On the advantages of hydrocarbon radical stabilization energies based on R-H bond dissociation energies

Journal of Organic Chemistry

Volumn 76, Issue 8, 2011, Pages 2439-2447

  Wodrich, Matthew D ^a   McKee, W Chad ^b   Schleyer, Paul Von Ragué ^b  

^a UNIVERSITY OF GENEVA   (Switzerland)

^b UNIVERSITY OF GEORGIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTRONEGATIVITY DIFFERENCE; H-BONDS; HYDROCARBON RADICALS; HYPERCONJUGATION; INTRAMOLECULAR INTERACTIONS; REFERENCE SYSTEMS; STERIC CROWDING;

CHEMICAL BONDS; DISSOCIATION; ELECTRONEGATIVITY; FREE RADICALS; STABILIZATION;

HYDROCARBONS;

HYDROCARBON;

ARTICLE; CONJUGATION; ENERGY; HYDROGEN BOND; MOLECULAR INTERACTION; MOLECULAR STABILITY; RADICAL REACTION; RADICAL STABILIZATION ENERGY; STEREOSPECIFICITY;

EID: 79953899825     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo101661c     Document Type: Article

References (77)

1. Zavitsas, A. A.; Rogers, D. W.; Matsunaga, N. J. Org. Chem. 2010, 75, 5697
2. Exner, K.; Schleyer, P. v. R. J. Phys. Chem. A 2001, 105, 3407
3. Berkowitz, J.; Ellison, G. B.; Gutman, D. J. Phys. Chem. 1994, 98, 2744
4. Yao, X.-Q.; Hou, X.-J.; Jiao, H.; Xiang, H.-W.; Li, Y.-W. J. Phys. Chem. A 2003, 107, 9991
5. Johnson, E. R.; Clarkin, O. J.; DiLabio, G. A. J. Phys. Chem. A 2003, 107, 9953
6. Feng, Y.; Liu, L.; Wang, J.-T.; Huang, H.; Guo, Q.-X. J. Chem. Inf. Comput. Sci. 2003, 43, 2005
7. Izgorodina, E. I.; Coote, M. L.; Radom, L. J. Phys. Chem. A 2005, 109, 7558
8. Agapito, F.; Nunes, P. M.; Cabral, B. J. C.; dos Santos, R. M. B.; Simoes, J. A. M. J. Org. Chem. 2007, 72, 8770
9. Nunes, P. M.; Estacio, S. G.; Lopes, G. T.; Cabral, B. J. C.; dos Santos, R. M. B.; Simoes, J. A. M. Org. Lett. 2008, 10, 1613
10. Hemelsoet, K.; van Speybroeck, V.; Waroquier, M. J. Phys. Chem. A 2008, 112, 13566
11. van Zeist, W.-J.; Bickelhaupt, F. M. Phys. Chem. Chem. Phys. 2009, 11, 10317
12. Zhang, I. Y.; Wu, J.; Luo, Y.; Xu, X. J. Chem. Theory Comput. 2010, 6, 1462
13. Luo, Y.-R. Handbook of Bond Dissociation Energies; CRC Press: New York, 2003.
14. Cox, R. D.; Pilcher, G. Thermochemistry of Organic and Organometallic Compounds; Academic Press: New York, 1970.
15. Pedley, J. B.; Naylor, R. D.; Kirby, S. P. Thermochemical Data of Organic Compounds; Chapman and Hall: London, 1986.
16. Cohen, N. J. Phys. Chem. Ref. Data 1996, 25, 1411
17. Matsunaga, N.; Rogers, D. W.; Zavitsas, A. A. J. Org. Chem. 2003, 68, 3158
18. Zavitsas, A. A. J. Org. Chem. 2008, 73, 9022
19. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; John Wiley & Sons: New York, 1986.
20. Parkinson, C. J.; Mayer, P. M.; Radom, L. Theor. Chem. Acc. 1999, 102, 92
21. Parkinson, C. J.; Mayer, P. M.; Radom, L. J. Chem. Soc., Perkin Trans. 2 1999, 11, 2305
22. Henry, D. J.; Parkinson, C. J.; Mayer, P. M.; Radom, L. J. Phys. Chem. A 2001, 105, 6750
23. Campos, L. M.; Dang, H.; Ng, D.; Yang, Z.; Martinez, H. L.; Garcia-Garibay, M. A. J. Org. Chem. 2002, 67, 3749
24. Menon, A. S.; Radom, L. J. Phys. Chem. A 2008, 112, 13225
25. Goerigk, L.; Grimme, S. J. Chem. Theory Comput. 2010, 6, 107
26. Poutsma, M. L. J. Org. Chem. 2008, 73, 8921
27. Blanksby, S. J.; Ellison, G. B. Acc. Chem. Res. 2003, 36, 255
28. Mo, Y. J. Org. Chem. 2010, 75, 2733
29. Wertz, J. E.; Bolton, J. R. Electron Spin Resonance, Elementary Theory and Practical Applications, 2 nd ed.; J. Wiley & Sons: New York, 2007.
30. Mo, Y.; Hiberty, P. C.; Schleyer, P. v. R. Theor. Chem. Acc. 2010, 127, 27
31. Coote, M. L.; Pross, A.; Radom, L. Org. Lett. 2003, 5, 4689
32. Rüchardt, C. Angew. Chem., Int. Ed. 1970, 9, 830
33. Coote, M. L.; Lin, C. Y.; Beckwith, A. L. J.; Zavitsas, A. A. Phys. Chem. Chem. Phys. 2010, 12, 9597
34. Poutsma, M. L. J. Org. Chem. 2011, 76, 270
35. Pauling, L. J. Am. Chem. Soc. 1932, 54, 3570
36. Pauling, L. C. The Nature of the Chemical Bond, 3 rd ed.; Cornell University Press: Ithaca, 1960.
37. Pauling values are given as 2.5 or 2.55 for C and 2.1 or 2.2 for H in various textbooks. See ref 34.
38. 3) Mulliken-Jaffé; H, 2.300; C, 2.544. Allen gave even smaller C,H difference. See ref 58.
39. Signorell, R.; Marquardt, R.; Quack, M.; Suhm, M. A. Mol. Phys. 1996, 89, 297
40. Hollenstein, H.; Marquardt, R.; Quack, M.; Suhm, M. A. J. Chem. Phys. 1994, 101, 3588
41. Huheey, J. E. J. Phys. Chem. 1965, 69, 3284
42. Cao, C.; Luo, J. QSAR Comb. Sci. 2007, 26, 955
43. NIST Computational Chemistry Comparison and Benchmark Database, NIST Standard Reference Database Number 101 Release 15a, April 2010; R. D. Johnson III, Ed.; http://cccbdb.nist.gov/.
44. Afeefy, H. Y.; Liebman, J. F.; Stein, S. E. Neutral Thermochemical Data. In NIST Chemistry WebBook, NIST Standard Reference Database Number 69; Linstrom, P. J.; Mallard, W. G., Eds.; National Institute of Standards and Technology: Gaithersburg, MD, 2004; http://webbook.nist.gov/.
45. ZRM derived a value of 1.1 kcal/mol for this equation using different experimental data. We employ NIST values.
46. Wodrich, M. D.; Wannere, C. S.; Mo, Y.; Jarowski, P. D.; Houk, K. N.; Schleyer, P. v. R. Chem. - Eur. J. 2007, 13, 7731
47. Wodrich, M. D.; Schleyer, P. v. R. Org. Lett. 2006, 8, 2135
48. Wodrich, M. D.; Corminboeuf, C.; Schleyer, P. v. R. Org. Lett. 2006, 8, 3631
49. Wodrich, M. D.; Jana, D. F.; Schleyer, P. v. R.; Corminboeuf, C. J. Phys. Chem. A 2008, 112, 11495
50. Estrada, E. Chem. Phys. Lett. 2008, 463, 422
51. Kemnitz, C. R.; Mackey, J. L.; Loewen, M. J.; Hargrove, J. L.; Lewis, J. L.; Hawkins, W. E.; Nielsen, A. F. Chem. - Eur. J. 2010, 16, 6942
52. Schleyer, P. v. R.; McKee, W. C. J. Phys. Chem. A 2010, 114, 3737
53. Gonthier, J. F.; Wodrich, M. D.; Steinmann, S. N.; Corminboeuf, C. Org. Lett. 2010, 12, 3070
54. Ess, D. H.; Liu, S.; De Proft, F. J. Phys. Chem. A 2010, 114, 12952
55. We will discuss the origins of protobranching in a forthcoming paper. Note the increasing support for this concept, e.g., in refs 25, 29, and 48-52, and Wodrich, M. D.; Corminboeuf, C.; Schreiner, P. R.; Fokin, A. A.; Schleyer, P. v. R. Org. Lett. 2007, 9, 1851
56. For critical views, see: Gronert, S. Chem. - Eur. J. 2009, 15, 5372
57. Fishtik, I. J. Phys. Chem. A 2010, 114, 3731
58. Cohen, N.; Benson, S. W. Chem. Rev. 1993, 93, 2419
59. Bastianson, O.; Samdal, S. J. Mol. Struct. 1985, 128, 115
60. Mo, Y.; Peyerimhoff, S. D. J. Chem. Phys. 1998, 109, 1687
61. Mulliken, R. S. J. Chem. Phys. 1939, 7, 339
62. Mulliken, R. S.; Rieke, C. A.; Brown, W. G. J. Am. Chem. Soc. 1941, 63, 41
63. Gibson, J. F.; Ingram, D. J. E.; Symons, M. C. R.; Townsend, M. G. Trans. Faraday Soc. 1957, 53, 914
64. Muller, N.; Mulliken, R. S. J. Am. Chem. Soc. 1958, 80, 3489
65. Mulliken, R. S. Tetrahedron 1959, 5, 253
66. Mulliken, R. S. Tetrahedron 1959, 6, 68
67. Symons, M. C. R. Tetrahedron 1962, 18, 333
68. Mo, Y.; Gao, J. L.; Peyerimhoff, S. D. J. Chem. Phys. 2000, 112, 5530
69. Wu, W.; Ma, B.; Wu, J. I.-C.; Schleyer, P. v. R.; Mo, Y. Chem. - Eur. J. 2009, 15, 9730
70. Mo, Y.; Gao, J. Acc. Chem. Res. 2007, 40, 113
71. Weinhold, F.; Landis, C. Valency and Bonding, A Natural Bond Orbital Donor-Acceptor Perspective, 1 st ed.; Cambridge University Press: Cambridge, 2005.
72. Song, L.; Mo, Y.; Zhang, Q.; Wu, W. J. Comput. Chem. 2005, 26, 514
73. Goodman, L.; Phophristic, V. Nature 2001, 411, 565
74. Weinhold, F. Nature 2001, 411, 539
75. Weinhold, F. Angew. Chem., Int. Ed. 2003, 42, 4188
76. Badenhoop, J. K.; Weinhold, F. Int. J. Quantum Chem. 1999, 72, 269
77. Bickelhaupt, F. M.; Baerends, E. J. Angew. Chem., Int. Ed. 2003, 42, 4183