Thermochemical properties of ?-nitro derivatives of furan

Balepin, A. A.; Лебедев, В. Ф.; Кузнецова, А. А.; Venter, K. K.; Trushule, M. A.; Lolya, D. O.; Lebedev, Yu. A.

doi:10.1007/bf00961611

Cited by 6 publications

(5 citation statements)

References 2 publications

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“…However, for 3-(2-furyl)-2-propenal, the literature values [37] of the standard molar enthalpy of formation in the crystalline state À(182.0 ± 0.8) kJ Á mol À1 and the The equilibrium vapour-pressure is denoted by p, and the deviations of experimental results from those given by the Clausius-Clapeyron equation are denoted by Dln(p/Pa). For the studied vinyl furans, the standard molar enthalpies of formation in the gaseous state, at T = 298.15 K, obtained by the addition of the derived standard molar enthalpies of formation in the crystalline or liquid state and the standard molar enthalpies of sublimation/vaporization, are summarized in table 9.…”

Section: Resultsmentioning

confidence: 99%

Standard molar enthalpies of formation of some vinylfuran derivatives

Silva

Amaral

2009

The Journal of Chemical Thermodynamics

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Section: Resultsmentioning

confidence: 99%

Standard molar enthalpies of formation of some vinylfuran derivatives

Silva

Amaral

2009

The Journal of Chemical Thermodynamics

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“…Moreover, thermochemical studies of the enthalpies of formation of 5-nitro-2-acetoxy-2,5-dihydro-2-furancarboxylic acid methyl ester and 5-nitro-2-acetoxy-2,5-dihydrofurfural diacetate have been reported [12] but these species are too functionalized, too cluttered, to be of relevance here, especially since the data is only for the solid phase. Finally, we note that the gas phase enthalpies of formation of phthalan [13a] and 2,3-dihydrobenzofuran [13b], the benzo analogs of species 1 and 2, respectively, have been reported to be −30.1 ± 1.0 and − 46.5 ± 0.8 kJ mol −1 , resulting in a difference of 16.4 ± 1.3 kJ mol −1 favoring the conjugated isomer.…”

Section: Methodsmentioning

confidence: 97%

Relative thermodynamic stabilities of the isomeric dihydrofurans and isomeric dihydropyrans. An experimental and DFT study

2006

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The relative thermodynamic stabilities of 2,5-dihydrofuran (1) and 2,3-dihydrofuran (2), and of 3,4-dihydro-6H-pyran (3) and 3,4-dihydro-2H-pyran (4), were determined at several temperatures by base-catalyzed equilibration in DMSO solution.The second-law reaction enthalpy agrees with literature data based on calorimetric enthalpies of hydrogenation of the isomeric forms in hexane. For 3 → 4, G • m = -19.3 ± 0.2 kJ mol −1 , H • m = -18.9 ± 1.1 kJ mol −1 and S • m = 1.1 ± 3.0 J K −1 mol −1 at 298.15 K: the experimental reaction enthalpy is in marked disagreement with literature data based on estimation. On the other hand, both of the experimental reaction enthalpies of the present study are in good agreement with DFT calculations using the B3LYP functional and 6-311 + G(2d,p) basis set.

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“…The results are in good agreement with density functional theory atomization calculations by Li et al75 with B3LYP, B3PW91, and MPW1PW91 all predicting ca. −37.5, but PBEPBE is the exception at −45 kJ mol −1 ; the experimental value76 is considerably higher at −29 ± 3 kJ mol −1 .Both aniline and N-methyl aniline can be derived from the set of working reactions:…”

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confidence: 99%

A Database of Formation Enthalpies of Nitrogen Species by Compound Methods (CBS-QB3, CBS-APNO, G3, G4)

Simmie

2015

J. Phys. Chem. A

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Accurate thermochemical data for compounds containing C/H/N/O are required to underpin kinetics simulation and modeling of the reactions of these species in different environments. There is a dearth of experimental data so computational quantum chemistry has stepped in to fill this breach and to verify whether particular experiments are in need of revision. A number of composite model chemistries (CBS-QB3, CBS-APNO, G3, and G4) are used to compute theoretical atomization energies and hence enthalpies of formation at 0 and 298.15 K, and these are benchmarked against the best available compendium of values, the Active Thermochemical Tables or ATcT. In general the agreement is very good for some 28 species with the only discrepancy being for hydrazine. It is shown that, although individually the methods do not perform that well, collectively the mean unsigned error is <1.7 kJ mol(-1); hence, this approach provides a useful tool to screen published values and validate new experimental results. Using multiple model chemistries does have some drawbacks but can produce good results even for challenging molecules like HOON and CN2O2. The results for these smaller validated molecules are then used as anchors for determining the formation enthalpies of larger species such as methylated hydrazines and diazenes, five- and six-membered heterocyclics via carefully chosen isodesmic working reactions with the aim of resolving some discrepancies in the literature and establishing a properly validated database. This expanded database could be useful in testing the performance of computationally less-demanding density function methods with newer functionals that have the capacity to treat much larger systems than those tested here.

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Thermochemical properties of ?-nitro derivatives of furan

Cited by 6 publications

References 2 publications

Standard molar enthalpies of formation of some vinylfuran derivatives

Standard molar enthalpies of formation of some vinylfuran derivatives

Relative thermodynamic stabilities of the isomeric dihydrofurans and isomeric dihydropyrans. An experimental and DFT study

A Database of Formation Enthalpies of Nitrogen Species by Compound Methods (CBS-QB3, CBS-APNO, G3, G4)

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