Effects of sulfenyl, sulfinyl and sulfonyl groups on acidities and homolytic bond dissociation energies of adjacent C-H and N-H bonds

Journal of Physical Organic Chemistry

Volumn 11, Issue 6, 1998, Pages 397-406

  Bordwell, Frederick G ^a   Liu, Wei Zhong ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

Author keywords

Acidity; Bond dissociation energy; Phenylsulfenylamides; Phenylsulfenylanilides

Indexed keywords

EID: 0000401954     PISSN: 08943230     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-1395(199806)11:6<397::AID-POC10>3.0.CO;2-B     Document Type: Article

References (58)

1. (a)R. B. Bates and C. A. Ogle. Carbon Chemistry. Springer, New York (1983)
2. (b)F. M. Stoyanvich. in Chemistry of Organic Sulfur Compounds, edited by L. I. Belen'kii, Chapt. 6. Ellis Horwood, Chichester (1990)
3. (c)T. Hoz and H. Basch. in The Chemistry of Sulfur-Containing Functional Groups, edited by S. Patai, Z. Rappoport, Part A Chapt. 1. Wiley, Chichester (1993).
4. Y. Miura. Revi. Heteroatom Chem. 3, 211 (1990).
5. F. G. Bordwell. Acc. Chem. Res. 21, 456 (1988).
6. (a)F. G. Bordwell, M. J. Bausch, J. C. Branca and J. A. Harrelson. J. Phys. Org. Chem. 1, 225 (1988)
7. (b)F. G. Bordwell and X.-M. Zhang. J. Am. Chem. Soc. 116, 973 (1994)
8. (c)F. G. Bordwell, G. E. Drucker, N. H. Anderson and A. D. Denniston. J. Am. Chem. Soc. 108, 7310 (1986)
9. (d)M. S. Alnajjar, X.-M. Zhang, J. A. Franz and F. G. Bordwell. J. Org. Chem. 60, 4976 (1995)
10. (e)F. G. Bordwell, X.-M. Zhang and J.-P. Chen. J. Org. Chem. 56, 3216 (1991)
11. (f)F. G. Bordwell, J. A. Harrelson and T.-Y. Lynch. J. Org. Chem. 55, 3337 (1990).
12. K. Izutsu. Acid Base Dissociation Constants in Dipolar Aprotic Solvents, IUPAC Chemical Data Series, No. 35. Blackwell, Oxford (1990).
13. (a)D. F. McMillen and D. M. Golden. Anna. Rev. Phys. Chem. 33, 473 (1982)
14. (b)A. Jefferson, J. M. Nicovich and P. H. Wine. J. Phys. Chem. 98, 7128 (1994).
15. F. G. Bordwell, J.-P. Cheng, A. V. Satish and X.-M. Zhang. J. Am. Chem. Soc. 113, 9780 (1991).
16. F. G. Bordwell and J. A. Harrelson. Can. J. Chem. 68, 1714 (1990).
17. F. G. Bordwell, X.-M. Zhang and M. S. Alnajar. J. Am. Chem. Soc. 114, 7623 (1992).
18. (a)A. Streitwieser and J. E. Williams. J. Am. Chem. Soc. 97, 191 (1975)
19. (b)J. -M. Lehn and G. Wipff. J. Am. Chem. Soc. 98, 7498 (1976).
20. (a)S. Wolfe, L. A. Lajohn, F. Bernardi, A. Mangani and G. Tonachini. Tetrahedron Lett. 24, 3789 (1983)
21. (b)S. Wolfe, A. Stolow and L. A. Lajohn. Tetrahedron Lett. 24, 4071 (1983).
22. (a)K. B. Wiberg and H. Castejon. J. Am. Chem. Soc. 116, 10489 (1994)
23. (b)P. v. R. Schleyer, T. Clark, A. J. Kos, G. W. Spitznagel, C. Rohde, D. Arad, K. N. Houk and N. G. Rondan. J. Am. Chem. Soc. 106, 6467 (1984)
24. (c)P. v. R. Schleyer and A. J. Kos. Tetrahedron 39, 1141 (1983).
25. C. H. Patterson. J. Am. Chem. Soc. 111, 8059 (1989)
26. (c)P. Speers, K. E. Laidig and A Streitwiser. J. Am. Chem. Soc. 116, 9257 (1994).
27. S. H. Unger and C. Hansch. Prog. Phys. Org. Chem. 12, 91 (1976).
28. (a)C. Hansch, A. Leo and R. W. Taft. Chem. Rev. 91, 165 (1991);
29. (b)C. G. Swain and E. C. Lupton, Jr. J. Am. Chem. Soc. 90, 4328 (1968)
30. (c)H. C. Brown and Y. Okamoto. J. Am. Chem. Soc. 80, 4979 (1958)
31. (d)H. H. Jaffe. Chem. Rev. 53, 191 (1953)
32. (e)L. P. Hammett. J. Am. Chem. Soc. 59, 96 (1937).
33. (a)F. G. Bordwell and S. Zhang. J. Am. Chem. Soc. 117, 4858 (1995)
34. (b)F. G. Bordwell and X.-M. Zhang. J. Phys. Org. Chem. 8, 529 (1995)
35. (c)F. G. Bordwell and W. Liu. J. Am. Chem. Soc. 118, 10819 (1996).
36. (a)F. G. Bordwell, D. J. Algrim and J. A. Harrelson. J. Am. Chem. Soc. 110, 5903 (1988).
37. 18f
38. (e)W. K. Busfield, H. Mackle and P. A. G. O'Hare. Trans. Faraday Soc. 57, 1054; (1961); J. H. Mathews. J. Am. Chem. Soc. 48, 562 (1926).
39. (e)W. K. Busfield, H. Mackle and P. A. G. O'Hare. Trans. Faraday Soc. 57, 1054; (1961); J. H. Mathews. J. Am. Chem. Soc. 48, 562 (1926).
40. A. L. Allred. J. Inorg. Nucl. Chem. 17, 215 (1961).
41. H. Lumbroso and J. Cure. J. Mol. Struct. 98, 277 (1983).
42. F. G. Bordwell and W.-Z. Liu. J. Am. Chem. Soc. 118, 8777 (1996).
43. HAand BDE of adjacent CH and NH bonds for a PhO group are expected to be larger than the corresponding effect for a BzO group.
44. F. G. Bordwell, J. A. Harrelson and T.-Y. Lynch. J. Org. Chem. 55, 3337 (1990).
45. F. G. Bordwell, S. Zhang, X.-M. Zhang and W. Liu. J. Am. Chem. Soc. 117, 7092 (1995).
46. -) were found for several families of acids: (a)anilines: F. G. Bordwell, X.-M. Zhang and I.-P. Cheng. J. Org. Chem. 58, 6410 (1993); (b) triphenylmethanes: F. G. Bordwell, J.-P. Cheng, A. V. Satish and C. L. Twyman. J. Org. Chem. 57, 6542 (1992); (c) phenols: F. G. Bordwell and J.-P. Cheng. J. Am. Chem. Soc. 113, 1736 (1991).
47. -) were found for several families of acids: (a)anilines: F. G. Bordwell, X.-M. Zhang and I.-P. Cheng. J. Org. Chem. 58, 6410 (1993); (b) triphenylmethanes: F. G. Bordwell, J.-P. Cheng, A. V. Satish and C. L. Twyman. J. Org. Chem. 57, 6542 (1992); (c) phenols: F. G. Bordwell and J.-P. Cheng. J. Am. Chem. Soc. 113, 1736 (1991).
48. -) were found for several families of acids: (a)anilines: F. G. Bordwell, X.-M. Zhang and I.-P. Cheng. J. Org. Chem. 58, 6410 (1993); (b) triphenylmethanes: F. G. Bordwell, J.-P. Cheng, A. V. Satish and C. L. Twyman. J. Org. Chem. 57, 6542 (1992); (c) phenols: F. G. Bordwell and J.-P. Cheng. J. Am. Chem. Soc. 113, 1736 (1991).
49. J. P. Freeman. Org. Synth., Coll. Vol. 8, 550 (1993).
50. (a)F. G. Bordwell, J. E. Bares, J. E. Bartmess, G. J. McCollum, M. Van Der Puy, N. R. Vanier and W. S. Matthews. J. Org. Chem. 42, 321 (1977)
51. (b)F. G. Bordwell, J. E. Bares, J. E. Bartmess, G. E. Drucker, J. Gerhold, G. J. McCollum, M. Van Der Puy, N. R. Vanier and W. S. Matthews. J. Org. Chem. 42, 326 (1977).
52. Y. Miura and M. Kinoshita. Bull. Chem. Soc. Jpn. 50, 1142 (1977).
53. P. Brownbridge. Tetrahedron Lett. 25, 3759 (1984).
54. V. G. Boldyrev and S. A. Kolesnikova. Zh. Org. Khim. 5, 1088 (1968).
55. H. Gilman and H. L. Morris. J. Am. Chem. Soc. 48, 2399 (1926).
56. M. Ludwig, O. Pytela, H. Javurkova and M. Vecera. Collect. Czech. Chem. Commun. 52, 2900 (1987).
57. (a)W. S. Matthews, J. E. Bares, J. E. Bartmess, F. G. Bordwell, F. J. Cornforth, G. E. Drucker, Z. Margolin, R. J. McCallum, G. J. McCollum and N. R. Vanier. J. Am. Chem. Soc. 97, 7006 (1975);
58. (b)W. N. Olmstesd, Z. Margolin and F. G. Bordwell. J. Org. Chem. 45, 3295 (1980).