The standard enthalpies of formation of 2-methylbiphenyl and diphenylmethane,

Steele, W.V.

doi:10.1006/jcht.1995.0068

Cited by 33 publications

(10 citation statements)

References 22 publications

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“…They circumvented the ambiguities of which state (solid or liquid) achieved their sample in the bomb under the pressure of oxygen at 296 or 297 K (the melting point of the diphenylmethane is within these boundaries). Their value ∆ f H°m(l) ) -( 97.1 ( 1.4) kJ‚mol -1 is substantially more reliable than earlier measurements (see the discussion by Steele et al (1995) and was taken into account here for the calculation of the standard enthalpy of formation ∆ f H°m(g) of diphenylmethane (Table 5).…”

Section: Resultsmentioning

confidence: 66%

“…The standard enthalpy of formation ∆ f H°m(l) of diphenylmethane (A) has been redeterminated by Steele et al (1995) using combustion calorimetry. They circumvented the ambiguities of which state (solid or liquid) achieved their sample in the bomb under the pressure of oxygen at 296 or 297 K (the melting point of the diphenylmethane is within these boundaries).…”

Section: Resultsmentioning

confidence: 99%

“…For the methyl substituted diphenylmethanes (Good and Lee, 1976) and some diphenylalkanes (Coops et al, 1953a,b;Serijan and Wise, 1951), values of the standard molar enthalpy of formation are reported for the condensed state. Only for diphenylmethane has ∆ f H°m(g) been measured in the gas phase (Steele et al, 1995). This limited set of thermochemical information fails to provide a reliable concept of strain for the diphenylalkanes.…”

Section: Introductionmentioning

confidence: 99%

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Thermochemical Properties of Diphenylalkanes

Verevkin

1999

J. Chem. Eng. Data

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The standard (p°) 0.1 MPa) molar enthalpies of vaporization ∆ 1 g H°m at the temperature T ) 298.15 K for diphenylmethane, (4-methylphenyl)phenylmethane, 1,1-diphenylethane, 1,1-bis(4-methylphenyl)ethane, 2-methyl-1,1-diphenylpropane, 1,1-diphenylpropane, and 1,1-diphenylbutane were obtained from the temperature dependence function of vapor pressure measured in a flow system. Standard molar enthalpies of formation ∆ f H°m(l) at the temperature T ) 298.15 K were measured using combustion calorimetry for 1,1-diphenylethane and 2-methyl-1,1-diphenylpropane. These experimental results together with the data available from the literature were used for the calculation of strain enthalpies of diphenylalkanes using the group-contribution procedure. The estimated strain enthalpies of the compounds studied were negligible within the boundaries of experimental uncertainties of about 1-2 kJ‚mol -1 . Thus no new strain corrections are needed for the prediction of the ∆ f H°m(g) of similarly shaped molecules by using groupadditivity procedures.

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Section: Resultsmentioning

confidence: 66%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Thermochemical Properties of Diphenylalkanes

Verevkin

1999

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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“…1 This work is a product of research funded by the U.S. Department of Energy Office of Fossil Energy, Advanced Oil Recovery (AOR) program. Within a portion of this research program, the thermochemical and thermophysical properties are determined for key aromatics and hydroaromatics present in the spectrum of fossil-fuel materials.…”

Section: Introductionmentioning

confidence: 99%

Thermodynamic Properties of Diphenylmethane

Chirico

Steele

2005

J. Chem. Eng. Data

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Measurements leading to the calculation of the standard thermodynamic properties for gaseous diphenylmethane (Chemical Abstracts registry number [101-81-5]) are reported. Experimental methods include adiabatic heat-capacity calorimetry, vibrating-tube densimetry, comparative ebulliometry, inclined-piston gauge manometry, and differential-scanning calorimetry (dsc). Measurement results for the enthalpy of combustion were reported previously. The critical temperature was measured with a differential scanning calorimeter. The critical pressure and critical density were estimated. Standard molar entropies, standard molar enthalpies, and standard molar Gibbs free energies of formation were derived at selected temperatures between 298.15 K and 700 K. All results are compared with experimental values reported in the literature.

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The standard enthalpies of formation of 2-methylbiphenyl and diphenylmethane,

Cited by 33 publications

References 22 publications

Thermochemical Properties of Diphenylalkanes

Thermochemical Properties of Diphenylalkanes

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

Thermodynamic Properties of Diphenylmethane

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