Thermochemistry and bond dissociation energies of ketones

Journal of Physical Chemistry A

Volumn 116, Issue 23, 2012, Pages 5707-5722

  Hudzik, Jason M ^a   Bozzelli, Joseph W ^a  

^a NEW JERSEY INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ATMOSPHERIC CHEMISTRY; ATOMS; CHEMICAL STABILITY; COMBUSTION; DISSOCIATION; ELECTRIC CIRCUIT BREAKERS; ENTHALPY; ENTROPY; HYDROCARBONS; HYDROGEN BONDS; ORGANIC CHEMICALS; REACTION INTERMEDIATES; REACTION KINETICS; SPECIFIC HEAT;

BOND DISSOCIATION ENERGIES; CARBON-HYDROGEN BOND; COMBUSTION PRO-CESS; DENSITY-FUNCTIONAL LEVEL; HYDROGEN BOND INCREMENTS; ISODESMIC REACTIONS; STANDARD ENTHALPIES OF FORMATION; THERMOCHEMICAL PROPERTIES;

KETONES;

EID: 84862270468     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp302830c     Document Type: Article

References (98)

1. Lewis, A. C.; Hopkins, J. R.; Carpenter, L. J.; Stanton, J.; Read, K. A.; Pilling, M. J. Atmos. Chem. Phys. 2005, 5, 1963-1974
2. Singh, H. B.; Salas, L. J.; Chatfield, R. B.; Czech, E.; Fried, A.; Walega, J.; Evans, M. J.; Field, B. D.; Jacob, D. J.; Blake, D. J. Geophys. Res. 2004, 109, D15S07
3. Arnold, F.; Knop, G.; Ziereis, H. Nature 1986, 321, 505-507
4. Jaeglé, L.; Jacob, D. J.; Brune, W. H.; Wennberg, P. O. Atmos. Environ. 2001, 35, 469-489
5. Singh, H. B.; Kanakidou, M.; Crutzen, P. J.; Jacob, D. J. Nature 1995, 378, 50-54
6. Warneke, C.; Karl, T.; Judmaier, H.; Hansel, A.; Jordan, A.; Lindinger, W.; Crutzen, P. J. Global Biogeochem. Cycles 1999, 13, 9-17
7. Jacob, D. J.; Field, B. D.; Jin, E. M.; Bey, I.; Li, Q.; Logan, J. A.; Yantosca, R. M.; Singh, H. B. J. Geophys. Res. 2002, 107, 5-1-5-17
8. Gierczak, T.; Burkholder, J. B.; Bauerle, S.; Ravishankara, A. R. Chem. Phys. 1998, 231, 229-244
9. Singh, H. B.; Herlth, D.; O'Hara, D.; Sachse, W.; Blake, D. R.; Bradshaw, J. D.; Kanakidou, M.; Crutzen, P. J. J. Geophys. Res. 1994, 99, 1805-1819
10. Andreae, M. O.; Merlet, P. Global Biogeochem. Cycles 2001, 15, 955-966
11. Talukdar, R. K.; Gierczak, T.; McCabe, D. C.; Ravishankara, A. R. J. Phys. Chem. A 2003, 107, 5021-5032
12. Wennberg, P. O.; Hanisco, T. F.; Jaeglé, L.; Jacob, D. J.; Hintsa, E. J.; Lanzendorf, E. J.; Anderson, J. G.; Gao, R. S.; Keim, E. R.; Donnelly, S. G. Science 1998, 279, 49-53
13. Yujing, M.; Mellouki, A. J. Photochem. Photobiol. 2000, 134, 31-36
14. Singh, H.; Chen, Y.; Staudt, A.; Jacob, D.; Blake, D.; Heikes, B.; Snow, J. Nature 2001, 410, 1078-1081
15. Blitz, M. A.; Heard, D. E.; Pilling, M. J. J. Phys. Chem. A 2006, 110, 6742-6756
16. Horowitz, A. J. Phys. Chem. 1991, 95, 10816-10823
17. Schulz, C.; Sick, V. Prog. Energy Combust. Sci. 2005, 31, 75-121
18. Hanson, R. K.; Seitzman, J. M.; Paul, P. H. Appl. Phys. B: Laser Opt. 1990, 50, 441-454
19. Einecke, S.; Schulz, C.; Sick, V. Appl. Phys. B: Laser Opt. 2000, 71, 717-723
20. Pepiot-Desjardins, P.; Pitsch, H.; Malhotra, R.; Kirby, S. R.; Boehman, A. L. Combust. Flame 2008, 154, 191-205
21. Hong, Z.; Davidson, D. F.; Vasu, S. S.; Hanson, R. K. Fuel 2009, 88, 1901-1906
22. Simmie, J. M. Prog. Energy Combust. Sci. 2003, 29, 599-634
23. Hassouna, M.; Delbos, E.; Devolder, P.; Viskolcz, B.; Fittschen, C. J. Phys. Chem. A 2006, 110, 6667-6672
24. Pichon, S.; Black, G.; Chaumeix, N.; Yahyaoui, M.; Simmie, J. M.; Curran, H. J.; Donohue, R. Combust. Flame 2009, 156, 494-504
25. El-Nahas, A. M.; Simmie, J. M.; Navarro, M. V.; Bozzelli, J. W.; Black, G.; Curran, H. J. Phys. Chem. Chem. Phys. 2008, 10, 7139-7149
26. Farkas, E.; Kovács, G.; Szilágyi, I.; Dóbé, S.; Bérces, T.; Márta, F. Int. J. Chem. Kinet. 2006, 38, 32-37
27. Delbos, E.; Devolder, P.; ElMaimouni, L.; Fittschen, C.; Brudnik, K.; Jodkowski, J. T.; Ratajczak, E. Phys. Chem. Chem. Phys. 2002, 4, 2941-2949
28. Imrik, K.; Farkas, E.; Vasvári, G.; Szilágyi, I.; Sarzyński, D.; Dóbé, S.; Bérces, T.; Márta, F. Phys. Chem. Chem. Phys. 2004, 6, 3958-3968
29. Serinyel, Z.; Chaumeix, N.; Black, G.; Simmie, J. M.; Curran, H. J. J. Phys. Chem. A 2010, 114, 12176-12186
30. Serinyel, Z.; Black, G.; Curran, H. J.; Simmie, J. M. Combust. Sci. Technol. 2010, 182, 574-587
31. Sebbar, N.; Bozzelli, J. W.; Bockhorn, H. Z. Phys. Chem. 2011, 225, 993-1018
32. Swalen, J. D.; Costain, C. C. J. Chem. Phys. 1959, 31, 1562-1574
33. Nguyen, H. V. L.; Stahl, W. ChemPhysChem 2011, 12, 1900-1905
34. Evangelisti, L.; Favero, L. B.; Maris, A.; Melandri, S.; Vega-Toribio, A.; Lesarri, A.; Caminati, W. J. Mol. Spectrosc. 2010, 259, 65-69
35. Pozdeev, N. M.; Mamleev, A. K.; Gunderova, L. N.; Galeev, R. V. J. Struct. Chem. 1988, 29, 52-58
36. El-Nahas, A. M.; Bozzelli, J. W.; Simmie, J. M.; Navarro, M. V.; Black, G.; Curran, H. J. J. Phys. Chem. A 2006, 110, 13618-13623
37. Bordwell, F. G.; Harrelson, J. A., Jr. Can. J. Chem. 1990, 68, 1714-1718
38. Bouchoux, G.; Chamot-Rooke, J.; Leblanc, D.; Mourgues, P.; Sablier, M. ChemPhysChem 2001, 2, 235-241
39. Cumming, J. B.; Kebarle, P. J. Am. Chem. Soc. 1977, 99, 5818-5820
40. Holmes, J. L.; Lossing, F. P.; Terlouw, J. K. J. Am. Chem. Soc. 1986, 108, 1086-1087
41. King, K. D.; Golden, D. M.; Benson, S. W. J. Am. Chem. Soc. 1970, 92, 5541-5546
42. Leroy, G.; Sana, M.; Wilante, C. J. Mol. Struct. (THEOCHEM) 1991, 228, 37-45
43. Reed, D. R.; Hare, M. C.; Fattahi, A.; Chung, G.; Gordon, M. S.; Kass, S. R. J. Am. Chem. Soc. 2003, 125, 4643-4651
44. Tsang, W. In Energetics of Stable Molecules and Reactive Intermediates; Minas da Piedade, M. E., Ed.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1999; Vol. 535, p 323.
45. Alnajjar, M. S.; Zhang, X. M.; Gleicher, G. J.; Truksa, S. V.; Franz, J. A. J. Org. Chem. 2002, 67, 9016-9022
46. Simmie, J. M.; Curran, H. J. J. Phys. Chem. A 2009, 113, 5128-5137
47. Ruscic, B.; Boggs, J. E.; Burcat, A.; Császár, A. G.; Demaison, J.; Janoschek, R.; Martin, J. M. L.; Morton, M. L.; Rossi, M. J.; Stanton, J. F. J. Phys. Chem. Ref. Data 2005, 34, 573-656
48. da Silva, G.; Bozzelli, J. W. J. Phys. Chem. A 2006, 110, 13058-13067
49. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
50. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789
51. Hudzik, J. M.; Asatryan, R.; Bozzelli, J. W. J. Phys. Chem. A 2010, 114, 9545-9553
52. Hudzik, J. M.; Bozzelli, J. W. J. Phys. Chem. A 2010, 114, 7984-7995
53. Curtiss, L. A.; Raghavachari, K.; Redfern, P. C.; Stefanov, B. B. J. Chem. Phys. 1998, 108, 692-697
54. Curtiss, L. A.; Raghavachari, K.; Redfern, P. C.; Rassolov, V.; Pople, J. A. J. Chem. Phys. 1998, 109, 7764-7776
55. Redfern, P. C.; Zapol, P.; Curtiss, L. A.; Raghavachari, K. J. Phys. Chem. A 2000, 104, 5850-5854
56. Baboul, A. G.; Curtiss, L. A.; Redfern, P. C.; Raghavachari, K. J. Chem. Phys. 1999, 110, 7650-7657
57. Curtiss, L. A.; Redfern, P. C.; Raghavachari, K.; Rassolov, V.; Pople, J. A. J. Chem. Phys. 1999, 110, 4703-4709
58. Montgomery, J. A., Jr.; Frisch, M. J.; Ochterski, J. W.; Petersson, G. A. J. Chem. Phys. 1999, 110, 2822-2827
59. Montgomery, J. A., Jr.; Frisch, M. J.; Ochterski, J. W.; Petersson, G. A. J. Chem. Phys. 2000, 112, 6532-6542
60. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; et al. Gaussian 03, revision D.01; Gaussian, Inc.: Wallingford, CT, 2003.
61. Chase, M. W., Jr. J. Phys. Chem. Ref. Data, Monogr. 1998, 9, 1-1951
62. Sheng, C. Ph.D. Dissertation, Department of Chemical Engineering, New Jersey Institute of Technology, Newark, NJ, 2002.
63. Pitzer, K. S. J. Chem. Phys. 1937, 5, 469-472
64. Pitzer, K. S. J. Chem. Phys. 1946, 14, 239-243
65. Pitzer, K. S.; Gwinn, W. D. J. Chem. Phys. 1942, 10, 428-440
66. Benson, S. W. Thermochemical Kinetics, 2 nd ed.; Wiley-Interscience: New York, 1976.
67. Lay, T. H.; Bozzelli, J. W.; Dean, A. M.; Ritter, E. R. J. Phys. Chem. 1995, 99, 14514-14527
68. Pedley, J. B. Thermochemical Data and Structures of Organic Compounds; Thermodynamics Research Center: College Station, TX, 1994.
69. Blanksby, S. J.; Ellison, G. B. Acc. Chem. Res. 2003, 36, 255-263
70. Chao, J.; Zwolinski, B. J. J. Phys. Chem. Ref. Data 1976, 5, 319-328
71. Buckley, E.; Herington, E. F. G. Trans. Faraday Soc. 1965, 61, 1618-1625
72. Cox, J. D.; Pilcher, G. Thermochemistry of Organic and Organometallic Compounds; Academic Press: New York, 1970.
73. Harrop, D.; Head, A. J.; Lewis, G. B. J. Chem. Thermodyn. 1970, 2, 203-210
74. Curtiss, L. A.; Raghavachari, K.; Redfern, P. C.; Pople, J. A. J. Chem. Phys. 2000, 112, 7374-7383
75. Luo, Y.-R. Comprehensive Handbook of Chemical Bond Energies; CRC Press: Boca Raton, FL, 2007.
76. Bauschlicher, C. W. Chem. Phys. Lett. 1995, 239, 252-257
77. Feng, Y.; Liu, L.; Wang, J. T.; Zhao, S. W.; Guo, Q. X. J. Org. Chem. 2004, 69, 3129-3138
78. Nickerson, J. K.; Kobe, K. A.; McKetta, J. J. J. Phys. Chem. 1961, 65, 1037-1043
79. Sinke, G. C.; Oetting, F. L. J. Phys. Chem. 1964, 68, 1354-1358
80. Goodman, L.; Gu, H.; Pophristic, V. J. Chem. Phys. 1999, 110, 4268-4275
81. Lowe, J. P. Science 1973, 179, 527-532
82. Kemp, J. D.; Pitzer, K. S. J. Chem. Phys. 1936, 4, 749-750
83. Mo, Y.; Gao, J. Acc. Chem. Res. 2007, 40, 113-119
84. Scott, A. P.; Radom, L. J. Phys. Chem. 1996, 100, 16502-16513
85. Stull, D. R.; Westrum, E. F., Jr.; Sinke, G. C. The Chemical Thermodynamics of Organic Compounds; Krieger Publishing Co.: Malibar, FL, 1987.
86. Pfaendtner, J.; Yu, X.; Broadbelt, L. J. Theor. Chem. Acc. 2007, 118, 881-898
87. Van Speybroeck, V.; Vansteenkiste, P.; Van Neck, D.; Waroquier, M. Chem. Phys. Lett. 2005, 402, 479-484
88. Van Speybroeck, V.; Van Neck, D.; Waroquier, M.; Wauters, S.; Saeys, M.; Marin, G. B. J. Phys. Chem. A 2000, 104, 10939-10950
89. Ayala, P. Y.; Schlegel, H. B. J. Chem. Phys. 1998, 108, 2314-2325
90. Vansteenkiste, P.; Van Neck, D.; Van Speybroeck, V.; Waroquier, M. J. Chem. Phys. 2006, 124, 044314
91. Lin, C. Y.; Izgorodina, E. I.; Coote, M. L. J. Phys. Chem. A 2008, 112, 1956-1964
92. Sharma, S.; Ramans, S.; Green, W. H. J. Phys. Chem. A 2010, 114, 5689-5701
93. Vansteenkiste, P.; Van Speybroeck, V.; Pauwels, E.; Waroquier, M. Chem. Phys. 2005, 314, 109-117
94. Tsang, W. In Energetics of Organic Free Radicals; Martinho Simões, J. A.; Greenberg, A.; Liebman, J. F., Eds.; Blackie Academic and Professional: London, 1996.
95. Solly, R. K.; Golden, D. M.; Benson, S. W. Int. J. Chem. Kinet. 1970, 2, 381-391
96. Tumanov, V. E.; Kromkin, E. A.; Denisov, E. T. Russ. Chem. Bull. 2002, 51, 1641-1650
97. Janoschek, R.; Rossi, M. J. Int. J. Chem. Kinet. 2004, 36, 661-686
98. Sellers, P. J. Chem. Thermodyn. 1970, 2, 211-219