Thermochemistry of drugs: experimental and theoretical study of analgesics

Nagrimanov, Ruslan N.; Зиганшин, Марат А.; Solomonov, Boris N.; Verevkin, Sergey P.

doi:10.1007/s11224-018-1188-z

Cited by 11 publications

(11 citation statements)

References 56 publications

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“…Relative differences of the experimental vapor pressures p sat from those calculated based on the fit parameters p fit for 3′-hydroxyacetanilide in a crystalline state. Solid pink ▼gas saturation (transpiration) by Perlovich et al, solid green ◆gas saturation (transpiration) by Nagrimanov et al, * and ■this work (Table ). …”

Section: Resultsmentioning

confidence: 99%

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Vapor Pressure Measurements for Acetanilide and Its Derivatives by Fast Scanning Calorimetry

et al. 2023

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The vapor pressures and enthalpies of sublimation/ vaporization/fusion were determined for acetanilide and eight of its derivatives using fast scanning calorimetry (FSC, Flash DSC 1). The vapor pressures obtained made it possible to resolve the contradictions in the literature for 4′-hydroxyacetanilide (l/cr), 3′hydroxyacetanilide (cr), and 4′-ethoxyacetanilide (l) and also confirmed the values obtained earlier for 4′-bromo-, 3′-bromo-, 4′chloro-, and 3′-chloro-acetanilides. The vapor pressures were obtained for the first time for 3′-hydroxyacetanilide in the liquid state and 4′-nitroacetanilide in the crystalline state. The sublimation and vaporization enthalpies were determined using the obtained vapor pressures. In most cases, the enthalpies coincide, within the stated uncertainties, with the weighted average values calculated from the literature data. If the deviations were larger than the uncertainties, reasonable explanations were found. The fusion enthalpies of 4′-ethoxyacetanilide, 3′hydroxyacetanilide, and 4′-hydroxyacetanilide were determined in two ways: through the fusion peak integration and by using the differences between sublimation and vaporization enthalpies. The enthalpies coincide within the error with the weighted average values calculated from the literature data.

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Section: Resultsmentioning

confidence: 99%

“…These include 4′-bromo-, 3′-bromo-, 4′-chloro-, and 3′-chloro-acetanilides. The comparison of their vapor pressures with the values obtained using the transpiration method is shown in Figures and .…”

Section: Resultsmentioning

confidence: 99%

Vapor Pressure Measurements for Acetanilide and Its Derivatives by Fast Scanning Calorimetry

et al. 2023

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“…Refs. [47][48][49][50][51][52][53][54][55][56][57][58][59][60][61] are mentioned in the Supplementary Materials.…”

Section: Supplementary Materialsmentioning

confidence: 99%

Thermodynamic Analysis of Chemical Hydrogen Storage: Energetics of Liquid Organic Hydrogen Carrier Systems Based on Methyl-Substituted Indoles

et al. 2023

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Liquid organic hydrogen carriers can store hydrogen in a safe and dense form through covalent bonds. Hydrogen uptake and release are realized by catalytic hydrogenation and dehydrogenation, respectively. Indoles have been demonstrated to be interesting candidates for this task. The enthalpy of reaction is a crucial parameter in this regard as it determines not only the heat demand for hydrogen release, but also the reaction equilibrium at given conditions. In this work, a combination of experimental measurements, quantum chemical methods and a group-additivity approach has been applied to obtain a consistent dataset on the enthalpies of formation of different methylated indole derivatives and their hydrogenated counterparts. The results show a namable influence of the number and position of methyl groups on the enthalpy of reaction. The enthalpy of reaction of the overall hydrogenation reaction varies in the range of up to 18.2 kJ·mol−1 (corresponding to 4.6 kJ·mol(H2)−1). The widest range of enthalpy of reaction data for different methyl indoles has been observed for the last step (hydrogenation for the last double bond in the five-membered ring). Here a difference of up to 7.3 kJ·mol(H2)−1 between the highest and the lowest value was found.

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“…In a series of our recent work, we have shown that the "classic" Walden constant is also valid for different families of organic compounds, such as R-acetanilides with R = alkyl, F, Cl, Br, NO 2 , NH 2 , OH, OCH 3 [49], R-substituted benzamides [50], and even for nucleobases [48]. We have found that for these series, the WC deviates from the "classic" value of 56.5 J•K −1 •mol −1 by only about ± 10 J•K −1 •mol −1 .…”

Section: Step Ii: Diagnostics Of Consistency Of Phase Transitionsmentioning

confidence: 99%

Thermochemistry in the twenty-first century–quo vadis? In silico assisted diagnostics of available thermochemical data

Verevkin

Samarov

2022

Struct Chem

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Which comes first, experiment or theory? The answer is obvious—the experiment comes first. But how to be sure that the result of the experiment is reliable? Perhaps the crucial criterion is that the result should be consistent with the network of knowledge already available. In this study, we propose a step-by-step algorithm for quality diagnostics of thermochemical data on enthalpies of formation and enthalpies of phase transitions of organic compounds. The consistency of the data is studied and established using empirical structure–property correlations as well as using quantum chemical calculations. The diagnostic algorithm is exemplarily demonstrated on a series of alkyl-substituted benzophenones for which conflicting thermochemical data were available.

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Thermochemistry of drugs: experimental and theoretical study of analgesics

Cited by 11 publications

References 56 publications

Vapor Pressure Measurements for Acetanilide and Its Derivatives by Fast Scanning Calorimetry

Vapor Pressure Measurements for Acetanilide and Its Derivatives by Fast Scanning Calorimetry

Thermodynamic Analysis of Chemical Hydrogen Storage: Energetics of Liquid Organic Hydrogen Carrier Systems Based on Methyl-Substituted Indoles

Thermochemistry in the twenty-first century–quo vadis? In silico assisted diagnostics of available thermochemical data

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