Thermodynamic properties of isomeric iso-butoxybenzoic acids: Experimental and theoretical study

Jakubczyk, Michał; Sporzyński, Andrzej; Emel′yanenko, Vladimir N.; Varfolomeev, Mikhail A.; Verevkin, Sergey P.

doi:10.1016/j.tca.2015.07.011

Cited by 4 publications

(7 citation statements)

References 34 publications

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“…This work complements our previous studies of the thermodynamic properties of amides and benzoic acid derivatives . We have performed experimental and computational studies of the substituted benzamides presented in Figure .…”

Section: Introductionsupporting

confidence: 52%

“…These experimental values can be used now for comparison with theoretical values calculated by any of the available high‐level quantum‐chemical methods. The high‐level composite methods have been successfully used for substituted benzamides in our recent work . A disagreement or agreement between the experimental and theoretical

Δ_{normalf} H_{m}^{\circ}

(g, 298.15 K) values could provide a criterion for the mutual validation for both results.…”

Section: Resultsmentioning

confidence: 99%

“…It is clear that the R-substituted benzamides studied in this work are ap arentt ot he familyo fR -substitutedb enzoic acids (see Figure 3) and both families are expected to exhibit comparable regularities in their thermochemical properties:t he vaporization enthalpies and the gas-phase enthalpies of formation. As am atter of fact, thesethermochemical properties for substituted benzoic acids have been evaluated just recently [5][6][7][8][9][10][11] and they have been shown to be highly internally consistent. First, we correlated the enthalpies of vaporization of pairs of similarly shaped molecules, for example, 4-nitrobenzamide and 4-nitrobenzoic acid.…”

Section: Correlation Of Vaporization Enthalpieso Fr -Substituted Benzmentioning

confidence: 99%

“…Butt oo ur surprise, av ery good linear correlation has also been observed between experimental D g l H m (298.15 K) valueso ft he R-substituted benzenes and of the 3-R-substitutedb enzamides as follows [Eq. (7)]: However,i tw as not as urprise that no correlation of vaporization enthalpies D g l H m (298.15 K) of R-benzenes and 2-R-substituted benzamides was observed, apparently owing to the specific next neighbor interactions of substituents in R-benzamides, which specifically contribute to the energetics of vaporization, and which are absentint he R-benzenes.…”

Section: Correlation Of Vaporization Enthalpies Of R-substituted Benzmentioning

confidence: 99%

“…This work complements our previouss tudies of the thermodynamic properties of amides and benzoic acid derivatives. [5][6][7][8][9][10][11][12][13] We have performed experimental and computational studies of the substituted benzamides presented in Figure 2. To perform structure-property analysis, the availablet hermochemical data for similarly structured benzamides and benzoica cidd erivatives substituted with various substituents in the ortho-, meta-, and para-positions on the benzene ring.…”

Section: Introductionmentioning

confidence: 99%

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Thermochemistry of Substituted Benzamides and Substituted Benzoic Acids: Like Tree, Like Fruit?

2018

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Structure-property analyses of thermodynamic properties in chemical families of R-substituted benzamides, R-substituted benzoic acids, as well as R-substituted benzenes have been performed. The general linear interrelations for the vaporization enthalpies and the gas-phase enthalpies of formation between the chemical families under study have been established. These linear correlations provide a simple method for prediction of thermodynamic properties for benzenes with various combination of R-group substituents on the benzene ring. In addition, the robust structure-property correlations revealed in this study can serve for the establishment of the internal consistency of experimental results available for each chemical series.

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Section: Introductionsupporting

confidence: 52%

Δ_{normalf} H_{m}^{\circ}

(g, 298.15 K) values could provide a criterion for the mutual validation for both results.…”

Section: Resultsmentioning

confidence: 99%

Section: Correlation Of Vaporization Enthalpieso Fr -Substituted Benzmentioning

confidence: 99%

Section: Correlation Of Vaporization Enthalpies Of R-substituted Benzmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Thermochemistry of Substituted Benzamides and Substituted Benzoic Acids: Like Tree, Like Fruit?

2018

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An Examination of the Phase Transition Thermodynamics of ( S )- and ( RS )-Naproxen as a Basis for the Design of Enantioselective Crystallization Processes

Buchholz

Emel′yanenko

Lorenz

et al. 2016

Journal of Pharmaceutical Sciences

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A detailed experimental analysis of the phase transition thermodynamics of (S)-naproxen and (RS)-naproxen is reported. Vapor pressures were determined experimentally via the transpiration method. Sublimation enthalpies were obtained from the vapor pressures and from independent TGA measurements. Thermodynamics of fusion which have been well-studied in the literature were systematically remeasured by DSC. Both sublimation and fusion enthalpies were adjusted to one reference temperature, T = 298 K, using measured heat capacities of the solid and the melt phase by DSC. Average values from the measurements and from literature data were suggested for the sublimation and fusion enthalpies. In order to prove consistency of the proposed values the vaporization enthalpies obtained by combination of both were compared to vaporization enthalpies obtained by the group-additivity method and the correlation-gas chromatography method. The importance of reliable and precise phase transition data for thermochemical calculations such as the prediction of solid/liquid phase behaviour of chiral compounds is highlighted.

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Phase Transition Enthalpy Measurements of Organic and Organometallic Compounds. Sublimation, Vaporization and Fusion Enthalpies From 1880 to 2015. Part 1. C₁− C₁₀

Acree

Chickos

2016

Journal of Physical and Chemical Reference Data

215

116

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Thermodynamic properties of isomeric iso-butoxybenzoic acids: Experimental and theoretical study

Cited by 4 publications

References 34 publications

Thermochemistry of Substituted Benzamides and Substituted Benzoic Acids: Like Tree, Like Fruit?

Thermochemistry of Substituted Benzamides and Substituted Benzoic Acids: Like Tree, Like Fruit?

An Examination of the Phase Transition Thermodynamics of ( S )- and ( RS )-Naproxen as a Basis for the Design of Enantioselective Crystallization Processes

Phase Transition Enthalpy Measurements of Organic and Organometallic Compounds. Sublimation, Vaporization and Fusion Enthalpies From 1880 to 2015. Part 1. C₁− C₁₀

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Thermodynamic properties of isomeric iso-butoxybenzoic acids: Experimental and theoretical study

Cited by 4 publications

References 34 publications

Thermochemistry of Substituted Benzamides and Substituted Benzoic Acids: Like Tree, Like Fruit?

Thermochemistry of Substituted Benzamides and Substituted Benzoic Acids: Like Tree, Like Fruit?

An Examination of the Phase Transition Thermodynamics of ( S )- and ( RS )-Naproxen as a Basis for the Design of Enantioselective Crystallization Processes

Phase Transition Enthalpy Measurements of Organic and Organometallic Compounds. Sublimation, Vaporization and Fusion Enthalpies From 1880 to 2015. Part 1. C1− C10

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Phase Transition Enthalpy Measurements of Organic and Organometallic Compounds. Sublimation, Vaporization and Fusion Enthalpies From 1880 to 2015. Part 1. C₁− C₁₀