Physical Properties of the 17 Isomeric Hexenes.of the API Research Series

Camin, D. L.; Rossini, Frederick D.

doi:10.1021/j150544a029

Cited by 39 publications

(29 citation statements)

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“…Usually the agreement between measurements made at Bartlesville and those of Rossini's group is within a few tenths of 1%, but not in this case. Camin and Rossini (1956) note that their sample was (99.85 ( 0.13) mol % pure. The sample used in this research was analyzed by CGC using both a polar and a nonpolar column and was shown to be >99.95 mol % pure.…”

Section: -Methylpent-1-enementioning

confidence: 95%

“…Figure 6 compares sets of vapor pressure measurements on 4-methylpent-1-ene reported in the literature (Schmitt and Boord, 1932;Boord et al, 1949;Camin and Rossini, 1956;Martire and Pollara, 1965;Vera and Prausnitz, 1971;Daubert et al, 1994) with values obtained using the Wagner equation and the parameters listed in Table 10. Agreement between the measurements is relatively poor.…”

Section: -Methylpent-1-enementioning

confidence: 99%

“…This purity difference does not seem large enough to be the source of all the discrepancy. The DIPPR Project 801 correlation equation (Daubert et al, 1994) gives heavy weight to the measurements of Camin and Rossini (1956).…”

Section: -Methylpent-1-enementioning

confidence: 99%

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Thermodynamic Properties and Ideal-Gas Enthalpies of Formation for 2-Aminoisobutyric Acid (2-Methylalanine), Acetic Acid, (Z)-5-Ethylidene-2-norbornene, Mesityl Oxide (4-Methyl-3-penten-2-one), 4-Methylpent-1-ene, 2,2‘-Bis(phenylthio)propane, and Glycidyl Phenyl Ether (1,2-Epoxy-3-phenoxypropane)

Steele¹,

Chirico²,

Cowell³

et al. 1997

J. Chem. Eng. Data

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The results of a study aimed at improvement of group-contribution methodology for estimation of thermodynamic properties of organic substances are reported. Specific weaknesses where particular group-contribution terms were unknown, or estimated because of lack of experimental data, are addressed by experimental studies of enthalpies of combustion in the condensed phase, vapor-pressure measurements, and differential scanning calorimetric (DSC) heat-capacity measurements. Ideal-gas enthalpies of formation of acetic acid, (Z)-5-ethylidene-2-norbornene, mesityl oxide (4-methyl-3-penten-2-one), 4-methylpent-1-ene, glycidyl phenyl ether (1,2-epoxy-3-phenoxypropane), and 2,2‘-bis(phenylthio)propane are reported. An enthalpy of formation of 2-aminoisobutyric acid (2-methylalanine) in the crystalline phase was determined. Using a literature value for the enthalpy of sublimation of 2-aminoisobutyric acid, a value for the ideal-gas enthalpy of formation was derived. An enthalpy of fusion was determined for 2,2‘-bis(phenylthio)propane. Two-phase (solid + vapor) or (liquid + vapor) heat capacities were determined from 300 K to the critical region or earlier decomposition temperature for all the compounds except acetic acid. For mesityl oxide and 4-methylpent-1-ene, critical temperatures and critical densities were determined from the DSC results and corresponding critical pressures derived from the fitting procedures. Group-additivity parameters and ring strain energies useful in the application of group-contribution correlations were derived.

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Section: -Methylpent-1-enementioning

confidence: 95%

Section: -Methylpent-1-enementioning

confidence: 99%

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Thermodynamic Properties and Ideal-Gas Enthalpies of Formation for 2-Aminoisobutyric Acid (2-Methylalanine), Acetic Acid, (Z)-5-Ethylidene-2-norbornene, Mesityl Oxide (4-Methyl-3-penten-2-one), 4-Methylpent-1-ene, 2,2‘-Bis(phenylthio)propane, and Glycidyl Phenyl Ether (1,2-Epoxy-3-phenoxypropane)

Steele¹,

Chirico²,

Cowell³

et al. 1997

J. Chem. Eng. Data

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“…Second, only small organic and inorganic molecules for which accurate formation enthalpies are known have been used to equilibrate the reactions (i.e., were used as A, B, and D in eq ), in particular acetylene, ethylene, ethane, CO, methane, H 2 , H 2 O, H 2 S, HCN, N 2 , and NH 3 . We expect under these conditions that the possible cancellations of errors are minimal, and better insights into the ability of the electronic structure theory methods to provide accurate reaction enthalpies can be gained. …”

Section: Computational Detailsmentioning

confidence: 99%

Heats of Formation of Medium-Sized Organic Compounds from Contemporary Electronic Structure Methods

Minenkov

Wang

et al. 2017

J. Chem. Theory Comput.

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Computational electronic structure calculations are routinely undertaken to predict thermodynamic properties of various species. However, the application of highly accurate wave function theory methods, such as the "gold standard" coupled cluster approach including single, double, and partly triple excitations in perturbative fashion, CCSD(T), to large molecules is limited due to high computational cost. In this work, the promising domain based local pair natural orbital coupled cluster approach, DLPNO-CCSD(T), has been tested to reproduce 113 accurate formation enthalpies of medium-sized molecules (few dozens heavy atoms) important for bio- and combustion chemistry via the reaction based Feller-Peterson-Dixon approach. For comparison, eight density functional theory (B3LYP, B3LYP-D3, PBE0, PBE0-D3, M06, M06-2X, ωB97X-D3, and ωB97M-V) and MP2-based (B2PLYP-D3, PWPB95-D3, B2T-PLYP, B2T-PLYP-D, B2GP-PLYP, DSD-PBEP86-D3, SCS-MP2, and OO-SCS-MP2) methods have been tested. The worst performance has been obtained for the standard hybrid DFT functionals, PBE0 (mean unsigned error (MUE)/mean signed error (MSE) = 9.1/6.0 kcal/mol) and B3LYP (MUE/MSE = 13.5/-13.3 kcal/mol). The influence of an empirical dispersion correction term on these functionals' performance is not homogeneous: B3LYP performance is improved (B3LYP-D3 (MUE/MSE = 6.0/0.8 kcal/mol)); meanwhile PBE0 performance is worse (PBE0-D3 (MUE/MSE = 14.1/13.6 kcal/mol)). The Minnesota functionals, M06 (MUE/MSE = 3.8/-2.0 kcal/mol) and M06-2X (MUE/MSE = 3.5/3.0 kcal/mol), and recently developed ωB97X-D3 (MUE/MSE = 3.2/0.2 kcal/mol) and ωB97M-V (MUE/MSE = 2.2/1.3 kcal/mol) methods provided significantly better formation enthalpies. Enthalpies of similar quality can also be obtained from some double hybrid methods (B2PLYP-D3 (MUE/MSE = 4.7/2.0 kcal/mol), PWPB95-D3 (MUE/MSE = 4.3/3.2 kcal/mol), B2T-PLYP (MUE/MSE = 4.1/-3.0 kcal/mol), and B2T-PLYP-D (MUE/MSE = 3.3/1.7 kcal/mol)). The two spin component scaled (SCS) MP2 methods resulted in even smaller errors (SCS-MP2 (MUE/MSE = 1.9/1.2 kcal/mol) and OO-SCS-MP2 (MUE/MSE = 1.6/0.1 kcal/mol)). The best performance was found for the frozen core (FC) DLPNO-CCSD(T) method with a MUE/MSE of 1.6/-1.2 kcal/mol. The performance of the DLPNO-CCSD(T) method can be further improved by running the post-SCF calculations on the B3LYP orbitals: the MUE/MSE for the DLPNO-CCSD(T,B3LYP) approximation is 1.2/-0.4 kcal/mol. We recommend the DLPNO-CCSD(T,B3LYP) method for black box applications in thermodynamics of medium-sized organic molecules when the canonical CCSD(T) calculations with basis sets of reasonable quality are prohibitively expensive.

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“…Table 3. Majer andSvoboda, 1985. b Lebedev andMiroshnichenko, 1993. c Camin and Rossini, 1956. d Lister, 1941.…”

Section: Discussion and Data Reductionmentioning

confidence: 99%

Determination of Vaporization Enthalpies of Selected Linear and Branched C₇, C₈, C₉, C₁₁, and C₁₂ Monoolefin Hydrocarbons from Transpiration and Correlation Gas-Chromatography Methods

2000

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The standard molar enthalpies of vaporization ∆ l g H°m of 1-methylcyclohexene, 4-methylcyclohexene, 2,4-dimethyl-2-pentene, cis-2-heptene, trans-4-octene, 1-nonene, 2,6-dimethylheptene, 1-undecene, trans-2,2,4,6,6-pentamethyl-3-heptene, and cis-2,2,4,6,6-pentamethyl-3-heptene at the temperature T ) 298.15 K were obtained from the temperature dependence of the vapor pressure measured by the transpiration method. The values of ∆ l g H°m(298.15 K) for these compounds and additionally for 3-methylcyclohexene were also measured using the correlation gas-chromatography method. The results from both methods are indistinguishable within the experimental uncertainties of less than (0.5 kJ‚mol -1 . Results from this work together with the data available from the literature were used to derive correlations for the prediction of the standard molar enthalpies of vaporization ∆ l g H°m(298.15 K) of monoolefins with linear and branched hydrocarbon chains.

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Physical Properties of the 17 Isomeric Hexenes.of the API Research Series

Cited by 39 publications

References 0 publications

Thermodynamic Properties and Ideal-Gas Enthalpies of Formation for 2-Aminoisobutyric Acid (2-Methylalanine), Acetic Acid, (Z)-5-Ethylidene-2-norbornene, Mesityl Oxide (4-Methyl-3-penten-2-one), 4-Methylpent-1-ene, 2,2‘-Bis(phenylthio)propane, and Glycidyl Phenyl Ether (1,2-Epoxy-3-phenoxypropane)

Thermodynamic Properties and Ideal-Gas Enthalpies of Formation for 2-Aminoisobutyric Acid (2-Methylalanine), Acetic Acid, (Z)-5-Ethylidene-2-norbornene, Mesityl Oxide (4-Methyl-3-penten-2-one), 4-Methylpent-1-ene, 2,2‘-Bis(phenylthio)propane, and Glycidyl Phenyl Ether (1,2-Epoxy-3-phenoxypropane)

Heats of Formation of Medium-Sized Organic Compounds from Contemporary Electronic Structure Methods

Determination of Vaporization Enthalpies of Selected Linear and Branched C₇, C₈, C₉, C₁₁, and C₁₂ Monoolefin Hydrocarbons from Transpiration and Correlation Gas-Chromatography Methods

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Physical Properties of the 17 Isomeric Hexenes.of the API Research Series

Cited by 39 publications

References 0 publications

Thermodynamic Properties and Ideal-Gas Enthalpies of Formation for 2-Aminoisobutyric Acid (2-Methylalanine), Acetic Acid, (Z)-5-Ethylidene-2-norbornene, Mesityl Oxide (4-Methyl-3-penten-2-one), 4-Methylpent-1-ene, 2,2‘-Bis(phenylthio)propane, and Glycidyl Phenyl Ether (1,2-Epoxy-3-phenoxypropane)

Thermodynamic Properties and Ideal-Gas Enthalpies of Formation for 2-Aminoisobutyric Acid (2-Methylalanine), Acetic Acid, (Z)-5-Ethylidene-2-norbornene, Mesityl Oxide (4-Methyl-3-penten-2-one), 4-Methylpent-1-ene, 2,2‘-Bis(phenylthio)propane, and Glycidyl Phenyl Ether (1,2-Epoxy-3-phenoxypropane)

Heats of Formation of Medium-Sized Organic Compounds from Contemporary Electronic Structure Methods

Determination of Vaporization Enthalpies of Selected Linear and Branched C7, C8, C9, C11, and C12 Monoolefin Hydrocarbons from Transpiration and Correlation Gas-Chromatography Methods

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Determination of Vaporization Enthalpies of Selected Linear and Branched C₇, C₈, C₉, C₁₁, and C₁₂ Monoolefin Hydrocarbons from Transpiration and Correlation Gas-Chromatography Methods