Combustion chemistry via metadynamics: Benzyl decomposition revisited

Journal of Physical Chemistry A

Volumn 119, Issue 6, 2015, Pages 978-989

  Polino, Daniela ^a   Parrinello, Michele ^a  

^a UNIVERSITY OF LUGANO   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC HYDROCARBONS; COMBUSTION; DECOMPOSITION; FREE ENERGY; MOLECULAR DYNAMICS; REACTION INTERMEDIATES; REACTION KINETICS;

AB INITIO MOLECULAR DYNAMICS; BENZYL RADICALS; CHEMICAL EVOLUTION; COMBUSTION CHEMISTRY; COMBUSTION PRO-CESS; DECOMPOSITION PATHWAY; ENERGY EVALUATION; POLYCYCLIC AROMATIC HYDROCARBONS (PAHS);

POLYCYCLIC AROMATIC HYDROCARBONS;

EID: 84922775046     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp5118807     Document Type: Article

References (70)

1. Richter, H.; Howard, J. B. Formation of Polycyclic Aromatic Hydrocarbons and their Growth to Soot-a Review of Chemical Reaction Pathways Prog. Energy Combust. 2000, 26, 565-608
2. Frenklach, M. Reaction Mechanism of Soot Formation in Flames Phys. Chem. Chem. Phys. 2002, 4, 2028-2037
3. Slavinskaya, N. A.; Frank, P. A Modelling Study of Aromatic Soot Precursors Formation in Laminar Methane and Ethene Flames Combust. Flame 2009, 156, 1705-1722
4. Marinov, N. M.; Pitz, W. J.; Westbrook, C. K.; Castaldi, M. J.; Senkan, S. M. Modeling of Aromatic and Polycyclic Aromatic Hydrocarbon Formation in Premixed Methane and Ethane Flames Combust. Sci. Technol. 1996, 116-117, 211-287
5. Marinov, N. M.; Castaldi, M. J.; Melius, C. F.; Tsang, W. Aromatic and Polycyclic Aromatic Hydrocarbon Formation in a Premixed Propane Flame Combust. Sci. Technol. 1997, 128, 295-342
6. Miller, J. A.; Melius, C. F. Kinetic and Thermodynamic Issues in the Formation of Aromatic-Compounds in Flames of Aliphatic Fuels Combust. Flame 1992, 91, 21-39
7. Miller, J. A.; Pilling, M. J.; Troe, J. Unravelling Combustion Mechanisms through a Quantitative Understanding of Elementary Reactions Proc. Combust. Inst. 2005, 30, 43-88
8. Hansen, N.; Miller, J. A.; Klippenstein, S. J.; Westmoreland, P. R.; Kohse-Höinghaus, K. Exploring Formation Pathways of Aromatic Compounds in Laboratory-Based Model Flames of Aliphatic Fuels Combust Explos. Shock Waves 2012, 48, 508-515
9. Marinov, N. M.; Pitz, W. J.; Westbrook, C. K.; Vincitore, A. M.; Castaldi, M. J.; Senkan, S. M.; Melius, C. F. Aromatic and Polycyclic Aromatic Hydrocarbon Formation in a Laminar Premixed n-Butane Flame Combust. Flame 1998, 114, 192-213
10. 6 Potential J. Phys. Chem. A 2003, 107, 7783-7799
11. Miller, J. A.; Klippenstein, S. J. The Recombination of Propargyl Radicals: Solving the Master Equation J. Phys. Chem. A 2001, 105, 7254-7266
12. Miller, J. A.; Klippenstein, S. J.; Georgievskii, Y.; Harding, L. B.; Allen, W. D.; Simmonett, A. C. Reactions between Resonance-Stabilized Radicals: Propargyl + Allyl J. Phys. Chem. A 2010, 114, 4881-4890
13. Matsugi, A.; Suma, K.; Miyoshi, A. Kinetics and Mechanisms of the Allyl + Allyl and Allyl + Propargyl Recombination Reactions J. Phys. Chem. A 2011, 115, 7610-7624
14. Matsugi, A.; Miyoshi, A. Computational Study on the Recombination Reaction Between Benzyl and Propargyl Radicals Int. J. Chem. Kinet. 2012, 44, 206-218
15. 5 Cyclopentadienyl Moiety Proc. Combust. Inst. 1996, 26, 685-692
16. Mebel, A. M.; Kislov, V. V. Can the C(5)H(5) + C(5)H(5) -> C(10)H(10) -> C(10)H(9) + H/C(10)H(8) + H(2) Reaction Produce Naphthalene? An Ab Initio/RRKM Study J. Phys. Chem. A 2009, 113, 9825-9833
17. 5 Reaction Proc. Combust. Inst. 2013, 34, 557-564
18. Kislov, V. V.; Mebel, A. M. An Ab Initio G3-type/Statistical Theory Study of the Formation of Indene in Combustion Flames. II. The Pathways Originating from Reactions of Cyclic C-5 Species-Cyclopentadiene and Cyclopentadienyl radicals J. Phys. Chem. A 2008, 112, 700-716
19. Wang, D.; Violi, A.; Kim, D. H.; Mullholland, J. A. Formation of Naphthalene, Indene, and Benzene from Cyclopentadiene Pyrolysis: A DFT Study J. Phys. Chem. A 2006, 110, 4719-4725
20. Cavallotti, C.; Polino, D.; Frassoldati, A.; Ranzi, E. Analysis of Some Reaction Pathways Active during Cyclopentadiene Pyrolysis J. Phys. Chem. A 2012, 116, 3313-3324
21. Klippenstein, S. J.; Pande, V. S.; Truhlar, D. G. Chemical Kinetics and Mechanisms of Complex Systems: A Perspective on Recent Theoretical Advances J. Am. Chem. Soc. 2013, 136, 528-546
22. Karton, A.; Rabinovich, E.; Martin, J. M. L.; Ruscic, B. W4 Theory for Computational Thermochemistry: In Pursuit of Confident sub-kJ/mol Predictions. J. Chem. Phys. 2006, 125.
23. Harding, M. E.; Vazquez, J.; Ruscic, B.; Wilson, A. K.; Gauss, J.; Stanton, J. F. High-accuracy Extrapolated Ab Initio Thermochemistry. III. Additional Improvements and Overview. J. Chem. Phys. 2008, 128.
24. Barducci, A.; Bonomi, M.; Parrinello, M. Metadynamics WIREs Comput. Mol. Sci. 2011, 1, 826-843
25. Rao, V. S.; Skinner, G. B. Formation of Hydrogen Atoms in Pyrolysis of Ethylbenzene behind Shock Waves. Rate Constants for the Thermal Dissociation of the Benzyl Radical Proc. Combust. Inst. 1986, 21, 809
26. Braun-Unkhoff, M.; Frank, P.; Just, T. High-Temperature Reactions of Benzyl Radicals Ber. Bunsen-Ges. Phys. Chem. 1990, 94, 1417-1425
27. Hippler, H.; Reihs, C.; Troe, J. Elementary Steps in the Pyrolysis of Toluene and Benzyl Radicals Z. Phys. Chem. (Muenchen, Ger.) 1990, 167, 1-16
28. 6 J. Photochem. Photobiol., A 1994, 80, 33
29. Oehlschlaeger, M. A.; Davidson, D. F.; Hanson, R. K. High-Temperature Thermal Decomposition of Benzyl Radicals J. Phys. Chem. A 2006, 110, 6649-6653
30. Sivaramakrishnan, R.; Tranter, R. S.; Brezinsky, K. High Pressure Pyrolysis of Toluene. 2. Modeling Benzyl Decomposition and Formation of Soot Precursors J. Phys. Chem. A 2006, 110, 9400-9404
31. 2Br: Implications for High Temperature Benzyl Decomposition Proc. Combust. Inst. 2011, 33, 243-250
32. Jones, J.; Bacskay, G. B.; Mackie, J. C. Decomposition of the Benzyl Radical: Quantum Chemical and Experimental (Shock Tube) Investigations of Reaction Pathways J. Phys. Chem. A 1997, 101, 7105-7113
33. Cavallotti, C.; Derudi, M.; Rota, R. On the Mechanism of Decomposition of the Benzyl Radical Proc. Combust. Inst. 2009, 32, 115-121
34. 6) + H J. Phys. Chem. A 2009, 113, 6111-6120
35. Derudi, M.; Polino, D.; Cavallotti, C. Toluene and Benzyl Decomposition Mechanisms: Elementary Reactions and Kinetic Simulations Phys. Chem. Chem. Phys. 2011, 13, 21308-21318
36. Smith, R. D. A Direct Mass Spectrometric Study of the Mechanism of Toluene Pyrolysis at High Temperatures J. Phys. Chem. 1979, 83, 1553-1563
37. 6 Pathway in a Rich Toluene Flame J. Phys. Chem. A 2009, 113, 10913-10922
38. Lemieux, J. M. Thermal Decomposition of Molecules Relevant to Combustion and Chemical Vapor Deposition by Flash Pyrolysis Time-of-Flight Mass Spectrometry 2013.
39. CP2K website. http://www.cp2k.org.
40. VandeVondele, J.; Krack, M.; Mohamed, F.; Parrinello, M.; Chassaing, T.; Hutter, J. Quickstep: Fast and Accurate Density Functional Calculations Using a Mixed Gaussian and Plane Waves Approach Comput. Phys. Commun. 2005, 167, 103-128
41. VandeVondele, J.; Hutter, J. Gaussian Basis Sets for Accurate Calculations on Molecular Systems in Gas and Condensed Phases J. Chem. Phys. 2007, 127, 114105
42. Goedecker, S.; Teter, M.; Hutter, J. Separable Dual-Space Gaussian Pseudopotentials Phys. Rev. B: Condens. Matter 1996, 54, 1703-1710
43. Hartwigsen, C.; Goedecker, S.; Hutter, J. Relativistic Separable Dual-Space Gaussian Pseudopotentials from H to Rn Phys. Rev. B: Condens. Matter 1998, 58, 3641-3662
44. Becke, A. D. Density-Functional Thermochemistry. III. The Role of Exact Exchange J. Chem. Phys. 1993, 98, 5648-5652
45. Lee, C.; Yang, W.; Parr, R. G. Development of the Colle-Salvetti Correlation-Energy Formula into a Functional of the Electron Density Phys. Rev. B 1988, 37, 785
46. Martyna, G. J.; Tuckerman, M. E. A Reciprocal Space Based Method for Treating Long Range Interactions in Ab Initio and Force-Field-Based Calculations in Clusters J. Chem. Phys. 1999, 110, 2810-2821
47. Bussi, G.; Donadio, D.; Parrinello, M. Canonical Sampling through Velocity Rescaling J. Chem. Phys. 2007, 126, 014101
48. Barducci, A.; Bussi, G.; Parrinello, M. Well-Tempered Metadynamics: A Smoothly Converging and Tunable Free-Energy Method Phys. Rev. Lett. 2008, 100, 020603
49. Pietrucci, F.; Andreoni, W. Graph Theory Meets Ab Initio Molecular Dynamics: Atomic Structures and Transformations at the Nanoscale Phys. Rev. Lett. 2011, 107, 085504
50. Zheng, S. H.; Pfaendtner, J. Car-Parrinello Molecular Dynamics plus Metadynamics Study of High-Temperature Methanol Oxidation Reactions Using Generic Collective Variables J. Phys. Chem. C 2014, 118, 10764-10770
51. Downs, G. M.; Gillet, V. J.; Holliday, J. D.; Lynch, M. F. Review of Ring Perception Algorithms for Chemical Graphs J. Chem. Inf. Comput. Sci. 1989, 29, 172-187
52. Hanser, T.; Jauffret, P.; Kaufmann, G. A New Algorithm for Exhaustive Ring Perception in a Molecular Graph J. Chem. Inf. Comput. Sci. 1996, 36, 1146-1152
53. Kolodzik, A.; Urbaczek, S.; Rarey, M. Unique Ring Families: A Chemically Meaningful Description of Molecular Ring Topologies J. Chem. Inf. Model. 2012, 52, 2013-2021
54. Bonomi, M.; Branduardi, D.; Bussi, G.; Camilloni, C.; Provasi, D.; Raiteri, P.; Donadio, D.; Marinelli, F.; Pietrucci, F.; Broglia, R. A. PLUMED: A Portable Plugin for Free-Energy Calculations with Molecular Dynamics Comput. Phys. Commun. 2009, 180, 1961-1972
55. Tribello, G. A.; Bonomi, M.; Branduardi, D.; Camilloni, C.; Bussi, G. PLUMED 2: New Feathers for an Old Bird Comput. Phys. Commun. 2014, 185, 604-613
56. Staroverov, V. N.; Scuseria, G. E.; Tao, J.; Perdew, J. P. Comparative Assessment of a New Nonempirical Density Functional: Molecules and Hydrogen-Bonded Complexes J. Chem. Phys. 2003, 119, 12129-12137
57. Ditchfield, R.; Hehre, W. J.; Pople, J. A. Self-Consistent Molecular Orbital Methods. 9. Extended Gaussian-type Basis for Molecular-Orbital Studies of Organic Molecules J. Chem. Phys. 1971, 54, 724-728
58. Peng, C. Y.; Ayala, P. Y.; Schlegel, H. B.; Frisch, M. J. Using Redundant Internal Coordinates to Optimize Equilibrium Geometries and Transition States J. Comput. Chem. 1996, 17, 49-56
59. Raghavachari, K.; Trucks, G. W.; Pople, J. A.; Headgordon, M. A 5th-order Perturbation Comparison of Electron Correlation Theories Chem. Phys. Lett. 1989, 157, 479-483
60. Woon, D. E.; Dunning, T. H. Gaussian-Basis Sets for use in Correlated Molecular Calculations 0.5. Core-Valence Basis-Sets for Boron through Neon J. Chem. Phys. 1995, 103, 4572-4585
61. Martin, J. M. L. Ab Initio Total Atomization Energies of Small Molecules-Towards the Basis Set Limit Chem. Phys. Lett. 1996, 259, 669-678
62. Fascella, S.; Cavallotti, C.; Rota, R.; Carra, S. Quantum Chemistry Investigation of Key Reactions Involved in the Formation of Naphthalene and Indene J. Phys. Chem. A 2004, 108, 3829-3843
63. Frisch, M. J.; Gaussian 09, revision A.02; Gaussian, Inc.: Wallingford, CT, 2009.
64. Glasstone, S.; Laidler, K. J.; Eyring, H. The Theory of Rate processes: the Kinetics of Chemical Reactions, Viscosity, Diffusion and Electrochemical Phenomena. McGraw-Hill Book Company, Inc.: New York, 1941.
65. Truhlar, D. G.; Garrett, B. C. Variational Transition-State Theory Acc. Chem. Res. 1980, 13, 440-448
66. 5 Fulvenallenyl Radical as a Combustion Intermediate: Potential New Pathways to Two- and Three-Ring PAHS J. Phys. Chem. A 2009, 113, 12045-12048
67. Fascella, S.; Cavallotti, C.; Rota, R.; Carra, S. The Peculiar Kinetics of the Reaction between Acetylene and the Cyclopentadienyl Radical J. Phys. Chem. A 2005, 109, 7546-7557
68. Vansteenkiste, P.; Van Speybroeck, V.; Marin, G. B.; Waroquier, M. Ab Initio Calculation of Entropy and Heat Capacity of Gas-Phase n-Alkanes Using Internal Rotations J. Phys. Chem. A 2003, 107, 3139-3145
69. Van Speybroeck, V.; Van Neck, D.; Waroquier, M. Ab Initio Study of Radical Reactions: Role of Coupled Internal Rotations on the Reaction Kinetics (III) J. Phys. Chem. A 2002, 106, 8945-8950
70. Tiwary, P.; Parrinello, M. A Time-Independent Free Energy Estimator for Metadynamics. J. Phys. Chem. B 2014.