Role of polar and enthalpic effects in the addition of methyl radical to substituted alkenes: A density functional study including solvent effects

Journal of the American Chemical Society

Volumn 120, Issue 23, 1998, Pages 5733-5740

  Arnaud, Roger ^a   Bugaud, Nicolas ^a   Vetere, Valentina ^b   Barone, Vincenzo ^b  

^a UNIVERSITÉ JOSEPH FOURIER   (France)

^b UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; METHYL GROUP; SOLVENT;

ARTICLE; CALCULATION; DENSITY; ELECTRON; ENERGY; ENTHALPY; MODEL;

EID: 84961979062     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja973896p     Document Type: Article

References (55)

1. Tedder, J. M. Angew. Chem., Int. Ed. Engl. 1982, 21, 401.
2. Giese, B. Angew. Chem., Int. Ed. Engl. 1983, 22, 753.
3. Von Sonntag, C. The Chemical Basis of Radiation Biology; Taylor & Francis: London, 1987; Chapter 6.
4. Hoganson, W.; Babcock, G. T. Biochemistry 1992, 31, 11874.
5. Heberger, K.; Fischer, H. Int. J. Chem. Kinet. 1993, 113, 4324.
6. (a) Zytowski, T.; Fischer, H. J. Am. Chem. Soc. 1996, 118, 437.
7. (b) Fischer, H. In Free Radicals in Biology and Environment, Minisci, F., Ed.; Kluwer: Dordrecht, 1997; p 69.
8. (c) Zytowski, T.; Fischer, H. J. Am. Chem. Soc. 1997, 119, 12869.
9. (a) Wong, M. W.; Pross, A.; Radom, L. J. Am. Chem. Soc. 1993, 115, 11050.
10. (b) Ibid. 1994, 116, 6284.
11. For an assessment of ab initio procedures, see: (a) Wong, M. W.; Radom, L. J. Phys. Chem. 1995, 99, 8582. (b) Heuts, J. P. A.; Gilbert, R. G.; Radom, L. J. Phys. Chem. 1996, 100, 18997.
12. For an assessment of ab initio procedures, see: (a) Wong, M. W.; Radom, L. J. Phys. Chem. 1995, 99, 8582. (b) Heuts, J. P. A.; Gilbert, R. G.; Radom, L. J. Phys. Chem. 1996, 100, 18997.
13. Parr, R. G.; Yang, W. Density-Functional Theory of Atoms and Molecules; Oxford University Press: New York, 1989.
14. Becke, A. D. J. Chem. Phys. 1993, 98, 1372.
15. Barone, V.; Adamo, C. Chem. Phys. Lett. 1994, 224, 432; erratum 1994, 228, 499.
16. Barone, V. J. Chem. Phys. 1994, 101, 10666.
17. Barone, V. In Advances in Density Functional Methods, part I; Chong, D. P., Ed.; World Scientific Publishing Co.: Singapore, 1995; Chapter 8, p 278.
18. Baker, J.; Muir, M.; Andzelm, J. Chem. Phys. 1995, 102, 2063.
19. (a) Barone, V.; Orlandini, L. Chem. Phys. Lett. 1995, 246, 45.
20. (b) Bottoni, A. J. Chem. Soc., Perkin Trans. 2 1996, 2041.
21. (c) Jursic, B.S. J. Chem. Soc., Perkin Trans. 2 1997, 637.
22. Cossi, M.; Barone, V.; Cammi, R.; Tomasi, J. Chem. Phys. Lett. 1996, 255, 327.
23. Barone, V.; Cossi, M.; Tomasi, J. J. Comput.Chem. 1998, 19, 407.
24. Miertùs, S.; Scrocco, E.; Tomasi, J. Chem. Phys. 1981, 55, 117.
25. Gaussian 94 (Revision D.4): M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. A. Keith, G. A. Petersson, J. A. Montgomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakrewski, J. V. Ortiz, J. B. Foresman, B. Cioslowski, B. Stefanov, A. Nanayakkara, M. Challacombe, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. P. Stewart, M. Head-Gordon, C. Gonzalez, J. A. Pople, Gaussian Inc., Pittsburgh, PA, 1995.
26. Rega, N.; Cossi, M.; Barone, V. J. Chem. Phys. 1996, 105, 11060.
27. Rega, N.; Cossi, M.; Barone, V. J. Am. Chem. Soc. 1997, 119, 12962.
28. Viehe, H. G.; Janousek, Z.; Merényi, R.; Stella, L. Acc. Chem. Res. 1985, 18, 148.
29. Becke, A.D. Phys. Rev. 1988, 38, 3098.
30. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
31. Becke, A. D. J. Chem. Phys. 1993, 95, 5648.
32. Description of basis sets and explanation of standard levels of theory can be found in the following: Foresman, J. B.; Frisch, A. E. Exploring Chemistry with Electronic Structure Methods, 2nd ed.; Gaussian, Inc.: Pittsburgh, PA, 1996.
33. Boys, S.; Bernardi, F. Mol. Phys. 1970, 19, 553.
34. Eyring, H.; Liu, S. H.; Liu, S. M. Basic Chemical Kinetics; Wiley: New York, 1980.
35. Arnaud, R.; Subra, R.; Barone, V.; Lelj, F.; Olivella, S.; Sole, A.; Russo, N. J. Chem. Soc., Perkin Trans. 2 1986, 1517.
36. We thank Prof. H. Fischer and Dr. T. Zytowski (University of Zurich) for kindly performing this measurement.
37. Barone, V.; Cossi, M.; Tomasi, J. J. Chem. Phys. 1997, 107, 3210.
38. Curtiss, L. A.; Pochatko, D. J.; Reed, A. E.; Weinhold, F. J. Chem. Phys. 1983, 82, 2679.
39. Tyrell, J.; Weinstock, R. B.; Weinhold, F. Int. J. Quantum Chem. 1981, 19, 781.
40. (a) Truhlar, D. G.; Garrett, B. C. Annu. Rev. Phys. Chem. 1984, 35, 159.
41. (b) Tucker, S.; Truhlar, D. G. In New Theoretical Concepts for Understanding Organic Reactions; Bertran, J., Csizmadia, I., Eds.; Kluwer: Dordrecht, 1989; p 291.
42. (c) Truhlar, D. G. J. Chem. Soc., Faraday Trans. 1994, 90, 1740.
43. Minichino, C.; Barone, V. J. Chem. Phys. 1994, 100, 3717.
44. (b) Barone, V.; Minichino, C. Theochem 1995, 330, 365.
45. Truhlar, D. G.; Garrett, B. C. Acc. Chem. Res. 1980, 13, 440.
46. (a) Barone, V.; Arnaud, R., J. Chem. Phys. 1997, 106, 8727.
47. (b) Arnaud, R.; Vetere, V.; Barone, V. Manuscript in preparation.
48. Wu, J. Q.; Fischer, H. Int. J. Chem. Kinet. 1995, 27, 167.
49. (a) Pasto, D. J. J. Am. Chem. Soc. 1988, 110, 8164.
50. (b) Leroy, G.; Sana, M.; Wilante, C. J. Mol. Struct.: THEOCHEM 1991, 234, 303.
51. (c) Espinosa-Garcia, J.; Olivares del Valle, F. J.; Leroy, G.; Sana, M. J. Mol. Struct.: THEOCHEM 1992, 258, 315.
52. (d) Davidson, E. R.; Chakravorty, S.; Gajewski, J. J. New J. Chem. 1997, 21, 533.
53. Villa, J.; Gonzalez-Lafont, A.; Lluch, J. M.; Corchado, J. C.; Espinosa-Garcia, J. J. Chem. Phys. 1997, 107, 7266.
54. Mayer, P. M.; Parkinson, C. J.; Smith, D. M.; Radom, L. J. Chem. Phys. 1998, 108, 604.
55. Jencks, W. P. Chem. Rev. 1985, 85, 5111 and references therein.