Theoretical study of the thermal decomposition of dimethyl disulfide

Journal of Physical Chemistry A

Volumn 114, Issue 39, 2010, Pages 10531-10549

  Vandeputte, Aäron G ^a   Reyniers, Marie Françoise ^a   Marin, Guy B ^a  

^a GHENT UNIVERSITY   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

BOND DISSOCIATION ENERGIES; BOND DISSOCIATION ENTHALPIES; CBS-QB3; COMPOSITE METHOD; DECOMPOSITION MECHANISM; DECOMPOSITION PRODUCTS; DIMETHYL DISULFIDES; ENTHALPIES OF FORMATION; EXPERIMENTAL OBSERVATION; EXPERIMENTAL STUDIES; FIRST-ORDER RATES; HIGH-PRESSURE LIMITS; KINETIC MODELS; MEAN ABSOLUTE DEVIATIONS; ORDER OF MAGNITUDE; ORGANOSULFUR COMPOUNDS; PRESSURE LIMITS; PRODUCT SELECTIVITIES; RATE COEFFICIENTS; REACTION MECHANISM; REACTION PATHS; STANDARD ENTHALPIES OF FORMATION; THEORETICAL STUDY; THERMAL DECOMPOSITION MECHANISM; THERMAL DECOMPOSITIONS; THERMO CHEMICAL PROCESS; THERMOCHEMICAL DATA; THIYL RADICALS;

CHEMICAL BONDS; DISSOCIATION; ELECTRIC CIRCUIT BREAKERS; ENTHALPY; KINETIC THEORY; PYROLYSIS; SULFUR;

CARBON DISULFIDE;

DIMETHYL DISULFIDE; DISULFIDE;

ARTICLE; CHEMISTRY; COMPUTER SIMULATION; KINETICS; THERMODYNAMICS;

COMPUTER SIMULATION; DISULFIDES; KINETICS; THERMODYNAMICS;

EID: 77957299394     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp103357z     Document Type: Article

References (99)

1. Barnes, I.; Hjorth, J.; Mihalopoulos, N. Dimethyl sulfide and dimethyl sulfoxide and their oxidation in the atmosphere Chem. Rev. (Washington, DC, U. S.) 2006, 106, 940
2. Mousavipour, S. H.; Emad, L.; Fakhraee, S. Theoretical study on the unimolecular dissociation of CH3SCH3 and CH3SCH2 J. Phys. Chem. A 2002, 106, 2489
3. Riffault, V.; Bedjanian, Y.; Le Bras, G. Kinetics and mechanism of the O atom reaction with dimethyl sulfoxide J. Phys. Chem. A 2003, 107, 5404
4. Borissenko, D.; Kukui, A.; Laverdet, G.; Le Bras, G. Experimental study of SO2 formation in the reactions of CH3SO radical with NO2 and O-3 in relation with the atmospheric oxidation mechanism of dimethyl sulfide J. Phys. Chem. A 2003, 107, 1155
5. Petherbridge, J. R.; May, P. W.; Shallcross, D. E.; Harvey, J. N.; Fuge, G. M.; Rosser, K. N.; Ashfold, M. N. R. Simulation of H-C-S containing gas mixtures relevant to diamond chemical vapour deposition Diamond Relat. Mater. 2003, 12, 2178
6. Wang, J.; Reyniers, M. F.; Marin, G. B. Influence of dimethyl disulfide on coke formation during steam cracking of hydrocarbons Ind. Eng. Chem. Res. 2007, 46, 4134
7. Bin, C.; Badi, N.; nevault-Celton, V.; Cheradame, H. Study of the interactions of organic sulfides with active species in the cationic polymerization of 1,3-pentadiene Polym. Bull. (Berlin) 2004, 51, 343
8. Tsuda, K.; Kobayash, S.; Otsu, T. Vinyl Polymerization 0.116. Effects of Several Sulfides and Oxides on Radical Polymerization Bull. Chem. Soc. Jpn. 1965, 38, 1517
9. Andrzejewska, E. The Influence of Aliphatic Sulfides on the Photoinduced Polymerization of Butanediol-1,4 Dimethacrylate J. Polym. Sci., Part A: Polym. Chem. 1992, 30, 485
10. Andrzejewska, E. The Effect of Aliphatic Sulfides on the Photopolymerization of Diacrylates Polymer 1993, 34, 3899
11. Texier, S.; Berhault, G.; Perot, G.; Harle, V.; Diehl, F. Activation of alumina-supported hydrotreating catalysts by organosulfides: comparison with H2S and effect of different solvents J. Catal. 2004, 223, 404
12. Texier, S.; Berhault, G.; Perot, G.; Diehl, F. Activation of alumina-supported hydrotreating catalysts by organosulfides or H2S: Effect of the H2S partial pressure used during the activation process Appl. Catal., A 2005, 293, 105
13. Hallie, H. Experience Reveals Best Presulfiding Techniques for Hds and Hdn Catalysts Oil Gas J. 1982, 80, 69
14. Coope, J. A. R.; Bryce, W. A. The thermal decomposition of dimethyl disulfide Can. J. Chem. 1954, 32
15. Braye, E.; Sehon, A.; Darwent, B. Thermal decomposition of sulfides J. Am. Chem. Soc. 1955, 77, 5282
16. Bock, H.; Mohmand, S. Unstable Intermediates in Gaseous Phase 0.6. Thermal-Decomposition of Alkyl Sulfides Rsnr Angew. Chem., Int. Ed. Engl. 1977, 16, 104
17. Kroto, H. W.; Suffolk, R. J. Photoelectron Spectrum of An Unstable Species in Pyrolysis Products of Dimethyldisulfide Chem. Phys. Lett. 1972, 15, 545
18. Shum, L. G. S.; Benson, S. W. The Pyrolysis of Dimethyl Sulfide, Kinetics and Mechanism Int. J. Chem. Kinet. 1985, 17, 749
19. Zheng, X.; Fisher, E. M.; Gouldin, F. C.; Zhu, L.; Bozzelli, J. W. Experimental and computational study of diethyl sulfide pyrolysis and mechanism Proc. Combust. Inst. 2009, 32, 469
20. Senning, A.; Hansen, H. C.; Abdelmegeed, M. F.; Mazurkiewicz, W.; Jensen, B. Studies of Dithiiranes and Thiosulfines As Reactive Intermediates Tetrahedron 1986, 42, 739
21. Senning, A. Dithiiranes and Thiosulfines As Reactive Intermediates Angew. Chem., Int. Ed. Engl. 1979, 18, 941
22. Ishii, A.; Hoshino, M.; Nakayama, J. Recent advances in chemistry of dithiirane and small ring compounds containing two chalcogen atoms Pure Appl. Chem. 1996, 68, 869
23. Mloston, G.; Romanski, J.; Reisenauer, H. P.; Maier, G. Thioformaldehyde S-sulfide (thiosulfine) Angew. Chem., Int. Ed. 2001, 40, 393
24. Martin, G.; Drayer, A.; Ropero, M.; Alonso, M. E. Gas-Phase Thermolysis of Sulfur-Compounds 0.3.-Normal-Butyl2-Propenyl Sulfide Int. J. Chem. Kinet. 1982, 14, 131
25. Martin, G.; Barroeta, N. Gas-Phase Thermolysis of Sulfur-Compounds 0.1. Di-T-Butyl Disulfide J. Chem. Soc., Perkin Trans. 2 1976, 1421
26. Martin, G.; Barroeta, N. Gas-Phase Thermolysis of Sulfur-Compounds 0.2. Ditertiary Butyl Sulfide Int. J. Chem. Kinet. 1980, 12, 699
27. Benson, S. W. Thermochemistry and Kinetics of Sulfur-Containing Molecules and Radicals Chem. Rev. (Washington, DC, U. S.) 1978, 78, 23
28. Benson, S. W.; Cruicksh, Fr.; Golden, D. M.; Haugen, G. R.; Oneal, H. E.; Rodgers, A. S.; Shaw, R.; Walsh, R. Additivity Rules for Estimation of Thermochemical Properties Chem. Rev. (Washington, DC, U.S.) 1969, 69, 279
29. Benson, S. W. Current status of group additivity Abstr. Pap. Am. Chem. Soc. 1996, 212, 56
30. Vandeputte, A. G.; Reyniers, M. F.; Marin, G. B. A theoretical study of the thermodynamics and kinetics of small organosulfur compounds Theor. Chem. Acc. 2009, 123, 391
31. Izgorodina, E. I.; Coote, M. L.; Radom, L. Trends in R-X bond dissociation energies (R = Me, Et, i-Pr, t-Bu; X = H, CH3, OCH3, OH, F): A surprising shortcoming of density functional theory J. Phys. Chem. A 2005, 109, 7558
32. Schwabe, T.; Grimme, S. Theoretical thermodynamics for large molecules: Walking the thin line between accuracy and computational cost Acc. Chem. Res. 2008, 41, 569
33. Steudel, R.; Steudel, Y.; Lentz, D. Tetraamidosulfurane and its decomposition products-an ab initio MO study Eur. J. Inorg. Chem. 2002, 2557
34. Steudel, Y.; Steudel, R.; Wong, M. W. The thermal decomposition of thiirane: A mechanistic study by ab initio MO theory Chem. - Eur. J. 2002, 8, 217
35. Steudel, R.; Steudel, Y. The thermal decomposition of S2O forming SO2, S-3, S-4 and S5O-An ab initio MO study Eur. J. Inorg. Chem. 2004, 3513
36. Kee, R. J.; Miller, J. A.; Jefferson, T. H. CHEMKIN: A General-Purpose, Problem-Independent, Transportable, Fortran Chemical Kinetics Package; Sandia National Laboratories, 1980.
37. Kee, R. J.; Rupley, F. M.; Miller, J. A.; Coltrin, M. E.; Grcar, J. F.; Meeks, E.; Moffat, H. K.; Lutz, A. E.; Dixon-Lewis, G.; Smooke, M. D.; Warnatz, J.; Evans, G. H.; Larson, R. S.; Mitchell, R. E.; Petzold, L. R.; Reynolds, W. C.; Caracotsios, M.; Stewart, W. E.; Glarborg, P.; Wang, C.; McLellan, C. L.; Adigun, O.; Houf, W. G.; Chou, C. P.; Miller, S. F.; Ho, P.; Young, P. D.; Young, J.; Hodgson, D. W.; Petrova, M. V.; Puduppakkam, K. V. CHEMKIN Release 4.1.1; San Diego, CA, 2007.
38. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; AustinA., J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision C.02; Gaussian, Inc.: Wallingford, CT, 2004.
39. Adamo, C.; Barone, V. Exchange functionals with improved long-range behavior and adiabatic connection methods without adjustable parameters: The mPW and mPW1PW models J. Chem. Phys. 1998, 108, 664
40. Boese, A. D.; Martin, J. M. L. Development of density functionals for thermochemical kinetics J. Chem. Phys. 2004, 121, 3405
41. 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
42. Curtiss, L. A.; Raghavachari, K.; Redfern, P. C.; Rassolov, V.; Pople, J. A. Gaussian-3 (G3) theory for molecules containing first and second-row atoms J. Chem. Phys. 1998, 109, 7764
43. Baboul, A. G.; Curtiss, L. A.; Redfern, P. C.; Raghavachari, K. Gaussian-3 theory using density functional geometries and zero-point energies J. Chem. Phys. 1999, 110, 7650
44. Luo, Y.-R. Handbook of bond dissociation energies in organic compounds; CRC Press: Boca Raton, FL, 2003.
45. Cramer, C. J. Essentials of computational chemistry: theories and models, 2nd ed.; Wiley: Chichester, West Sussex, England, and Hoboken, NJ, 2004.
46. Andersson, M. P.; Uvdal, P. New scale factors for harmonic vibrational frequencies using the B3LYP density functional method with the triple-xi basis set 6-311+G(d,p) J. Phys. Chem. A 2005, 109, 2937
47. Van Speybroeck, V.; Van Neck, D.; Waroquier, M.; Wauters, S.; Saeys, M.; Marin, G. B. Ab initio study of radical addition reactions: Addition of a primary ethylbenzene radical to ethene (I) J. Phys. Chem. A 2000, 104, 10939
48. Vansteenkiste, P.; Van Neck, D.; Van Speybroeck, V.; Waroquier, M. An extended hindered-rotor model with incorporation of Coriolis and vibrational-rotational coupling for calculating partition functions and derived quantities J. Chem. Phys. 2006, 124, 044314
49. Khan, S. S.; Yu, X. R.; Wade, J. R.; Malmgren, R. D.; Broadbelt, L. J. Thermochemistry of Radicals and Molecules Relevant to Atmospheric Chemistry: Determination of Group Additivity Values using G3//B3LYP Theory J. Phys. Chem. A 2009, 113, 5176
50. Chen, C. C.; Bozzelli, J. W. Structures, intramolecular rotation barriers, and thermochemical properties of methyl ethyl, methyl isopropyl, and methyl tert -butyl ethers and the corresponding radicals J. Phys. Chem. A 2003, 107, 4531
51. Sumathi, R.; Carstensen, H. H.; Green, W. H. Reaction rate prediction via group additivity, part 2: H-abstraction from alkenes, alkynes, alcohols, aldehydes, and acids by H atoms J. Phys. Chem. A 2001, 105, 8969
52. Sumathi, R.; Carstensen, H. H.; Green, W. H. Reaction rate prediction via group additivity Part 1: H abstraction from alkanes by H and CH3 J. Phys. Chem. A 2001, 105, 6910
53. Vansteenkiste, P.; Verstraelen, T.; Van Speybroeck, V.; Waroquier, M. Ab initio calculation of entropy and heat capacity of gas-phase n -alkanes with hetero-elements O and S: Ethers/alcohols and sulfides/thiols Chem. Phys. 2006, 328, 251
54. Laidler, K. J. Chemical kinetics, 3rd ed.; Harper & Row: New York, 1987.
55. Vandeputte, A. G.; Sabbe, M. K.; Reyniers, M. F.; Van Speybroeck, V.; Waroquier, M.; Marin, G. B. Theoretical study of the thermodynamics and kinetics of hydrogen abstractions from hydrocarbons J. Phys. Chem. A 2007, 111, 11771
56. Eckart, W. U. The penetration of a potential barrier by electrons Phys. Rev. 1930, 35
57. Truhlar, D. G.; Garrett, B. C. Variational Transition-State Theory Acc. Chem. Res. 1980, 13, 440
58. Duncan, W. T.; Bell, R. L.; Truong, T. N. TheRate: Program for ab initio direct dynamics calculations of thermal and vibrational-state-selected rate constants J. Comput. Chem. 1998, 19, 1039
59. Eade, R. H. A.; Robb, M. A. Direct Minimization in Mc Scf Theory-the Quasi-Newton Method Chem. Phys. Lett. 1981, 83, 362
60. Sendt, K.; Haynes, B. S. Quantum chemical and RRKM calculations of reactions in the H/S/O system Proc. Combust. Inst. 2007, 31, 257
61. Benassi, R.; Taddei, F. A theoretical ab initio approach to the S-S bond breaking process in hydrogen disulfide and in its radical anion J. Phys. Chem. A 1998, 102, 6173
62. Qi, F.; Sheng, L.; Ahmed, M.; Peterka, D. S.; Baer, T. Exclusive production of excited-state sulfur (D-1) atoms from 193 nm photolysis of thietane Chem. Phys. Lett. 2002, 357, 204
63. Beljonne, D.; Shuai, Z.; Pourtois, G.; Bredas, J. L. Spin-orbit coupling and intersystem crossing in conjugated polymers: A configuration interaction description J. Phys. Chem. A 2001, 105, 3899
64. 2S+S J. Phys. Chem. A 2008, 112, 3239
65. Robertson, S. H.; Wardlaw, D. M.; Wagner, A. F. Flexible transition state theory for a variable reaction coordinate: Derivation of canonical and microcanonical forms with angular momentum conservation J. Chem. Phys. 2002, 117, 593
66. Robertson, S.; Wagner, A. F.; Wardlaw, D. M. Flexible transition state theory for a variable reaction coordinate: Analytical expressions and an application J. Phys. Chem. A 2002, 106, 2598
67. Robertson, S. H.; Wagner, A. F.; Wardlaw, D. M. Canonical Flexible Transition-State Theory Revisited J. Chem. Phys. 1995, 103, 2917
68. Grabowy, J. A. D.; Mayer, P. M. Entropy changes in the dissociation of proton-bound complexes: A variational RRKM study J. Phys. Chem. A 2004, 108, 9726
69. Grabowy, J. A. D.; Mayer, P. M. Entropy changes in the dissociation of proton-bound complexes: A variational RRKM study J. Phys. Chem. A 2005, 109, 5243
70. Langhoff, S. R.; Sink, M. L.; Pritchard, R. H.; Kern, C. W. Theoretical-Study of the Spin-Orbit-Coupling in the X2-Pi State of OH J. Mol. Spectrosc. 1982, 96, 200
71. 3S with ClO J. Mol. Struct.: THEOCHEM 2008, 866, 46
72. • J. Chem. Theory Comput. 2005, 1, 1162
73. Bond, D. Computational methods in organic thermochemistry. 2. Enthalpies and free energies of formation for functional derivatives of organic hydrocarbons J. Org. Chem. 2007, 72, 7313
74. do Couto, P. C.; Cabral, B. J. C.; Simoes, J. A. M. S-H bond dissociation enthalpies: The importance of a complete basis set approach Chem. Phys. Lett. 2006, 421, 504
75. Benassi, R.; Fiandri, G. L.; Taddei, F. A theoretical MO ab initio approach to the conformational properties and homolytic bond cleavage in aryl disulphides J. Mol. Struct.: THEOCHEM 1997, 418, 127
76. Zou, L. F.; Fu, Y.; Shen, K.; Guo, Q. X. Sulfur-sulfur bond dissociation enthalpies: A high-level ab initio study J. Mol. Struct.: THEOCHEM 2007, 807, 87
77. Cerru, F. G.; Kronenburg, A.; Lindstedt, R. P. Systematically reduced chemical mechanisms for sulfur oxidation and pyrolysis Combust. Flame 2006, 146, 437
78. 2S thermolysis and H-2 sulfidation Proc. Combust. Inst. 2003, 29, 2439
79. Wong, B. M.; Matheu, D. M.; Green, W. H. Temperature and molecular size dependence of the high-pressure limit J. Phys. Chem. A 2003, 107, 6206
80. Troe, J. Detailed modeling of the temperature and pressure dependence of the reaction H + O-2(+ M) → HO2(+ M) Proc. Combust. Inst. 2000, 28, 1463
81. Kice, J. Sulfur-centered radicals. In Free Radicals Vol. I 1973; Vol. I, p 711.
82. Cox, J. D.; Wagman, D. D.; Medvedev, V. A. CODATA Key Values for Thermodynamics; Hemisphere Publishing Corp.: New York, 1984.
83. Wilson, S. H. S.; Howe, J. D.; Ashfold, M. N. R. On the near ultraviolet photodissociation of hydrogen sulphide Mol. Phys. 1996, 88, 841
84. Chase, M. W. NIST-JANAF thermochemical tables, 4th ed.; American Chemical Society and American Institute of Physics for the National Institute of Standards and Technology: Washington, DC, and Woodbury, NY, 1998.
85. Berkowitz, J.; Ellison, G. B.; Gutman, D. 3 Methods to Measure Rh Bond-Energies J. Phys. Chem. 1994, 98, 2744
86. Alfassi, Z. B. S-centered radicals. In The chemistry of free radicals; Wiley: Chichester and New York, 1999.
87. dos Santos, R. M. B.; Muralha, V. S. F.; Correia, C. F.; Guedes, R. C.; Cabral, B. J. C.; Simoes, J. A. M. S-H bond dissociation enthalpies in thiophenols: A time-resolved photoacoustic calorimetry and quantum chemistry study J. Phys. Chem. A 2002, 106, 9883
88. - Abstr. Pap. Am. Chem. Soc. 1993, 205, 28
89. Howari, J. A.; Griller, D.; Lossing, F. P. Thermochemistry of Perthiyl Radicals J. Am. Chem. Soc. 1986, 108, 3273
90. Good, W. D.; Lacina, J. L.; Mccullough, J. P. Methanethiol and Carbon Disulfide-Heats of Combustion and Formation by Rotating-Bomb Calorimetry J. Phys. Chem. 1961, 65, 2229
91. Ruscic, B.; Berkowitz, J. Photoionization Mass-Spectrometry of Ch2S and Hcs J. Chem. Phys. 1993, 98, 2568
92. Mccullough, J. P.; Hubbard, W. N.; Frow, F. R.; Hossenlopp, I. A.; Waddington, G. Ethanethiol and 2-Thiapropane-Heats of Formation and Isomerization-the Chemical Thermodynamic Properties from 0 to 1000 K J. Am. Chem. Soc. 1957, 79, 561
93. Frenkel, M. L. Thermodynamics of organic compounds in the gas state; Texas Engineering Experiment Station Thermodynamics Research Center: College Station, TX, 1994
94. nR (M = S, Se, Te; n = 1, 2) Dokl. Akad. Nauk SSSR 1989, 307, 1139
95. Shim, I.; Baba, M. S.; Gingerich, K. A. Electronic structure of Ge-2 and Ge-2 and thermodynamic properties of Ge-2 from all electron ab initio investigations and Knudsen effusion mass spectroscopic measurements Chem. Phys. 2002, 277, 9
96. 3S Radicals J. Phys. Chem. 1992, 96, 2518
97. 3 J. Chem. Phys. 1990, 92, 6587
98. NIST Chemistry webbook, Standard Reference Database 69; http://webbook.nist.gov/, June 2005.
99. Lide, D. E. CRC handbook of chemistry and physics, 82th ed.; CRC Press: Boca Raton, FL, 2002.