Thermodynamic properties of alkyl 1 H -indole carboxylate derivatives: A combined experimental and computational study

Carvalho, Tânia M.T.; Amaral, Luı́sa M.P.F.; Morais, Victor M.F.; Silva, Manuel A.V. Ribeiro da

doi:10.1016/j.jct.2016.01.006

Cited by 8 publications

(2 citation statements)

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“…The knowledge of the energetic properties of these compounds contributes significantly to the evaluation of their reactivity, making it important to extend the previous thermochemical studies of these compounds. − In this work, the standard ( p o = 0.1 MPa) molar enthalpies of formation at T = 298.15 K, of indole-3-carboxylic acid and 1-methylindole-3-carboxylic acid, in the crystalline phase, were derived from the standard molar energies of combustion measured by static bomb combustion calorimetry. The low volatility of indole-3-carboxylic acid prevented the determination of its enthalpy of sublimation by the Knudsen effusion technique, so, the Calvet microcalorimetry was used to measure the standard molar enthalpy of sublimation of this compound.…”

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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: Introductionmentioning

confidence: 99%

Energetic Effect of the Carboxylic Acid Functional Group in Indole Derivatives

et al. 2017

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“…Moreover, indole derivatives have many applications, in the pharmaceutical, industry in the treatment of various diseases [6]. Indole derivatives are one of the most promising heterocyclic, which have active sites in treating various diseases [7]. In addition, these compounds have broad spectrum of biological activities involving anticancer, antioxidant, antimicrobial, anticonvulsant, anti-leishmanial, antidepressants, anti-inflammatory activities and they were found to have capabilities of antiproliferative activity on cancer cells lines [8][9][10][11][12][13][14].…”

Section: Introductionmentioning

confidence: 99%