
ABSTRACT
This study is a multidisciplinary contribution to the thermochemistry of 1,4-cubanedicarboxylic acid (pentacyclo[4.2.0.02,5.03,8.04,7]octane-1,4-dicarboxylic acid). An isoperibolic static microbomb calorimeter was used to determine the enthalpy of formation in the condensed phase at T = 298.15 K as ?fHmdeg (cr) = (-355.9 +- 11.7) kJ*mol-1. The enthalpy of sublimation was obtained by combining the vaporization enthalpy evaluated by correlation-gas chromatography and the fusion enthalpy measured by differential scanning calorimetry and adjusted to T = 298.15 K, which afforded the value ?subHm(298.15 K) = (126.5 +- 9.0) kJ*mol-1. Combination of these two enthalpies gave ?fHmdeg (g, 298.15 K) = (-229.4 +- 14.8) kJ*mol-1. Additionally the enthalpy of sublimation of 1-adamantanecarboxylic acid (tricyclo[3.3.1.13,7]decane-1-carboxylic acid) was determined as ?subHm(298.15 K) = (98.7 +- 4.5) kJ*mol-1. By means of theoretical calculations using isodesmic reactions, the enthalpy of formation of 2,6-cuneanedicarboxylic acid (pentacyclo[3.3.0.02,4.03,7.06,8]octane-2,6-dicarboxylic acid) was calculated. Strain energies of cubane and cuneane dicarboxylic acids were also calculated.
Compounds
# Formula Name
1 CO2 carbon dioxide
2 H2O water
3 O2 oxygen
4 C10H8O4 pentacyclo[4.2.0.02,5.03,8.04,7]octane-1,4-dicarboxylic acid
5 C11H16O2 tricyclo[3.3.1.1(3,7)]decane-1-carboxylic acid
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
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DSC
  • 1
  • POMD
  • 4
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 4
  • Molar enthalpy of vaporization or sublimation, kJ/mol ; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Gas
  • Correlation gas chromatography
  • 1
  • POMD
  • 5
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DSC
  • 1
  • POMD
  • 5
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 5
  • Molar enthalpy of vaporization or sublimation, kJ/mol ; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Gas
  • Correlation gas chromatography
  • 1
  • RXND
  • 4
  • 1
  • 2
  • 3
  • Specific internal energy of reaction at constant volume, J/g
  • Static bomb calorimetry
  • 1