An intrinsic radical stability scale from the perspective of bond dissociation enthalpies: A companion to radical electrophilicities

Journal of Organic Chemistry

Volumn 73, Issue 22, 2008, Pages 9109-9120

  De Vleeschouwer, Freija ^a   Van Speybroeck, Veronique ^b   Waroquier, Michel ^b   Geerlings, Paul ^a   De Proft, Frank ^a  

^a VRIJE UNIVERSITEIT BRUSSEL   (Belgium)

^b GHENT UNIVERSITY   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

ATOMIC PHYSICS; ATOMS; CHEMICAL BONDS; DENSITY FUNCTIONAL THEORY; DISSOCIATION; ENTHALPY; FLUORINE; HYDROGEN; KETONES; METHANOL; RANGE FINDING; REACTION KINETICS; SYSTEM STABILITY;

BOND DISSOCIATION ENTHALPIES; CHEMICAL CONCEPTS; ELECTROPHILICITY; EXPERIMENTAL VALUES; FLUORINE ATOMS; HYDROXYMETHYL RADICALS; INTRINSIC STABILITIES; MEAN ABSOLUTE DEVIATIONS; NEUTRAL HYDROGENS; RADICAL SYSTEMS; SPIN DENSITIES;

CHEMICAL STABILITY;

FLUORINE; GLYCEROL; HYDROGEN; HYDROXIDE; METHYL GROUP;

ARTICLE; CHEMICAL BOND; CHEMICAL MODEL; DENSITY FUNCTIONAL THEORY; DISSOCIATION; ENTHALPY;

EID: 56449115941     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo802018b     Document Type: Article

References (78)

1. Blanksby, S. J.; Ellison, G. B. Acc. Chem. Res. 2003, 36, 255-263.
2. Berkowitz, J.; Ellison, G. B.; Gutman, D. J. Phys. Chem. 1994, 98, 2744-2765.
3. Lide, D. R. CRC Handbook of Chemistry and Physics; CRC Press LLC: Florida, 2002.
4. Cherkasov, A.; Jonsson, M. J. Chem. Inf. Comput. Sci. 2000, 40, 1222-1226.
5. Urata, S.; Takada, A.; Uchimaru, T.; Chandra, A. K.; Sekiya, A. J. Fluorine Chem. 2002, 116, 163-171.
6. Luo, Y. R. Int. J. Chem. Kinet. 2002, 34, 453-466.
7. Bosque, R.; Sales, J. J. Chem. Inf. Comput. Sci. 2003, 43, 637-642.
8. Jursic, B. S. J. Chem. Soc., Perkin Trans. 2 1999, 369-372.
9. Zhang, H. Y.; Chen, D. Z. Chin. J. Org. Chem. 2001, 21, 66-70.
10. Sun, Y. M.; Zhang, H. Y.; Chen, D. Z. Chin. J. Chem. 2001, 19, 657-661.
11. DiLabio, G. A.; Pratt, D. A.; Lofaro, A. D.; Wright, J. S. J. Phys. Chem. A 1999, 103, 1653-1661.
12. DiLabio, G. A.; Pratt, D. A. J. Phys. Chem. A 2000, 104, 1938-1943.
13. Johnson, E. R.; Clarkin, O. J.; DiLabio, G. A. J. Phys. Chem. A 2003, 107, 9953-9963.
14. Yao, X. Q.; Hou, X. J.; Jiao, H. J.; Xiang, H. W.; Li, Y. W. J. Phys. Chem. A 2003, 107, 9991-9996.
15. Feng, Y.; Liu, L.; Wang, J. T.; Huang, H.; Guo, Q. X. J. Chem. Inf. Comput. Sci. 2003, 43, 2005-2013.
16. Qi, X. J.; Feng, Y.; Liu, L.; Guo, Q. X. Chin. J. Chem. 2005, 23, 194-199.
17. Pople, J. A.; Head Gordon, M.; Raghavachari, K. J. Chem. Phys. 1987, 87, 5968-5975.
18. Scuseria, G. E.; Schaefer, H. F. J. Chem. Phys. 1989, 90, 3700-3703.
19. Curtiss, L. A.; Raghavachari, K.; Trucks, G. W.; Pople, J. A. J. Chem. Phys. 1991, 94, 7221-7230.
20. Curtiss, L. A.; Raghavachari, K.; Redfern, P. C.; Rassolov, V.; Pople, J. A. J. Chem. Phys. 1998, 109, 7764-7776.
21. Boese, A. D.; Oren, M.; Atasoylu, O.; Martin, J. M. L.; Kallay, M.; Gauss, J. J. Chem. Phys. 2004, 120, 4129-4141, and references therein.
22. Karton, A.; Rabinovich, E.; Martin, J. M. L.; Ruscic, B. J. Chem. Phys. 2006, 125.
23. Izgorodina, E. I.; Coote, M. L.; Radom, L. J. Phys. Chem. A 2005, 109, 7558-7566.
24. Zhao, Y.; Truhlar, D. G. J. Phys. Chem. A 2008, 112, 1095-1099.
25. Hemelsoet, K.; Van Speybroeck, V.; Waroquier, M. J. Phys. Chem., in press.
26. Senosiain, J. P.; Han, J. H.; Musgrave, C. B.; Golden, D. M. Faraday Discuss. 2001, 119, 173-189.
27. Politzer, P.; Murray, J. S.; Lane, P.; Toro-Labbe, A. Int. J. Quantum Chem. 2007, 107, 2153-2157.
28. Mo, O.; Yanez, M.; Eckert-Maksic, M.; Maksic, Z. B.; Alkorta, I.; Elguero, J. J. Phys. Chem. A 2005, 109, 4359-4365.
29. Coote, M. L.; Pross, A.; Radom, L. Org. Lett. 2003, 5, 4689-4692.
30. Parkinson, C. J.; Mayer, P. M.; Radom, L. Theor. Chem. Acc. 1999, 102, 92-96.
31. Henry, D. J.; Parkinson, C. J.; Mayer, P. M.; Radom, L. J. Phys. Chem. A 2001, 105, 6750-6756.
32. Menon, S.; Wood, G. P. F.; Moran, D.; Radom, L. J. Phys. Chem. A 2007, 111, 13638-13644.
33. Wood, G. P. F.; Moran, D.; Jacob, R.; Radom, L. J. Phys. Chem. A 2005, 109, 6318-6325.
34. Finkelshtein, E. I. J. Phys. Org. Chem. 2001, 14, 543-550.
35. Wayner, D. D. M.; Clark, K. B.; Rauk, A.; Yu, D.; Armstrong, D. A. J. Am. Chem. Soc. 1997, 119, 8925-8932.
36. Matsunaga, N.; Rogers, D. W.; Zavitsas, A. A. J. Org. Chem. 2003, 68, 3158-3172.
37. Parr, R. G.; Yang, W. T. Density Functional Theory of Atoms and Molecules; Oxford University Press: New York, 1989.
38. Parr, R. G.; Yang, W. T. Annu. Rev. Phys. Chem. 1995, 46, 701-728.
39. Geerlings, P.; De Proft, F.; Langenaeker, W. Adv. Quantum Chem. 1999, 33, 303.
40. Chermette, H. J. Comput. Chem. 1999, 20, 129-154.
41. Geerlings, P.; De Proft, F.; Langenaeker, W. Chem. Rev. 2003, 103, 1793-1873.
42. Ayers, P. W.; Anderson, J. S. M.; Bartolotti, L. J. Int. J. Quantum Chem. 2005, 101, 520-534.
43. Parr, R. G.; Donnelly, R. A.; Levy, M.; Palke, W. E. J. Chem. Phys. 1978, 68, 3801-3807.
44. Parr, R. G.; Von Szentpaly, L.; Liu, S. B. J. Am. Chem. Soc. 1999, 121, 1922-1924.
45. Huheey, J. E.; Keiter, E. A.; Keiter, R. L. Inorganic Chemistry: Principles of Structure and Reactivity; Harper Collins College Publishers: New York, 1993.
46. Parr, R. G.; Yang, W. T. Density Functional Theory of Atoms and Molecules; Oxford University Press: New York, 1989; Vol. 90, p 95.
47. De Vleeschouwer, F.; Van Speybroeck, V.; Waroquier, M.; Geerlings, P.; De Proft, F. Org. Lett. 2007, 9, 2721-2724.
48. Van Speybroeck, V.; Marin, G. B.; Waroquier, M. ChemPhysChem 2006, 7, 2205-2214.
49. Pratt, D. A.; Wright, J. S.; Ingold, K. U. J. Am. Chem. Soc. 1999, 121, 4877-4882.
50. Fu, Y.; Yu, T. Q.; Wang, Y. M.; Liu, L.; Guo, Q. X. Chin. J. Chem. 2006, 24, 299-306.
51. Geerlings, P.; De Proft, F. Phys. Chem. Chem. Phys. 2008, 10, 3028.
52. Chattaraj, P. K.; Sarkar, U.; Roy, D. R. Chem. Rev. 2006, 106, 2065-2091.
53. Parr, R. G.; Pearson, R. G. J. Am. Chem. Soc. 1983, 105, 7512-7516.
54. Gronert, S. J. Org. Chem. 2006, 71, 1209-1219.
55. Pauling, L. J. Am. Chem. Soc. 1932, 54, 3570-3582.
56. Pauling, L. The Nature of the Chemical Bond and the Structures of Molecules and Crystals, 3rd ed.; Cornell University Press: Ithaca, NY, 1960.
57. Ochterski, J. W.; Petersson, G. A.; Wiberg, K. B. J. Am. Chem. Soc. 1995, 117, 11299-11308.
58. Pitzer, K. S. J. Chem. Phys. 1955, 23, 1735.
59. Mulliken, R. S. J. Am. Chem. Soc. 1955, 77, 884-887.
60. Caldow, G. L.; Coulson, C. A. Trans. Faraday Soc. 1962, 58, 633.
61. Jolly, W. L.; Eyermann, C. J. Inorg. Chem. 1983, 22, 1566.
62. Forslund, L. E.; Kaltsoyannis, N. New J. Chem. 2003, 27, 1108-1114.
63. Mckee, M. L. J. Am. Chem. Soc. 1995, 117, 1629-1637.
64. Olson, L. P.; Kuwata, K. T.; Bartberger, M. D.; Houk, K. N. J. Am. Chem. Soc. 2002, 124, 9469-9475.
65. Singh, N. K.; Popelier, P. L. A.; O'Malley, P. J. Chem. Phys. Lett. 2006, 426, 219-221.
66. Dust, J. M.; Arnold, D. R. J. Am. Chem. Soc. 1983, 105, 1221-1227.
67. Wiberg, K. B.; Hadad, C. M.; Rablen, P. R.; Cioslowski, J. J. Am. Chem. Soc. 1992, 114, 8644-8654.
68. Clayden, J.; Greeves, N.; Warren, S.; Wothers, P. Organic Chemistry; Oxford University Press: Oxford, 2001.
69. Coote, M. L.; Dickerson, A. B. Aust. J. Chem. 2008, 61, 163-167.
70. Frisch, J. A. Gaussian 03, revision B.03; Gaussian, Inc.: Wallinford, CT, 2004.
71. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
72. Lee, C. T.; Yang, W. T.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
73. Hehre, W. J. Acc. Chem. Res. 1976, 9, 399-406.
74. Perdew, J. P. Phys. Rev. B 1986, 33, 8822-8824.
75. Boese, A. D.; Martin, J. M. L. J. Chem. Phys. 2004, 121, 3405-3416.
76. Reed, A. E.; Weinhold, F. J. Chem. Phys. 1985, 83, 1736-1740.
77. Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735-746.
78. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899-926.