An Examination of the Thermodynamics of Fusion, Vaporization, and Sublimation of Ibuprofen and Naproxen by Correlation Gas Chromatography

Maxwell, R.W.; Chickos, James S.

doi:10.1002/jps.22803

Cited by 35 publications

(32 citation statements)

References 36 publications

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“…(6) Tables 5 and 6). The latter values have been in agreement (within the boundaries of experimental uncertainties) with vaporization enthalpies independently derived from the correlation gas-chromatographic method [34,42].…”

Section: Internal Consistency Of the Phase Change Enthalpies Of Benzosupporting

confidence: 50%

Benzoic acid derivatives: Evaluation of thermochemical properties with complementary experimental and computational methods

et al. 2015

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Section: Internal Consistency Of the Phase Change Enthalpies Of Benzosupporting

confidence: 50%

Benzoic acid derivatives: Evaluation of thermochemical properties with complementary experimental and computational methods

et al. 2015

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“…This result is considerably smaller than the value of 164 kJ·mol −1 previously reported by Sabbah and Minadakis . Since there is no evidence of any barrier for condensation of a gas onto a solid surface, the activation enthalpy for sublimation as measured by Gaffney et al for DL methionine should also be a good model for the sublimation enthalpy . However, differences in sublimation enthalpy between the L and the DL forms of methionine would be expected.…”

Section: Methodsmentioning

confidence: 58%

The enthalpy of formation of methionine revisited

Roux

Notario

Segura³

et al. 2012

J of Physical Organic Chem

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Methionine (2‐amino‐4‐(methylthio)butanoic acid) is a sulfur‐containing essential α‐amino acid. Despite its importance, its enthalpy of formation is contentious. From the analysis of its polymorphism confirms that the previously reported calorimetric experiments were made in the temperature interval in which a phase transitions occurs. A new value for the enthalpy of formation is suggested based on these results, as well as G4 quantum chemical calculations and thermochemical estimates. From the analysis of experimental enthalpy of formation measurements, the group increment temperature adjusted enthalpy of sublimation, quantum chemical calculations, and difference quantity derived estimates, our recommended value for the gas phase enthalpy of formation of methionine is –(430 ± 10) kJ·mol−1. Copyright © 2012 John Wiley & Sons, Ltd.

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“…Experimental data of vaporization enthalpies have essentially been extracted for this work from the large collection of W. E. Acree Jr. and J. S. Chickos [8] and J. S. Chickos et al [10][11][12][13][14], supplemented by recent data from a number of further authors publishing experimental vaporization values of several acetophenones [23], aliphatic tertiary amines [24], azidomethyl-N-nitro-oxazolidines [25], benzamides [26], benzocaine [27], bisabolol and menthol [28], crown ethers [29], N,N-dialkyl monoamides [30], fenpropidin and phencyclidine [31], flavors [32], long-chain fluorinated alcohols [33], whiskey-and methalactone [34], halogenated fluorenes [35], ibuprofen and naproxen [36], imidazo[1,2-a]pyrazine and phthalazine [37], insect pheromones [38], morpholines [39], organo(thio)phosphates [40], dialkyl phthalates [41], nitrogen heteroaromatics [42], phenylimidazoles [43], 2-acetylthiophene [44], dicarboxylic n-pentyl esters [45], and cyclic amines, ethers and alcohols [46]. The result of the atom-group parameters, resting on 3581 compounds, is summarized in Table 1.…”

Section: Enthalpy Of Vaporizationmentioning

confidence: 99%

Calculation of Five Thermodynamic Molecular Descriptors by Means of a General Computer Algorithm Based on the Group-Additivity Method: Standard Enthalpies of Vaporization, Sublimation and Solvation, and Entropy of Fusion of ordinary Organic Molecules and Total Phase-Change Entropy of Liquid Crystals

Naef

Acree

2017

Preprint

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Abstract:The calculation of the standard enthalpies of vaporization, sublimation and solvation of organic molecules is presented using a common computer algorithm on the basis of a group-additivity method. The same algorithm is also shown to enable the calculation of their entropy of fusion as well as the total phase-change entropy of liquid crystals. The present method is based on the complete break-down of the molecules into their constituting atoms and their immediate neighbourhood; the respective calculations of the contribution of the atomic groups by means of the Gauss-Seidel fitting method is based on experimental data collected from literature. The feasibility of the calculations for each of the mentioned descriptors was verified by means of a 10-fold cross-validation procedure proving the good to high quality of the predicted values for the three mentioned enthalpies and for the entropy of fusion, whereas the predictive quality for the total phase-change entropy of liquid crystals was poor. The goodness of fit (Q 2 ) and the standard deviation (σ) of the cross-validation calculations for the five descriptors was as follows: 0.9641 and 4.56 kJ/mol (N=3386 test molecules) for the enthalpy of vaporization, 0.8657 and 11.39 kJ/mol (N=1791) for the enthalpy of sublimation, 0.9546 and 4.34 kJ/mol (N=373) for the enthalpy of solvation, 0.8727 and 17.93 J/mol/K (N=2637) for the entropy of fusion and 0.5804 and 32.79 J/mol/K (N=2643) for the total phase-change entropy of liquid crystals. The large discrepancy between the results of the two closely related entropies is discussed in detail. Molecules, for which both the standard enthalpies of vaporization and sublimation were calculable, enabled the estimation of their standard enthalpy of fusion by simple subtraction of the former from the latter enthalpy. For 990 of them the experimental enthalpy-of-fusion values are also known, allowing their comparison with predictions, yielding a correlation coefficient R 2 of 0.6066.

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An Examination of the Thermodynamics of Fusion, Vaporization, and Sublimation of Ibuprofen and Naproxen by Correlation Gas Chromatography

Cited by 35 publications

References 36 publications

Benzoic acid derivatives: Evaluation of thermochemical properties with complementary experimental and computational methods

Benzoic acid derivatives: Evaluation of thermochemical properties with complementary experimental and computational methods

The enthalpy of formation of methionine revisited

Calculation of Five Thermodynamic Molecular Descriptors by Means of a General Computer Algorithm Based on the Group-Additivity Method: Standard Enthalpies of Vaporization, Sublimation and Solvation, and Entropy of Fusion of ordinary Organic Molecules and Total Phase-Change Entropy of Liquid Crystals

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