Experimental and theoretical thermochemical studies of imidazole, imidazole-2-carboxaldehyde and 2-aminobenzimidazole

Salomón-Santiago, Carmen; Perdomo, Gastón; Flores, Henoc; Notario, Rafael; Orozco-Guareño, Eulogio

doi:10.1016/j.tca.2020.178756

Cited by 7 publications

(8 citation statements)

References 34 publications

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“…The melting temperatures ( T m ), as well as the molar enthalpies of fusion (Δ fus H m ° ) and molar entropies of fusion (Δ fus S m ° ) at T m are provided. Literature values for IM are included for comparison. ,− The DSC thermograms are provided in the Supporting Information. The samples underwent double cycles of heating and cooling.…”

Section: Resultsmentioning

confidence: 99%

The Cohesive Interactions in Phenylimidazoles

Costa,

Lobo Ferreira,

Lima

et al. 2024

J. Phys. Chem. A

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This work presents a comprehensive study exploring the thermodynamics of the solid phase of a series of phenylimidazoles, encompassing experimental measurements of heat capacity, volatility, and thermal behavior. The influence of successive phenyl group insertions on the imidazole ring on thermodynamic properties and supramolecular behavior was thoroughly examined through the evaluation of 2-phenylimidazole (2-PhI), 4-phenylimidazole (4-PhI), 4,5-diphenylimidazole (4,5-DPhI), and 2,4,5-triphenylimidazole (2,4,5-TPhI). Structural correlations between molecular structure and thermodynamic properties were established. Furthermore, the investigation employed UV−vis spectroscopy and quantum chemical calculations. Additive effects arising from the introduction of phenyl groups were found through the analysis of the solid−liquid and solid−gas equilibria, as well as heat capacities. A good correlation emerged between the thermodynamic properties of sublimation and the molar volume of the unit cell, evident across 2-PhI, 4,5-DPhI, and 2,4,5-TPhI. In contrast to its isomer 2-PhI, 4-PhI exhibited greater cohesive energy due to the stronger N−H•••N intermolecular interactions, leading to the disruption of coplanar geometry in the 4-PhI molecules. The observed higher entropies of phase transition (fusion and sublimation) are consistent with the higher structural order observed in the crystalline lattice of 4-PhI.

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Section: Resultsmentioning

confidence: 99%

The Cohesive Interactions in Phenylimidazoles

Costa,

Lobo Ferreira,

Lima

et al. 2024

J. Phys. Chem. A

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“…The molar enthalpy of sublimation at T = 298.15 K (Δ cr g H m ° ) of NSE and NSP was obtained from their molar enthalpies of vaporization (Δ l g H m ), determined following the procedure described by Ramos et al and using a TA Instruments, model Discovery, thermogravimetric analyzer. Temperature and mass calibration, verification, and details of the equipment have been described in previous works. , …”

Section: Methodsmentioning

confidence: 99%

“…The mass loss (d m /d t ) was calculated using the TA Universal Analysis software. The calculation of enthalpy of sublimation or vaporization at the average temperature is calculated using eq , as is described in previous works. , …”

Section: Methodsmentioning

confidence: 99%

“…Temperature and mass calibration, verification, and details of the equipment have been described in previous works. 49,54 The temperature intervals for analysis of NSE and NSP were T = (427−447) and (451−471) K, respectively. Masses of about 20 to 30 mg were used in each experiment, and four repetitions were made for each compound.…”

Section: Combustion Experimentsmentioning

confidence: 99%

“…The calculation of enthalpy of sublimation or vaporization at the average temperature is calculated using eq 6, as is described in previous works. 49,54…”

Section: Combustion Experimentsmentioning

confidence: 99%

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Construction and Calibration of a Semi-micro-combustion Calorimeter to Determine the Enthalpies of Combustion of N,N′-Bis(salicylidene)ethylenediamine and N,N′-Bis(salicylidene)-1,3-propanediamine

et al. 2022

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The construction and calibration of a semi-micro-combustion calorimeter for samples of around 35 mg is presented. The calorimeter energy equivalent was determined using benzoic acid as the primary standard, obtaining εcal = (2,338.81 ± 0.22) J·K–1. The operation of the calorimeter was verified by the combustion of 1,2,4-triazole and nicotinic acid as secondary and tertiary standards, respectively, obtaining results similar to data reported in the literature. The calorimeter was used to determine the massic standard energy of combustion of N,N′-bis(salicylidene)ethylenediamine and N,N′-bis(salicylidene)-1,3-propanediamine. In addition to the enthalpies of combustion, the molar standard enthalpies of formation in the crystalline phase were calculated from experimental data. Molar enthalpy of vaporization was determined by thermogravimetry and then used to obtain the molar standard enthalpies of formation in the gas phase. The melting temperatures and enthalpies of fusion of these compounds were also determined by differential scanning calorimetry.

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