Thermochemical study of 2,5-dimethyl-3-furancarboxylic acid, 4,5-dimethyl-2-furaldehyde, and 3-acetyl-2,5-dimethylfuran

Silva, Manuel A.V. Ribeiro da; Amaral, Luı́sa M.P.F.

doi:10.1016/j.jct.2010.07.006

Cited by 8 publications

(3 citation statements)

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“…The results are summarized in Table . Although the vapor pressure measurement method seems to give better results than the calorimetric techniques, , several studies where both methods were used in the determination of enthalpies of sublimation demonstrate that the results obtained by the two different techniques are comparable. − …”

Section: Resultsmentioning

confidence: 99%

Energetic Effect of the Carboxylic Acid Functional Group in Indole Derivatives

et al. 2017

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The standard molar enthalpy of formation, in the gaseous phase, at T = 298.15 K, was calculated by combining, for each compound, the standard molar enthalpy of formation, in the crystalline phase, and the standard molar enthalpy of sublimation, yielding -(222.2 ± 3.5) kJ·mol and -(234.1 ± 2.1) kJ·mol for indole-3-carboxylic acid and 1-methylindole-3-carboxylic acid, respectively. Computational studies, at the G3(MP2) composite level, were conducted for indole-3-carboxylic acid and 1-methylindole-3-carboxylic acid as a complement of the experimental work, and they were also extended to the remaining isomers, indole-2-carboxylic acid, 1-methylindole-2-carboxylic acid, 3-methylindole-2-carboxylic acid, and 2-methylindole-3-carboxylic acid, to provide reliable estimates of the corresponding thermochemical parameters. The agreement of the estimates of the standard gas-phase enthalpy of formation so obtained, indole-2-carboxylic acid -(223.6 ± 0.8) kJ·mol, 1-methylindole-2-carboxylic acid -(223.7 ± 0.8) kJ·mol, 3-methylindole-2-carboxylic acid -(251.6 ± 1.0) kJ·mol, indole-3-carboxylic acid -(227.1 ± 1.1) kJ·mol, 1-methylindole-3-carboxylic acid -(238.0 ± 1.0) kJ·mol, and 2-methylindole-3-carboxylic acid -(267.2 ± 1.0) kJ·mol, with the available experimental data gives us additional confidence for the situations not studied experimentally. The enthalpic effect resulting from the entrance of the carboxyl group into the indole ring was discussed, and an enthalpic stabilization was found for indole and pyrrole derivatives when compared with other similar systems.

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Section: Resultsmentioning

confidence: 99%

Energetic Effect of the Carboxylic Acid Functional Group in Indole Derivatives

et al. 2017

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“…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]…”

Section: Sources Of Heat-of-combustion and Formation Datamentioning

confidence: 99%

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

Naef

Acree

2021

Molecules

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The calculation of the heats of combustion DH°c and formation DH°f of organic molecules at standard conditions is presented using a commonly applicable computer algorithm based on the group-additivity method. This work is a continuation and extension of an earlier publication. The method rests on the complete breakdown of the molecules into their constituting atoms, these being further characterized by their immediate neighbor atoms. The group contributions are calculated by means of a fast Gauss–Seidel fitting calculus using the experimental data of 5030 molecules from literature. The applicability of this method has been tested by a subsequent ten-fold cross-validation procedure, which confirmed the extraordinary accuracy of the prediction of DH°c with a correlation coefficient R2 and a cross-validated correlation coefficient Q2 of 1, a standard deviation σ of 18.12 kJ/mol, a cross-validated standard deviation S of 19.16 kJ/mol, and a mean absolute deviation of 0.4%. The heat of formation DH°f has been calculated from DH°c using the standard enthalpies of combustion for the elements, yielding a correlation coefficient R2 for DH°f of 0.9979 and a corresponding standard deviation σ of 18.14 kJ/mol.

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“…Despite the importance of these compounds, fundamental data on their thermodynamic properties are often scarce, hindering a detailed understanding of their energy characteristics. Continuing from previous investigations concerning furan derivatives, [ 21 , 22 , 23 , 24 ], this study aimed to fill this gap by measuring the standard ( p o = 0.1 MPa) molar enthalpies of combustion at 298.15 K for the liquids furfurylamine and 5-methylfurfurylamine, whose structures are represented in Figure 1 , using static bomb combustion calorimetry. Additionally, their standard molar enthalpies of vaporization were determined using Calvet microcalorimetry.…”

Section: Introductionmentioning

confidence: 99%

Thermochemical Research on Furfurylamine and 5-Methylfurfurylamine: Experimental and Computational Insights

Amaral,

Almeida,

Ribeiro da Silva

2024

Molecules

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The need to transition from fossil fuels to renewables arises from factors such as depletion, price fluctuations, and environmental considerations. Lignocellulosic biomass, being abundant, and quickly renewable, and not interfering with food supplies, offers a standout alternative for chemical production. This paper explores the energetic characteristics of two derivatives of furfural—a versatile chemical obtained from biomass with great potential for commercial sustainable chemical and fuel production. The standard (p° = 0.1 MPa) molar enthalpies of formation of the liquids furfurylamine and 5-methylfurfurylamine were derived from the standard molar energies of combustion, determined in oxygen and at T = 298.15 K, by static bomb combustion calorimetry. Their standard molar enthalpies of vaporization were also determined at the same temperature using high-temperature Calvet microcalorimetry. By combining these data, the gas-phase enthalpies of formation at T = 298.15 K were calculated as −(43.5 ± 1.4) kJ·mol−1 for furfurylamine, and −(81.2 ± 1.7) kJ·mol−1 for 5-methylfurfurylamine. Furthermore, a theoretical analysis using G3 level calculations was performed, comparing the calculated enthalpies of formation with the experimental values to validate both results. This method has been successfully applied to similar molecules. The discussion looks into substituent effects in terms of stability and compares them with similar compounds.

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Thermochemical study of 2,5-dimethyl-3-furancarboxylic acid, 4,5-dimethyl-2-furaldehyde, and 3-acetyl-2,5-dimethylfuran

Cited by 8 publications

References 46 publications

Energetic Effect of the Carboxylic Acid Functional Group in Indole Derivatives

Energetic Effect of the Carboxylic Acid Functional Group in Indole Derivatives

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

Thermochemical Research on Furfurylamine and 5-Methylfurfurylamine: Experimental and Computational Insights

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