Experimental and computational energetic study of 1-R-2-phenylindole (R = H, CH3, C2H5)

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

doi:10.1016/j.jct.2015.01.012

Cited by 9 publications

(2 citation statements)

References 42 publications

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“…Melting point trends in esters as a function of total number of carbons are difficult to discern from Figure 1, due to the large number of isomers. However, our review of melting data [9,22,[39][40][41][42][43][44][45][46][47][48][49][50][51][52][53][54][55][56][57] by type of ester, is more revealing (Figure 3), where A is the alkyl chain length (m in the general formula CH 3 (CH 2 ) m−1 -OC(O)-(CH 2 ) n-m−2 CH 3 ). Within a given family, such as methyl esters (A = 1), the melting point increases with the total number of carbons in the compound.…”

Section: Melting Points As a Function Of Carbons In Backbonementioning

confidence: 99%

Organic Phase Change Materials for Thermal Energy Storage: Influence of Molecular Structure on Properties

Kahwaji

White

2021

Molecules

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Materials that change phase (e.g., via melting) can store thermal energy with energy densities comparable to batteries. Phase change materials will play an increasing role in reduction of greenhouse gas emissions, by scavenging thermal energy for later use. Therefore, it is useful to have summaries of phase change properties over a wide range of materials. In the present work, we review the relationship between molecular structure and trends in relevant phase change properties (melting temperature, and gravimetric enthalpy of fusion) for about 200 organic compounds from several chemical families, namely alkanes (paraffins), fatty acids, fatty alcohols, esters, diamines, dinitriles, diols, dioic acids, and diamides. We also review availability and cost, chemical compatibility, and thermal and chemical stabilities, to provide practical information for PCM selection. Compounds with even chain alkyl lengths generally give higher melting temperatures, store more thermal energy per unit mass due to more efficient packing, and are of lower cost than the comparable compounds with odd alkyl chains.

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Section: Melting Points As a Function Of Carbons In Backbonementioning

confidence: 99%

Organic Phase Change Materials for Thermal Energy Storage: Influence of Molecular Structure on Properties

Kahwaji

White

2021

Molecules

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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.…”

Section: Introductionmentioning

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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Interplay of thermochemistry and Structural Chemistry, the journal (volume 29, 2018, issues 3–4) and the discipline

2019

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Experimental and computational energetic study of 1-R-2-phenylindole (R = H, CH3, C2H5)

Cited by 9 publications

References 42 publications

Organic Phase Change Materials for Thermal Energy Storage: Influence of Molecular Structure on Properties

Organic Phase Change Materials for Thermal Energy Storage: Influence of Molecular Structure on Properties

Energetic Effect of the Carboxylic Acid Functional Group in Indole Derivatives

Interplay of thermochemistry and Structural Chemistry, the journal (volume 29, 2018, issues 3–4) and the discipline

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