High-precision standard enthalpy of formation for polycyclic aromatic hydrocarbons predicting from general connectivity based hierarchy with discrete correction of atomization energy
1. School of Chemical Engineering, Sichuan University, Chengdu 610065, China 2. Beijing Institute of Aerospace Testing Technology, Beijing 100074, China 3. Engineering Research Center of Combustion and Cooling for Aerospace Power Ministry of Education, Chengdu 610065, China
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.
. [J]. Frontiers of Chemical Science and Engineering, 2022, 16(12): 1743-1750.
Zihan Xu, Huajie Xu, Lu Liu, Rongpei Jiang, Haisheng Ren, Xiangyuan Li. High-precision standard enthalpy of formation for polycyclic aromatic hydrocarbons predicting from general connectivity based hierarchy with discrete correction of atomization energy. Front. Chem. Sci. Eng., 2022, 16(12): 1743-1750.
X Dong, Y Chang, B Niu, M Jia. Development of a practical reaction model of polycyclic aromatic hydrocarbon (PAH) formation and oxidation for diesel surrogate fuel. Fuel, 2020, 267 : 117159 https://doi.org/10.1016/j.fuel.2020.117159
X Liu, Y Pan, P Zhang, Y Wang, G Xu, Z Su, F Yang. 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 https://doi.org/10.1007/s11705-021-2045-y
4
P Liu, Y Liu, Y Lv, W Xiong, F Hao, H Luo. Zinc modification of Ni–Ti as efficient NixZnyTi1 catalysts with both geometric and electronic improvements for hydrogenation of nitroaromatics. Frontiers of Chemical Science and Engineering, 2022, 16( 4): 461– 474 https://doi.org/10.1007/s11705-021-2072-8
5
Y Cui, Z Zeng, J Zheng, Z Huang, J Yang. 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 https://doi.org/10.1007/s11705-020-2012-z
6
J Zhang, F Tian, J Chen, Y Shi, H Cao, P Ning, Y Xie. 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 https://doi.org/10.1007/s11705-020-1932-y
7
H H Rahman, D Niemann, S H Munson-McGee. 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 https://doi.org/10.1007/s11356-021-16692-3
8
B Kärcher, F Mahrt, C Marcolli. Process-oriented analysis of aircraft soot-cirrus interactions constrains the climate impact of aviation. Communications Earth & Environment, 2021, 2( 1): 1– 9 https://doi.org/10.1038/s43247-021-00175-x
9
K O Johansson, M P Head-Gordon, P E Schrader, K R Wilson, H A Michelsen. Resonance-stabilized hydrocarbon-radical chain reactions may explain soot inception and growth. Science, 2018, 361( 6406): 997– 1000 https://doi.org/10.1126/science.aat3417
L Liu, S Chen, H Xu, Q Zhu, H Ren. Effect of alkyl substituent for cyclohexane on pyrolysis towards sooting tendency from theoretical principle. Journal of Analytical and Applied Pyrolysis, 2022, 161 : 105386 https://doi.org/10.1016/j.jaap.2021.105386
12
P P Plehiers, I Lengyel, D H West, G B Marin, C V Stevens, K M Van Geem. 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 https://doi.org/10.1016/j.cej.2021.131304
13
E Paulechka, A Kazakov. 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 https://doi.org/10.1021/acs.jpca.1c05882
14
R E Lyon. Thermal dynamics of bomb calorimeters. Review of Scientific Instruments, 2015, 86( 12): 125103 https://doi.org/10.1063/1.4936568
15
L Constantinou, R Gani. New group contribution method for estimating properties of pure compounds. AIChE Journal. American Institute of Chemical Engineers, 1994, 40( 10): 1697– 1710 https://doi.org/10.1002/aic.690401011
16
W J Hehre, R Ditchfield, L Radom, J A Pople. 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 https://doi.org/10.1021/ja00719a006
17
J W Ochterski. Thermochemistry in gaussian. Gaussian Inc, 2000, 1 : 1– 19
18
W C Herndon, P C Nowak, D A Connor, P Lin. Empirical model calculations for thermodynamic and structural properties of condensed polycyclic aromatic hydrocarbons. Journal of the American Chemical Society, 1992, 114( 1): 41– 47 https://doi.org/10.1021/ja00027a005
19
H S Wu, S I Sandler. 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 https://doi.org/10.1021/ie00053a010
20
R Sivaramakrishnan, R S Tranter, K Brezinsky. 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 https://doi.org/10.1021/jp045076m
21
G A Petersson, D K Malick, W G Wilson, J W Ochterski, J A Jr Montgomery, M Frisch. 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 https://doi.org/10.1063/1.477794
22
L A Curtiss, P C Redfern, K Raghavachari. Gaussian-4 theory. Journal of Chemical Physics, 2007, 126( 8): 084108 https://doi.org/10.1063/1.2436888
23
K Raghavachari, G W Trucks, J A Pople, M Head-Gordon. Reprint of: A fifth-order perturbation comparison of electron correlation theories. Chemical Physics Letters, 2013, 589 : 37– 40 https://doi.org/10.1016/j.cplett.2013.08.064
24
R O Ramabhadran, K Raghavachari. The successful merger of theoretical thermochemistry with fragment-based methods in quantum chemistry. Accounts of Chemical Research, 2014, 47( 12): 3596– 3604 https://doi.org/10.1021/ar500294s
25
C Dykstra, G Frenking, K Kim, G Scuseria. Theory and Applications of Computational Chemistry: The First Forty Years. Amsterdam: Elsevier, 2011, 1336
26
E Paulechka, A Kazakov. 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 https://doi.org/10.1021/acs.jpca.7b03195
27
A D Becke. Density-functional thermochemistry. III. The role of exact exchange. Journal of Chemical Physics, 1993, 98( 7): 5648– 5652 https://doi.org/10.1063/1.464913
28
Y Zhao, D G Truhlar. 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 https://doi.org/10.1007/s00214-007-0310-x
E J Prosen, R Gilmont, F D Rossini. 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 https://doi.org/10.6028/jres.034.034
32
W V Steele R D Chirico A Nguyen I A Hossenlopp N K Smith. Determination of ideal-gas enthalpies of formation for key compounds. NIPER Technical Report, 1991
33
D Bakowies. 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 https://doi.org/10.1021/acs.jctc.9b00974
34
K B Wiberg, S Hao. Enthalpies of hydration of alkenes. 4. Formation of acyclic tert-alcohols. Journal of Organic Chemistry, 1991, 56( 17): 5108– 5110 https://doi.org/10.1021/jo00017a022
35
A Molnar, R Rachford, G V Smith, R Liu. Heats of hydrogenation by a simple and rapid flow calorimetric method. Applied Catalysis, 1984, 9( 2): 219– 223 https://doi.org/10.1016/0166-9834(84)80066-4
36
J A Manion. 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 https://doi.org/10.1063/1.1420703
37
C W Gao, J W Allen, W H Green, R H West. Reaction mechanism generator: automatic construction of chemical kinetic mechanisms. Computer Physics Communications, 2016, 203 : 212– 225 https://doi.org/10.1016/j.cpc.2016.02.013
