Thermodynamic properties of some isomeric 5-(nitrophenyl)-furyl-2 derivatives

Abstract

Background The aim of the current work was to determine thermodynamical properties of 5-(nitrophenyl)-2-furaldehyde oximes and 3-[5-(nitrolphenyl)-2-furyl]acrylic acids. Results The temperature dependences of saturated vapor pressures of 5-(nitrophenyl)-2-furaldehyde oximes and 3-[5-(nitrolphenyl)-2-furyl]acrylic acids were determined by the Knudsen effusion method. The results are presented by the Clapeyron–Clausius equation in linear form, and via this form, the standard enthalpies of sublimation of compounds were calculated at 298.15 K. The standard molar formation enthalpies of compounds in crystalline state at 298.15 K were determined indirectly from the corresponding standard molar combustion enthalpy, obtained using combustion bomb calorimetry. The non-nearest neighbour interactions (strain) in molecule were defined. The ideal-gas enthalpies of investigated compounds formation and the data available from the literature were used for calculation of group-additivity parameters and the correction terms useful in the application of the Benson correlation. Conclusion Determining the thermodynamic properties for these compounds will contribute to solving practical problems pertaining to optimization processes of their synthesis, purification and application. It will also provide a more thorough insight regarding the theoretical knowledge of their nature and are necessary for the application of the Benson group-contribution correlation for calculation of (g) calc. Electronic supplementary material The online version of this article (10.1186/s13065-019-0619-2) contains supplementary material, which is available to authorized users.

Thermochemistry of Furan and Its Derivatives: A High-Level Ab Initio Study

“…Particular attention should be paid to compounds 20 , 27 , 28 , 31 , and 34 – 39 , for which the discrepancies with calculated values range from 29 to 72 kJ·mol –1 . Experimental data of these compounds were obtained in the same research group, ,,, and the results may contain the systematic errors. For only one compound, 2-furanacrylic acid ( 20 ), experimental measurements were also carried out in other work by Ribeiro da Silva and Amaral .…”

“…Among the reasons for possible errors in the results ,, for compounds 27 , 28 , 31 , and 34 – 39 , note that no control for absence of nitrogen oxides (NO and NO 2 ) was carried out when analyzing the gas combustion products, and therefore, the correction for nitric acid formation was most likely determined inaccurately. In addition, the purity of the substances was not fully confirmed.…”

Enthalpy of Formation and Combustion of 5-(4-Nitrophenyl)furan-2-Carbaldehyde and Its 2-Methyl and 2-Oxomethyl Derivatives in the Condensed State

“…The presented work is a continuation of thermodynamic studies of arylfuran derivatives, the results of which were published in [21][22][23].…”

Revision and Extension of a Generally Applicable Group-Additivity Method for the Calculation of the Standard Heat of Combustion and Formation of Organic Molecules

“…A considerable number of experimental combustion and formation data have been published for heterocyclic compounds, including hetarenes, unsubstituted and substituted by functional groups just mentioned. According to the hetero elements in the ring system, they have been subdivided into N x -heterocycles (where x is 1 to 4) , N,O-heterocycles [424][425][426][427][428][429][430][431][432][433], N,S-heterocycles [434][435][436][437][438], O x -heterocycles [439][440][441][442][443][444][445][446][447][448][449][450][451][452], and S x -heterocycles [280,[282][283][284][453][454][455][456][457][458][459][460][461]. A small number of papers contributed data for hetarenes with several element combinations [462][463][464]…”