A quantum monte carlo study of the reactions of CH with acrolein

Journal of Physical Chemistry A

Volumn 119, Issue 18, 2015, Pages 4214-4223

  Pakhira, Srimanta ^a,b   Lengeling, Benjamin S ^a,b,d   Olatunji Ojo, Olayinka ^c   Caffarel, Michel ^d   Frenklach, Michael ^a,e   Lester, William A ^a,b  

^a LAWRENCE BERKELEY NATIONAL LABORATORY   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c UNIVERSITY OF CALIFORNIA   (United States)

^d UNIVERSITÉ DE TOULOUSE   (France)

^e UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; HERBICIDES; WAVE FUNCTIONS;

ATOMIZATION ENERGIES; COMBUSTION PRO-CESS; DIFFUSION MONTE CARLO; EQUILIBRIUM GEOMETRIES; QUANTUM MONTE CARLO; QUANTUM MONTE CARLO STUDIES; REACTION BARRIERS; THEORETICAL STUDY;

MONTE CARLO METHODS;

ACROLEIN; ALKENE;

CHEMISTRY; MONTE CARLO METHOD; QUANTUM THEORY; THERMODYNAMICS;

ACROLEIN; ALKENES; MONTE CARLO METHOD; QUANTUM THEORY; THERMODYNAMICS;

EID: 84928957972     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/acs.jpca.5b00919     Document Type: Article

References (88)

1. Grosjean, D. Atmospheric Chemistry of Toxic Contaminants. 3. Unsaturated Aliphatics: Acrolein, Acrylonitrile, Maleic Anhydride J. Air Waste Manage. Assoc. 1990, 40, 1664-1668
2. Berndt, T.; Böge, O. Atmospheric Reaction of OH Radicals with 1,3-Butadiene and 4-Hydroxy-2-butenal J. Phys. Chem. A 2007, 111, 12099-12105
3. Liu, X.; Jefries, H. E.; Sexton, K. G. Hydroxyl Radical and Ozone Initiated Photochemical Reactions of 1,3-Butadiene Atmos. Environ. 1999, 33, 3005-3022
4. Tuazon, E. C.; Alvarado, A.; Aschmann, S. M.; Atkinson, R.; Arey, J. Products of the Gas-Phase Reactions of 1,3-Butadiene with OH and NO3 Radicals Environ. Sci. Technol. 1999, 33, 3586-3595
5. Tanimoto, H.; Akimoto, H. A New Peroxycarboxylic Nitric Anhydride Identified in the Atmosphere: CH2=CHC(O)OONO2 (APAN) Geophys. Res. Lett. 2001, 28, 2831-2834
6. Roberts, J. M.; Flocke, F.; Weinheimer, A.; Tanimoto, H.; Jobson, B. T.; Riemer, D.; Apel, E.; Atlas, E.; Donnelly, S.; Stroud, V.; Johnston, K.; Weaver, R.; Fehsenfeld, F. C. Observations of APAN during TexAQS 2000 Geophys. Res. Lett. 2001, 28, 4195-4198
7. Arntz, D.; Fischer, A.; Höpp, M.; Jacobi, S.; Sauer, J.; Ohara, T.; Sato, T.; Shimizu, N.; Schwind, H. Acrolein and Methacrolein. Ullmann's Encyclopedia of Industrial Chemistry; Wiley-VCH: Weinheim, 2012.
8. Bein, K.; Leikauf, G. D. Acrolein-A Pulmonary Hazard Mol. Nutr. Food Res. 2011, 55, 1342-1360
9. Song, C. L.; Zhao, Z. A.; Lv, G.; Song, J. N.; Liu, L. D.; Zhao, R. F. Carbonyl Compound Emissions from a Heavy-duty Diesel Engine Fueled with Diesel Fuel and Ethanol-diesel Blend Chemosphere 2010, 79, 1033-1039
10. Esterbauer, H.; Schaur, R. J.; Zollner, H. Chemistry and Biochemistry of 4-Hydroxynonenal, Malonaldehyde and Related Aldehydes Free Radical Biol. Med. 1991, 11, 81-128
11. Stevens, J. F.; Maier, C. S. Acrolein: Sources, Metabolism, and Biomolecular Interactions Relevant to Human Health and Disease Mol. Nutr. Food Res. 2008, 52, 7-25
12. Spada, N.; Fujii, E.; Cahill, T. M. Diurnal Cycles of Acrolein and Other Small Aldehydes in Regions Impacted by Vehicle Emissions Environ. Sci. Technol. 2008, 42, 7084-7090
13. Woodruff, T. J.; Caldwell, J.; Cogliano, V. J.; Axelrad, D. A. Estimating Cancer Risk from Outdoor Concentrations of Hazardous Air Pollutants in 1990 Environ. Res. 2000, 82, 194-206
14. Kohse-Hoinghaus, K.; Osswald, P.; Cool, T. A.; Kasper, T.; Hansen, N.; Qi, F.; Westbrook, C. K.; Westmoreland, P. R. Biofuel Combustion Chemistry: From Ethanol to Biodiesel Angew. Chem., Int. Ed. 2010, 49, 3572-3597
15. Amin, M. Y.; EI-Nawawy, M. S. The Chemical Evaluation in a Model of Contracting Cloud Earth, Moon, Planets 1996, 75, 25-39
16. Brownsword, R. A.; Sims, I. R.; Smith, I. W. M.; Stewart, D. W. A.; Canosa, A.; Rowe, B. R. The Radiative Association of CH with H2: A Mechanism for Formation of CH3 in Interstellar Clouds Astrophys. J. 1997, 485, 195-202
17. Miller, J. A.; Bowman, C. T. Mechanism and Modeling of Nitrogen Chemistry in Combustion Prog. Energy Combust. Sci. 1989, 15, 287-338
18. Miller, J. A.; Kee, R. J.; Westbrook, C. Chemical Kinetics and Combustion Modeling Annu. Rev. Phys. Chem. 1990, 41, 345-387
19. Canosa, A.; Sims, I. R.; Travers, D.; Smith, I. W. M.; Rowe, B. R. Reactions of the Methylidine Radical with CH4, C2 H2, C2H4, C2H6 and But-1-ene Studied Between 23 and 295 K with a CRESU Apparatus Astron. Astrophys. 1997, 323, 644-651
20. Turner, B. E.; Zuckerman, B. Microwave Detection of Interstellar CH Astrophys. J. 1974, 187, L59-62
21. Rydbeck, O. E. H.; Ellder, J.; Irvine, W. M. Radio Detection of Interstellar CH Nature 1973, 246, 466-468
22. Lien, D. J. A Reanalysis of the Interstellar CH Abundance Astrophys. J. 1984, 284, 578-588
23. Arpigny, C. Spectra of Comets and Their Interpretation Annu. Rev. Astron. Astrophys. 1965, 3, 351-376
24. Ridgway, S. T.; Carbon, D. F.; Hall, D. N. B.; Jewell, J. An Atlas of Late-type Stellar Spectra, 2400-2778 Inverse Centimeters Astrophys. J. Suppl. 1984, 54, 177-209
25. Lambert, D. L.; Gustafsson, B.; Eriksson, K.; Hinkle, K. H. The Chemical Composition of Carbon Stars: I. Carbon, Nitrogen, and Oxygen in 30 Cool Carbon Stars in the Galactic Disk Astrophys. J. Suppl. 1986, 62, 373-425
26. Thoman, J. W.; McIlroy, A. Absolute CH Radical Concentrations in Rich Low-pressure Methane-oxygen-argon Flames via Cavity Ringdown Spectroscopy of the A(2) Delta-(XII)-I-2 Transition J. Phys. Chem. A 2000, 104, 4953-4961
27. Lockyear, J. F.; Welz, O.; Savee, D. J.; Goulay, F.; Trevitt, J. A.; Taatjes, A. C.; Osborn, D. L.; Leone, S. R. Isomer Specific Product Detection in the Reaction of CH with Acrolein J. Phys. Chem. A 2013, 117, 11013-11026
28. Becke, A. D. Density-functional Thermochemistry. III. The Role of Exact Exchange J. Chem. Phys. 1993, 98, 5648-5652
29. 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, 785-789
30. Vosko, S. H.; Wilk, L.; Nusair, M. Accurate Spin-dependent Electron Liquid Correlation Energies for Local Spin Density Calculations: A Critical Analysis Can. J. Phys. 1980, 58, 1200-1211
31. Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. Ab-initio Calculation of Vibrational Absorption and Circular Dichroism Spectra Using Density Functional Force Fields J. Phys. Chem. 1994, 98, 11623-11627
32. Montgomery, J. A.; Frisch, M. J.; Ochterski, J. W.; Petersson, G. A. A Complete Basis Set Model Chemistry. VI. Use of Density Functional Geometries and Frequencies J. Chem. Phys. 1999, 110, 2822-2827
33. Montgomery, J. A.; Frisch, M. J.; Ochterski, J. W.; Petersson, G. A. A Complete Basis Set Model Chemistry. VII. Use of the Minimum Population Localization Method J. Chem. Phys. 2000, 112, 6532-6542
34. Klippenstein, S. J. Variational Optimizations in the Rice-Ramsberger-Kassel-Marcus Theory Calculations for Unimolecular Dissociations with no Reverse Barrier J. Chem. Phys. 1992, 96, 367-371
35. Klippenstein, S. J.; Marcus, R. A. High Pressure Rate Constants for Unimolecular Dissociation/Free Radical Recombination: Determination of the Quantum Correction via Quantum Monte Carlo Path Integration J. Chem. Phys. 1987, 87, 3410-3417
36. Wardlaw, D. M.; Marcus, R. A. RRKM Reaction Rate Theory for Transition States of any Looseness Chem. Phys. Lett. 1984, 110, 230-234
37. Wardlaw, D. M.; Marcus, R. A. Unimolecular Reaction Rate Theory for Transition States of Partial Looseness. II. Implementation and Analysis with Applications to NO2 and C2H6 Dissociations J. Chem. Phys. 1985, 83, 3462-3480
38. Goulay, F.; Trevitt, A. J.; Meloni, G.; Selby, T. M.; Osborn, D. L.; Taatjes, C. A.; Vereecken, L.; Leone, S. R. Cyclic Versus Linear Isomers Produced by Reaction of the Methylidyne Radical (CH) with Small Unsaturated Hydrocarbons J. Am. Chem. Soc. 2009, 131, 993-1005
39. Trevitt, A. J.; Prendergast, M. B.; Goulay, F.; Savee, J. D.; Osborn, D. L.; Taatjes, C. A.; Leone, S. R. Product Branching Fractions of the CH + Propene Reaction from Synchrotron Photoionization Mass Spectrometry J. Phys. Chem. A 2013, 117, 6450-6457
40. Goulay, F.; Trevitt, A. J.; Savee, J. D.; Bouwman, J.; Osborn, D. L.; Taatjes, C. A.; Wilson, K. R.; Leone, S. R. Product Detection of the CH Radical Reaction with Acetaldehyde J. Phys. Chem. A 2012, 116, 6091-6106
41. Goulay, F.; Derakhshan, A.; Maher, E.; Trevitt, A. J.; Savee, J. D.; Scheer, A. M.; Osborn, D. L.; Taatjes, C. A. Formation of Dimethylketene and Methacrolein by Reaction of the CH Radical with Acetone Phys. Chem. Chem. Phys. 2013, 15, 4049-4058
42. Soorkia, S.; Taatjes, C. A.; Osborn, D. L.; Selby, T. M.; Trevitt, A. J.; Wilson, K. R.; Leone, S. R. Direct Detection of Pyridine Formation by the Reaction of CH (CD) with Pyrrole: A Ring Expansion Reaction Phys. Chem. Chem. Phys. 2010, 12, 8750-8758
43. Hammond, B. L.; Lester, W. A., Jr.; Reynolds, P. J. Monte Carlo Methods in Ab Initio Quantum Chemistry, Vol. 1 of World Scientific Lecture and Course Notes in Chemistry; World Scientific: Singapore, 1994.
44. Anderson, J. B. In Reviews in Computational Chemistry; Lipkowitz, K. B.; Boyd, D. B., Eds.; John Wiley and Sons: New York, 1999; Vol. 13, pp 133-182.
45. Ceperley, D. M.; Mitas, L. In New Methods in Computational Quantum Mechanics; Prigogine, I.; Rice, S. A., Eds.; John Wiley and Sons: New York, 1996; Vol. 93, pp 1-38.
46. Foulkes, W. M. C.; Mitas, L.; Needs, R. J.; Rajagopal, G. Quantum Monte Carlo Simulations of Solids Rev. Mod. Phys. 2001, 73, 33-83
47. Helgaker, T.; Jorgensen, P.; Jeppe, O. Molecular Electronic-Structure Theory; John Wiley and Sons: Chichester, UK, 2000.
48. Szabo, A.; Ostlund, N. Modern Quantum Chemistry: Introduction to Advanced Electronic Structure Theory; McGraw-Hill: New York, 1989.
49. Zhao, Y.; Truhlar, D. 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 Theor. Chem. Acc. 2008, 120, 215-241
50. Head-Gordon, M.; Pople, J. A.; Frisch, M. J. MP2 Energy Evaluation by direct methods Chem. Phys. Lett. 1988, 153, 503-506
51. Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. Self-consistent Molecular Orbital Methods. XX. A Basis Set for Correlated Wave Functions J. Chem. Phys. 1980, 72, 650-654
52. Gonzales, C.; Schlegel, H. B. An Improved Algorithm for Reaction Path Following J. Chem. Phys. 1989, 90, 2154-2161
53. Gonzales, C.; Schlegel, H. B. Reaction Path Following in Mass-weighted Internal Coordinates J. Phys. Chem. 1990, 94, 5523-5527
54. Jensen, F. Introduction to Computational Chemistry; John Wiley and Sons: New York, 1999; p 189.
55. Baker, J.; Scheiner, A.; Andzelm, J. Spin Contamination in Density Functional Theory Chem. Phys. Lett. 1993, 216, 380-388
56. Montoya, A.; Truong, T. N.; Sarofim, A. F. Spin Contamination in Hartree-Fock and Density Functional Theory Wavefunctions in Modeling of Adsorption on Graphite J. Phys. Chem. A 2000, 104, 6108-6110
57. Wittbrodt, J. M.; Schlegel, H. B. Some Reasons not to Use Spin Projected Density Functional Theory J. Chem. Phys. 1996, 105, 6574-6577
58. Cioslowski, J.; Liu, G.; Martinov, M.; Piskorz, P.; Moncrieff, D. Energetics and Site Specificity of the Homolytic C-H Bond Cleavage in Benzenoid Hydrocarbons: An ab Initio Electronic Structure Study J. Am. Chem. Soc. 1996, 118, 5261-5264
59. Murray, C. W.; Handy, N. C.; Amos, R. D. A study of O3, S3, CH2, and Be2 using Kohn-Sham theory with accurate quadrature and large basis sets J. Chem. Phys. 1993, 98, 7145-7151
60. Pople, J. A.; Gill, P. M. W.; Handy, N. C. Spin-Unrestricted Character of Khon-Sham Orbitals for Open-Shell Systems Int. J. Quantum Chem. 1995, 56, 303-305
61. Gordon, M. S.; Schmidt, M. W. Theory and Applications of Computational Chemistry: The First Forty Years; Elsevier: Amsterdam, 2005.
62. Schmidt, M. W.; Baldridge, K. K.; Boatz, J. A.; Elbert, S. T.; Gordon, M. S.; Jensen, J. H.; Koseki-Matsunaga, S. N.; Nguyen, K. A.; Su, S. J.; Windus, T. L.; Dupuis, M.; Montgomery, J. A. General Atomic and Molecular Electronic Structure System J. Comput. Chem. 1993, 14, 1347-1363
63. Aspuru-Guzik, A.; Salomon-Ferrer, R.; Austin, B.; Perusquia-Flores, R.; Griffin, M. A.; Oliva, R. A.; Skinner, D.; Domin, D.; Lester, W. A., Jr. Software News and Updates Zori 1.0: A Parallel Quantum Monte Carlo Electronic Structure Package J. Comput. Chem. 2005, 26, 856-862
64. Schmidt, K. E.; Moskowitz, J. W. Correlated Monte Carlo Wave Functions for the Atoms He Through Ne J. Chem. Phys. 1990, 93, 4172-4178
65. Boys, S. F.; Handy, N. C. The Determination of Energies and Wavefunctions with Full Electronic Correlation Proc. R. Soc. London, Ser. A 1969, 310, 43-61
66. Reynolds, P. J.; Ceperley, D. M.; Alder, B. J.; Lester, W. A., Jr. Fixed-node Quantum Monte Carlo for Molecules J. Chem. Phys. 1982, 77, 5593-5603
67. Toulouse, J.; Umrigar, C. J. Optimization of Quantum Monte Carlo Wave Functions by Energy Minimization J. Chem. Phys. 2007, 126, 084102-1-084102-16
68. Nicolaides, A.; Rauk, A.; Glukhovtsev, M. N.; Radom, L. Heats of Formation from G2, G2(MP2), and G2(MP2,SVP) Total Energies J. Phys. Chem. 1996, 100, 17460-17464
69. Chase, M. W., Jr.; Davies, C. A.; Downey, J. R., Jr.; Frurip, D. J.; McDonald, R. A.; Syverud, A. N. JANAF Thermochemical Tables, 3 rd ed. J. Phys. Chem. Ref. Data 1985, 14, Suppl. No. 1.
70. Lias, S. G.; Bartmess, J. E.; Liebman, J. F.; Holmes, J. L.; Levin, R. D.; Mallard, W. G. Gas-phase Ion and Neutral Thermochemistry. J. Phys. Chem. Ref. Data 1988, 17, Suppl. No. 1.
71. Kollias, A. C.; Couronne, O.; Lester, W. A., Jr. Quantum Monte Carlo Study of the Reaction: Cl + CH3OH→ CH2OH + HCl J. Chem. Phys. 2004, 121, 1357-1363
72. Barker, J. R. Multiple-Well, Multiple-Path Unimolecular Reaction Systems. I. MultiWell Computer Program Suite Int. J. Chem. Kinet. 2001, 33, 232-245
73. Barker, J. R. Energy Transfer in Master Equation Simulations: A New Approach Int. J. Chem. Kinet. 2009, 41, 748-763
74. Barker, J. R.; Ortiz, N. F.; Preses, J. M.; Lohr, L. L.; Maranzana, A.; Stimac, P. J.; Nguyen, T. L.; Kumar, T. J. D. MultiWell Software (v. 2014.1); University of Michigan: Ann Arbor, MI, 2013.
75. Gillespie, D. T. Exact Stochastic Simulation of Coupled Chemical Reactions J. Phys. Chem. 1977, 81, 2340
76. Gillespie, D. T. Markov Processes: An Introduction for Physical Scientists; Academic Press: San Diego, CA, 1992.
77. Huber, K.; Herzberg, G. Molecular Spectra and Molecular Structure 4. Constants of Diatomic Molecules; van Nostrand: Princeton, 1979.
78. Pople, J. A.; Head-Gordon, M.; Fox, D. J.; Raghavachari, K.; Curtiss, L. A. Gaussian-1 Theory: A General Procedure for Prediction of Molecular Energies J. Chem. Phys. 1989, 90, 5622-5629
79. Curtiss, L. A.; Jones, C.; Trucks, W.; Raghavachari, K.; Pople, J. A. Gaussian-1 Theory of Molecular Energies for Second-row Compounds J. Chem. Phys. 1990, 93, 2537-2545
80. Grossman, J. Benchmark Quantum Monte Carlo Calculations J. Chem. Phys. 2002, 117, 1434-1440
81. Feller, D.; Peterson, K. A. Re-examination of Atomization Energies for the Gaussian-2 Set of Molecules J. Chem. Phys. 1999, 110, 8384-8396
82. Pedley, J. B. Thermodynamic Data and Structures of Organic Compounds; Thermodynamics Research Center: College Station, TX, 1994; Vol. 1.
83. Ruscic, B.; Boggs, J. E.; Burcat, A.; Csaszar, A. G.; Demasison, J.; Janoschek, R.; Martin, J. M. L.; Morton, M. L.; Rossi, M. J.; Stanton, J. F.; Sazalay, P. G.; Westmoreland, P. R.; Zabel, F.; Berces, T. IUPAC Critical Evaluation of Thermochemical Properties of Selected Radicals. Part I J. Phys. Chem. Ref. Data 2005, 34, 573-656
84. Asatryan, R.; Silva, G.; da Bozzelli, J. W. Quantum Chemical Study of the Acrolein (CH2CHCHO) + OH + O2 Reactions J. Phys. Chem. A 2010, 114, 8302-8311
85. Li, Y.; Baer, T. The Dissociation Dynamics and Thermochemistry of the Acrolein Ion Studied by Threshold Photoelectron-photoion Coincidence Spectroscopy Int. J. Mass Spectrom. 2002, 218, 37-48
86. Rodriquez, C. F.; Bohme, D. K.; Hopkinson, A. C. Theoretical Enthalpies of Formation of CHmCln: Neutral Molecules and Cations J. Phys. Chem. 1996, 100, 2942-2949
87. Feller, D.; Franz, J. A. A Theoretical Determination of the Heats of Formation of Furan, Tetrahydrofuran, THF-2-yl, and THF-3-yl J. Phys. Chem. A 2000, 104, 9017-9025
88. Curtiss, L. A.; Raghavachari, K.; Redfern, P. C.; Pople, J. A. Assessment of Gaussian-2 and Density Functional Theories for the Computation of Enthalpies of Formation J. Chem. Phys. 1997, 106, 1063-1079