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

Validation of the Vaporization Enthalpies of Some Simple Aliphatic Amides and Their Use in the Evaluation of the Vaporization Enthalpy of Valpromide and Valnoctamide

Gutterman, A.[Alexis], Rath, N.[Nigam], Chickos, J.[James]
J. Chem. Eng. Data 2013, 58, 3, 749-757
ABSTRACT
The vaporization enthalpy of valpromide and both diasteriomers of valnoctamide have been evaluated by correlation gas chromatography as has the fusion and sublimation enthalpy of valpromide. Values of [(18.6 +- 1.8), (83.6 +- 2.5), and (102.2 +- 3.1)] kJ*mol 1 at T/K = 298.15 have been evaluated for the fusion, vaporization, and sublimation enthalpies of valpromide (2-ethylpentanamide), respectively, and [(82.3 +- 2.5) and (82.7 +- 2.5)] kJ*mol 1 have been obtained for the vaporization enthalpy of valnoctamide ((2SR,3SR) and (2SR,3RS) 2-ethyl-3-methylpentanamide), respectively. The vaporization enthalpies have been determined using sublimation and fusion enthalpies from the literature of a series of primary amides. Also evaluated in this process were group values of 102 J*mol 1*K 1 and 47.1 kJ*mol 1 for the estimation of the heat capacity and vaporization enthalpy of a liquid primary amide (R-CONH2). The fusion enthalpies of 2-methylpropanamide, hexanamide, heptanamide, and 2-ethylpentanamide have been measured by differential scanning calorimetry (DSC) and the values compared to existing literature values where available; the following fusion enthalpies were measured (kJ*mol 1, Tfus/K): (19.9 +- 0.1, 401.6 +- 0.4); (16.8 +- 0.3, 372.4 +- 1.4); (16.2 +- 0.2, 368.6 +- 0.5); (22.5 +- 0.6, 398.2 +- 0.1), respectively. Solid solid phase transitions (kJ*mol 1, Ttrs/K) were also observed for hexanamide (5.1 +- 0.1, 306.1 +- 0.2), heptanamide (7.5 +- 0.3, 319 +- 0.8; 3.4 +- 0.1, 356.1 +- 0.2), and valpromide (1.75 +- 0.2, 360.6 +- 0.4). The crystal structure and powder pattern of heptanamide are also reported.
Compounds
# Formula Name
1 C8H17NO 2-propylpentanamide
2 C8H17NO (2S,3S)-2-ethyl-3-methylpentanamide
3 C8H17NO (2R,3S)-2-ethyl-3-methylpentanamide
4 C8H17NO (2S,3R)-2-ethyl-3-methylpentanamide
5 C8H17NO (2R,3R)-2-ethyl-3-methylpentanamide
6 C3H7NO propanamide
7 C4H9NO butanamide
8 C5H11NO pentanamide
9 C7H7NO benzamide
10 C4H9NO 2-methylpropanamide
11 C6H13NO hexanamide
12 C7H15NO heptanamide
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
  • Normal melting temperature, K ; Crystal 1
  • Crystal 1
  • Liquid
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 1
  • Triple point temperature, K ; Crystal 2
  • Crystal 2
  • Crystal 1
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 1
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal 2
  • Crystal 2
  • Crystal 1
  • Air at 1 atmosphere
  • DSC
  • 1
  • POMD
  • 1
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal 1
  • Crystal 1
  • Liquid
  • Air at 1 atmosphere
  • DSC
  • 1
  • POMD
  • 1
  • Molar enthalpy of transition or fusion, kJ/mol ; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Gas
  • Correlation gas chromatography
  • 1
  • POMD
  • 2
  • Molar enthalpy of transition or fusion, kJ/mol ; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Gas
  • Correlation gas chromatography
  • 1
  • POMD
  • 3
  • Molar enthalpy of transition or fusion, kJ/mol ; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Gas
  • Correlation gas chromatography
  • 1
  • POMD
  • 4
  • Molar enthalpy of transition or fusion, kJ/mol ; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Gas
  • Correlation gas chromatography
  • 1
  • POMD
  • 5
  • Molar enthalpy of transition or fusion, kJ/mol ; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Gas
  • Correlation gas chromatography
  • 1
  • POMD
  • 6
  • Molar enthalpy of transition or fusion, kJ/mol ; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Gas
  • Correlation gas chromatography
  • 1
  • POMD
  • 7
  • Molar enthalpy of transition or fusion, kJ/mol ; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Gas
  • Correlation gas chromatography
  • 1
  • POMD
  • 8
  • Molar enthalpy of transition or fusion, kJ/mol ; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Gas
  • Correlation gas chromatography
  • 1
  • POMD
  • 9
  • Molar enthalpy of transition or fusion, kJ/mol ; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Gas
  • Correlation gas chromatography
  • 1
  • POMD
  • 10
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 10
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DSC
  • 1
  • POMD
  • 10
  • Molar enthalpy of transition or fusion, kJ/mol ; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Gas
  • Correlation gas chromatography
  • 1
  • POMD
  • 11
  • Normal melting temperature, K ; Crystal 1
  • Crystal 1
  • Liquid
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 11
  • Triple point temperature, K ; Crystal 2
  • Crystal 2
  • Crystal 1
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 11
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal 2
  • Crystal 2
  • Crystal 1
  • Air at 1 atmosphere
  • DSC
  • 1
  • POMD
  • 11
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal 1
  • Crystal 1
  • Liquid
  • Air at 1 atmosphere
  • DSC
  • 1
  • POMD
  • 11
  • Molar enthalpy of transition or fusion, kJ/mol ; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Gas
  • Correlation gas chromatography
  • 1
  • POMD
  • 12
  • Normal melting temperature, K ; Crystal 1
  • Crystal 1
  • Liquid
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 12
  • Triple point temperature, K ; Crystal 2
  • Crystal 2
  • Crystal 1
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 12
  • Triple point temperature, K ; Crystal 3
  • Crystal 3
  • Crystal 2
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 12
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal 3
  • Crystal 3
  • Crystal 2
  • Air at 1 atmosphere
  • DSC
  • 1
  • POMD
  • 12
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal 2
  • Crystal 2
  • Crystal 1
  • Air at 1 atmosphere
  • DSC
  • 1
  • POMD
  • 12
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal 1
  • Crystal 1
  • Liquid
  • Air at 1 atmosphere
  • DSC
  • 1
  • POMD
  • 12
  • Molar enthalpy of transition or fusion, kJ/mol ; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Gas
  • Correlation gas chromatography
  • 1