High-precision standard enthalpy of formation for polycyclic aromatic hydrocarbons predicting from general connectivity based hierarchy with discrete correction of atomization energy

Abstract

The standard enthalpy of formation is an important predictor of the reaction heat of a chemical reaction. In this work, a high-precision method was developed to calculate accurate standard enthalpies of formation for polycyclic aromatic hydrocarbons based on the general connectivity based hierarchy (CBH) with the discrete correction of atomization energy. Through a comparison with available experimental findings and other high-precision computational results, it was found that the present method can give a good description of enthalpy of formation for polycyclic aromatic hydrocarbons. Since CBH schemes can broaden the scope of application, this method can be used to investigate the energetic properties of larger polycyclic aromatic hydrocarbons to achieve a high-precision calculation at the CCSD(T)/CBS level. In addition, the energetic properties of CBH fragments can be accurately calculated and integrated into a database for future use, which will increase computational efficiency. We hope this work can give new insights into the energetic properties of larger systems.

Graphical abstract

Keywords

standard enthalpy of formation / polycyclic aromatic hydrocarbons / connectivity based hierarchy / high-precision calculation

References

[1] DongX, ChangY, NiuB, JiaM. Development of a practical reaction model of polycyclic aromatic hydrocarbon (PAH) formation and oxidation for diesel surrogate fuel. Fuel, 2020, 267 : 117159

[2] JinZ H, ChenJ T, SongS B, TianD X, TianZ Y. Pyrolysis study of a three-component surrogate jet fuel. Combustion and Flame, 2021, 226 : 190– 199

[3] LiuX, PanY, ZhangP, WangY, XuG, SuZ, YangF. Alkylation of benzene with carbon dioxide to low-carbon aromatic hydrocarbons over bifunctional Zn–Ti/HZSM-5 catalyst. Frontiers of Chemical Science and Engineering, 2022, 16( 3): 384– 396

[4] LiuP, LiuY, LvY, XiongW, HaoF, LuoH. Zinc modification of Ni–Ti as efficient Ni_xZn_yTi₁ catalysts with both geometric and electronic improvements for hydrogenation of nitroaromatics. Frontiers of Chemical Science and Engineering, 2022, 16( 4): 461– 474

[5] CuiY, ZengZ, ZhengJ, HuangZ, YangJ. Efficient photodegradation of phenol assisted by persulfate under visible light irradiation via a nitrogen-doped titanium-carbon composite. Frontiers of Chemical Science and Engineering, 2021, 15( 5): 1125– 1133

[6] ZhangJ, TianF, ChenJ, ShiY, CaoH, NingP, XieY. Conversion of phenol to cyclohexane in the aqueous phase over Ni/zeolite bi-functional catalysts. Frontiers of Chemical Science and Engineering, 2021, 15( 2): 288– 298

[7] RahmanH H, NiemannD, Munson-McGeeS H. Association among urinary polycyclic aromatic hydrocarbons and depression: a cross-sectional study from NHANES 2015–2016. Environmental Science and Pollution Research International, 2022, 29( 9): 13089– 13097

[8] KärcherB, MahrtF, MarcolliC. Process-oriented analysis of aircraft soot-cirrus interactions constrains the climate impact of aviation. Communications Earth & Environment, 2021, 2( 1): 1– 9

[9] JohanssonK O, Head-GordonM P, SchraderP E, WilsonK R, MichelsenH A. Resonance-stabilized hydrocarbon-radical chain reactions may explain soot inception and growth. Science, 2018, 361( 6406): 997– 1000

[10] ThomsonM, MitraT. A radical approach to soot formation. Science, 2018, 361( 6406): 978– 979

[11] LiuL, ChenS, XuH, ZhuQ, RenH. Effect of alkyl substituent for cyclohexane on pyrolysis towards sooting tendency from theoretical principle. Journal of Analytical and Applied Pyrolysis, 2022, 161 : 105386

[12] PlehiersP P, LengyelI, WestD H, MarinG B, StevensC V, Van GeemK M. Fast estimation of standard enthalpy of formation with chemical accuracy by artificial neural network correction of low-level-of-theory ab initio calculations. Chemical Engineering Journal, 2021, 426 : 131304

[13] PaulechkaE, KazakovA. Efficient Ab initio estimation of formation enthalpies for organic compounds: extension to sulfur and critical evaluation of experimental data. Journal of Physical Chemistry A, 2021, 125( 36): 8116– 8131

[14] LyonR E. Thermal dynamics of bomb calorimeters. Review of Scientific Instruments, 2015, 86( 12): 125103

[15] ConstantinouL, GaniR. New group contribution method for estimating properties of pure compounds. AIChE Journal. American Institute of Chemical Engineers, 1994, 40( 10): 1697– 1710

[16] HehreW J, DitchfieldR, RadomL, PopleJ A. Molecular orbital theory of the electronic structure of organic compounds. V. Molecular theory of bond separation. Journal of the American Chemical Society, 1970, 92( 16): 4796– 4801

[17] OchterskiJ W. Thermochemistry in gaussian. Gaussian Inc, 2000, 1 : 1– 19

[18] HerndonW C, NowakP C, ConnorD A, LinP. Empirical model calculations for thermodynamic and structural properties of condensed polycyclic aromatic hydrocarbons. Journal of the American Chemical Society, 1992, 114( 1): 41– 47

[19] WuH S, SandlerS I. Use of ab initio quantum mechanics calculations in group contribution methods. 1. Theory and the basis for group identifications. Industrial & Engineering Chemistry Research, 1991, 30( 5): 881– 889

[20] SivaramakrishnanR, TranterR S, BrezinskyK. Ring conserved isodesmic reactions: a new method for estimating the heats of formation of aromatics and PAHs. Journal of Physical Chemistry A, 2005, 109( 8): 1621– 1628

[21] PeterssonG A, MalickD K, WilsonW G, OchterskiJ W, MontgomeryJ A Jr, FrischM. Calibration and comparison of the Gaussian-2, complete basis set, and density functional methods for computational thermochemistry. Journal of Chemical Physics, 1998, 109( 24): 10570– 10579

[22] CurtissL A, RedfernP C, RaghavachariK. Gaussian-4 theory. Journal of Chemical Physics, 2007, 126( 8): 084108

[23] RaghavachariK, TrucksG W, PopleJ A, Head-GordonM. Reprint of: A fifth-order perturbation comparison of electron correlation theories. Chemical Physics Letters, 2013, 589 : 37– 40

[24] RamabhadranR O, RaghavachariK. The successful merger of theoretical thermochemistry with fragment-based methods in quantum chemistry. Accounts of Chemical Research, 2014, 47( 12): 3596– 3604

[25] DykstraC, FrenkingG, KimK, ScuseriaG. Theory and Applications of Computational Chemistry: The First Forty Years. Amsterdam: Elsevier, 2011, 1336

[26] PaulechkaE, KazakovA. Efficient DLPNO–CCSD(T)-based estimation of formation enthalpies for C-, H-, O-, and N-containing closed-shell compounds validated against critically evaluated experimental data. Journal of Physical Chemistry A, 2017, 121( 22): 4379– 4387

[27] BeckeA D. Density-functional thermochemistry. III. The role of exact exchange. Journal of Chemical Physics, 1993, 98( 7): 5648– 5652

[28] ZhaoY, TruhlarD G. The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals. Theoretical Chemistry Accounts, 2008, 120( 1): 215– 241

[29] TruhlarD G. Basis-set extrapolation. Chemical Physics Letters, 1998, 294( 1-3): 45– 48

[30] Gaussion09. Revision A.02. Wallingford, CT: Gaussian Inc, 2009

[31] ProsenE J, GilmontR, RossiniF D. Heats of combustion of benzene, toluene, ethylbenzene, ortho-xylene, meta-xylene, para-xylene, normal-propylbenzene, and styrene. Journal of Research of the National Bureau of Standards, 1945, 34( 1): 65– 71

[32] SteeleW V ChiricoR D NguyenA HossenloppI A SmithN K. Determination of ideal-gas enthalpies of formation for key compounds. NIPER Technical Report, 1991

[33] BakowiesD. Estimating systematic error and uncertainty in ab initio thermochemistry: II. ATOMIC(hc) enthalpies of formation for a large set of hydrocarbons. Journal of Chemical Theory and Computation, 2019, 16( 1): 399– 426

[34] WibergK B, HaoS. Enthalpies of hydration of alkenes. 4. Formation of acyclic tert-alcohols. Journal of Organic Chemistry, 1991, 56( 17): 5108– 5110

[35] MolnarA, RachfordR, SmithG V, LiuR. Heats of hydrogenation by a simple and rapid flow calorimetric method. Applied Catalysis, 1984, 9( 2): 219– 223

[36] ManionJ A. Evaluated enthalpies of formation of the stable closed shell C1 and C2 chlorinated hydrocarbons. Journal of Physical and Chemical Reference Data, 2002, 31( 1): 123– 172

[37] GaoC W, AllenJ W, GreenW H, WestR H. Reaction mechanism generator: automatic construction of chemical kinetic mechanisms. Computer Physics Communications, 2016, 203 : 212– 225

Acknowledgments

This work was supported by the National Natural Science Foundation of China (Grant Nos. 21903057 and 91841301) and National Science and Technology Major Project (Grant No. 2017-I-0004-0004).

Electronic Supplementary Material

Supplementary material is available in the online version of this article at https://dx.doi.org/10.1007/s11705-022-2184-9 and is accessible for authorized users.

RIGHTS & PERMISSIONS

2022 Higher Education Press