Group additivity scheme for calculating the chemical thermodynamic properties of gaseous polycyclic aromatic hydrocarbons containing five-membered rings

Moiseeva, Natalia F.; Дорофеева, О. В.

doi:10.1016/0040-6031(90)80636-d

Cited by 17 publications

(16 citation statements)

References 7 publications

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“…During the past several years, substantial progress has been made extending the use of a variety of computational approaches to calculate gas-phase heat of formation values (Δ f H ° g,298 ) for C 60 (buckminsterfullerene), C 70 (C70 fullerene), corannulene, coronene, sumanene, and a variety of polycyclic aromatic hydrocarbons (PAHs). − Karton and colleagues , documented the use of very high level computational procedures (the Weizmann 1h (W1h) thermochemical protocol, double-hybrid density functional theory (DFT), second-order Møller−Plesset perturbation theory, spin-component-scaled MP2 (SCS-MP2) and G4MP2) to calculate Δ f H ° g,298 values for C60, corannulene and sumanene. The article by Karton et al was described as a tour de force by Dobek et al, who demonstrated that a set of computationally less intensive theoretical procedures could be used to calculate values consistent with those of Karton et al More recently, Chan et al .…”

Section: Introductionmentioning

confidence: 99%

Gas-Phase Heat of Formation Values for Buckminsterfullerene (C₆₀), C70 Fullerene (C₇₀), Corannulene, Coronene, Sumanene, and Other Polycyclic Aromatic Hydrocarbons Calculated Using Density Functional Theory (M06 2X) Coupled with a Versatile Inexpensive Group-Equivalent Approach

Bumpus

2018

J. Phys. Chem. A

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A straightforward procedure using density functional theory (M06 2X) coupled with a group-equivalent approach is described that was used to calculate gas-phase heat of formation (Δ H°) values for buckminsterfullerene (C), C70 fullerene (C), corannulene, coronene, and sumanene. This procedure was also used to calculate exceptionally accurate Δ H° values for a variety of single-ring aromatic and 2-7 ring polycyclic aromatic hydrocarbons (PAHs) as well as a large selection of other hydrocarbons and phenols. The approach described herein is internally consistent, and results for C, C, corannulene, coronene, and sumanene are in very close agreement with results reported by others who used higher-level computational theory. Statistical analysis of a test set containing benzene and 18 two to seven ring PAHs demonstrated that by using this approach a mean absolute deviation (MAD) and a root-mean-square deviation (RMSD) of 0.8 and 1.3 kJ/mol, respectively, were achieved for reference/experimental Δ H° values versus calculated/predicted Δ H° values. For statistical analysis of a larger test set containing 235 aromatic and aliphatic hydrocarbons and phenols, a MAD and a RMSD of 1.2 and 1.9 kJ/mol, respectively, were achieved for reference/experimental Δ H° values versus calculated/predicted Δ H° values.

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Section: Introductionmentioning

confidence: 99%

Gas-Phase Heat of Formation Values for Buckminsterfullerene (C₆₀), C70 Fullerene (C₇₀), Corannulene, Coronene, Sumanene, and Other Polycyclic Aromatic Hydrocarbons Calculated Using Density Functional Theory (M06 2X) Coupled with a Versatile Inexpensive Group-Equivalent Approach

Bumpus

2018

J. Phys. Chem. A

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“…Armitage and Bird 81 and Moiseeva and co-workers gave updated values for a few critical groups, leading to small improvements in accuracy for PAHs 82 and for compounds with five-membered rings. 83 Herndon et al 84 compared the performance of group additivity with molecular mechanics and semiempirical quantum chemistry methods on a set of 11 polycyclic benzenoid aromatic hydrocarbons to experimental values, finding that the results were generally in good agreement. Armitage and Bird 81 extended the use of group additivity to predict the stability of very large PAH species such as fullerenes (cage-like fused rings).…”

Section: Introductionmentioning

confidence: 99%

First-Principles Prediction of Enthalpies of Formation for Polycyclic Aromatic Hydrocarbons and Derivatives

Allison

Burgess

2015

J. Phys. Chem. A

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In this article, the first-principles prediction of enthalpies of formation is demonstrated for 669 polycyclic aromatic hydrocarbon (PAH) compounds and a number of related functionalized molecules. It is shown that by extrapolating density functional theory calculations to a large basis set limit and then applying a group based correction scheme that good results may be obtained. Specifically, a mean unsigned deviation and root mean squared deviation from the experimental enthalpies of formation data of 5.0 and 6.4 kJ/mol, respectively, are obtained using this scheme. This computational scheme is economical to compute and straightforward to apply, while yielding results of reasonable reliability. The results are also compared for a smaller set of molecules to the predictions given by the G3B3 and G3MP2B3 variants of the Gaussian-3 model chemistry with a mean unsigned deviation and root mean squared deviation from the experimental enthalpies of formation of 4.5 and 4.8 kJ/mol, respectively.

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“…Pyracylene 1 is a key compound in the context of aromaticity concepts and as a substructure of the fullerenes. , The published enthalpies of formation of pyracylene in the gaseous state obtained by various theoretical methods − span a range of ca. 100 kJ·mol -1 .…”

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confidence: 99%

The Enthalpy of Formation of Pyracylene

et al. 1996

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Group additivity scheme for calculating the chemical thermodynamic properties of gaseous polycyclic aromatic hydrocarbons containing five-membered rings

Cited by 17 publications

References 7 publications

Gas-Phase Heat of Formation Values for Buckminsterfullerene (C₆₀), C70 Fullerene (C₇₀), Corannulene, Coronene, Sumanene, and Other Polycyclic Aromatic Hydrocarbons Calculated Using Density Functional Theory (M06 2X) Coupled with a Versatile Inexpensive Group-Equivalent Approach

Gas-Phase Heat of Formation Values for Buckminsterfullerene (C₆₀), C70 Fullerene (C₇₀), Corannulene, Coronene, Sumanene, and Other Polycyclic Aromatic Hydrocarbons Calculated Using Density Functional Theory (M06 2X) Coupled with a Versatile Inexpensive Group-Equivalent Approach

First-Principles Prediction of Enthalpies of Formation for Polycyclic Aromatic Hydrocarbons and Derivatives

The Enthalpy of Formation of Pyracylene

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Group additivity scheme for calculating the chemical thermodynamic properties of gaseous polycyclic aromatic hydrocarbons containing five-membered rings

Cited by 17 publications

References 7 publications

Gas-Phase Heat of Formation Values for Buckminsterfullerene (C60), C70 Fullerene (C70), Corannulene, Coronene, Sumanene, and Other Polycyclic Aromatic Hydrocarbons Calculated Using Density Functional Theory (M06 2X) Coupled with a Versatile Inexpensive Group-Equivalent Approach

Gas-Phase Heat of Formation Values for Buckminsterfullerene (C60), C70 Fullerene (C70), Corannulene, Coronene, Sumanene, and Other Polycyclic Aromatic Hydrocarbons Calculated Using Density Functional Theory (M06 2X) Coupled with a Versatile Inexpensive Group-Equivalent Approach

First-Principles Prediction of Enthalpies of Formation for Polycyclic Aromatic Hydrocarbons and Derivatives

The Enthalpy of Formation of Pyracylene

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Product

Resources

About

Gas-Phase Heat of Formation Values for Buckminsterfullerene (C₆₀), C70 Fullerene (C₇₀), Corannulene, Coronene, Sumanene, and Other Polycyclic Aromatic Hydrocarbons Calculated Using Density Functional Theory (M06 2X) Coupled with a Versatile Inexpensive Group-Equivalent Approach

Gas-Phase Heat of Formation Values for Buckminsterfullerene (C₆₀), C70 Fullerene (C₇₀), Corannulene, Coronene, Sumanene, and Other Polycyclic Aromatic Hydrocarbons Calculated Using Density Functional Theory (M06 2X) Coupled with a Versatile Inexpensive Group-Equivalent Approach