Mechanism of 5,5-dimethylhydantoin chlorination: Monochlorination through a dichloro intermediate

Journal of Chemical Theory and Computation

Volumn 3, Issue 6, 2007, Pages 2282-2289

  Akdag, Akin ^a   Worley, S D ^a   Acevedo, Orlando ^a   McKee, Michael L ^a  

^a AUBURN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 36649015367     PISSN: 15499618     EISSN: None     Source Type: Journal    
DOI: 10.1021/ct7001804     Document Type: Article

References (52)

1. Avendaño, C.; Menendez, J. C. Hydantoin and Its Derivatives In Kirk-Othmer Encyclopedia Chemical Technology, 4th ed.; 2000; pp 1-21. (DOI:10.1002/ 0471238961.0825040101220514.a01).
2. Meusel, M.; Gütschow, M. Org. Preparations Procedures Int. 2004, 36, 391-443.
3. (a) Kruger, H. G.; Mdluli, P. S. Struct. Chem. 2006, 17, 121-125.
4. (b) Teng, X.; Degterev, A.; Jagtap, P.; Xing, X.; Choi, S.; Denu, R.; Yuan, J.; Cuny, G. D. Bioorg. Med. Chem. Lett. 2005, 15, 5039-5044.
5. (c) Riley, P.; Figary, P. C.; Entwisle, J. R.; Roe, A. L.; Thompson, G. A.; Ohashi, R.; Ohashi, N.; Moorehead, T. J. J. Pharm. Sci. 2005, 94, 2084-2095.
6. (d) Wehner, V.; Stilz, H.-U.; Osipov, S. N.; Golubev, A. S.; Sieler, J.; Burger, K. Tetrahedron 2004, 60, 4295-4302.
7. (e) Bakalova, A.; Buyukliev, R.; Momekov, G.; Ivanov, D.; Todorov, D.; Konstantinov, S.; Karaivanova, M. Eur. J. Med. Chem. 2005, 40, 590-596.
8. (f) Krishnan, R. S. G.; Thennarasu, S.; Mandal, A. B. Chem. Phys. 2003, 291, 195-205.
9. (a) Akdag, A.; Webb, T.; Worley, S. D. Tetrahedron Lett. 2006, 47, 3509-3510.
10. (b) Walters, T. R.; Zajac, W. W.; Woods, J. M. J. Org. Chem. 1991, 56, 316-321.
11. (c) Szumigala, R. H.; Devine, P. N.; Gauthier, D. R.; Volante, R. P. J. Org. Chem. 2004, 69, 566-569.
12. (d) Rivera, N. R.; Balsells, J.; Hansen, K. B. Tetrahedron Lett. 2006, 47, 4889-4891.
13. (e) Bartoli, G.; Bosco, M.; Carlone, A.; Locatelli, M.; Melchiorre, P.; Sambri, L. Angew. Chem., Int. Ed. 2005, 44, 6219-6222.
14. (f) Soracco, R. J.; Wilde, E. W.; Mayack, L. A.; Pope, D. H. Water Res. 1985, 19, 763-766.
15. (g) Koval, I. V. Russ. J. Org. Chem. 2001, 37, 297-317.
16. (a) Tsao, T. C.; Williams, D. E.; Worley, C. G.; Worley, S. D. Biotechnol. Prog. 1991, 7, 60-66.
17. (b) Chen, Y.; Worley, S. D.; Kim, J.; Wei, C.-I.; Chen, T.-Y.; Suess, J.; Kawai, H.; Williams, J. F. Ind. Eng. Chem. Res. 2003, 42, 5715-5720.
18. (c) Worley, S. D.; Sun, G. Trends Polym. Sci. 1996, 4, 364-370.
19. (a) Liang, J.; Owens, J. R.; Huang, T. S.; Worley, S. D. J. Appl. Polym. Sci. 2006, 101, 3448-3454.
20. (b) Liang, J.; Wu, R.; Huang, T. S.; Worley, S. D. J. Appl. Polym. Sci. 2005, 97, 1161-1166.
21. (a) Akdag, A.; Okur, S.; McKee, M. L.; Worley, S. D. J. Chem. Theory Comput. 2006, 2, 879-884.
22. (b) Akdag, A.; McKee, M. L.; Worley, S. D. J. Phys. Chem. A 2006, 110, 7621-7627.
23. Qian, L.; Sun, G. J. Appl. Polym. Sci. 2003, 89, 2418-2425, and references cited therein.
24. (a) Corral, R. A.; Orazi, O. O. J. Org. Chem. 1963, 28, 1100-1104.
25. (b) Petterson, R. C.; Grzeskowiak, U. J. Org. Chem. 1958, 24, 1414-1419.
26. Frisch, M. J. et al. Gaussian03, Revision C.02; Gaussian, Inc.: Wallingford, CT, 2004 (for the full citation see the Supporting Information).
27. Takano, Y.; Houk, K. N. J. Chem. Theory Comput. 2005, 1, 70-77.
28. (a) Cossi, M.; Rega, N.; Scalmani, G.; Barone, V. J. Comput. Chem. 2003, 24, 669-681.
29. (b) Klamt, A.; Schuurmann, G. J. Chem. Soc., Perkin Trans. 1993, 2, 799-805.
30. (c) Barone, V.; Cossi, M. J. Phys. Chem. A 1998, 102, 1995-2001.
31. (d) Cossi, M.; Barone, V.; Cammi, R.; Tomasi, J. Chem. Phys. Lett. 1996, 255, 327-335.
32. McKee, M. L. J. Phys. Chem. A 2003, 107, 6819-6827.
33. Camaioni, D. M.; Schwerdtfeger, C. A. J. Phys. Chem. A 2005, 109, 10795-10797.
34. For recent applications, see: (a) Acevedo, O.; Jorgensen, W. L. Org. Lett. 2004, 6, 2881-2884.
35. (b) Acevedo, O.; Jorgensen, W. L. J. Am. Chem. Soc. 2005, 127, 8829-8834.
36. (c) Acevedo, O.; Jorgensen, W. L. J. Org. Chem. 2006, 71, 4896-4902.
37. (d) Acevedo, O.; Jorgensen, W. L. J. Am. Chem. Soc. 2006, 128, 6141-6144.
38. (a) Jorgensen, W. L. BOSS, version 4.6; Yale University: New Haven, CT, 2004.
39. (b) Jorgensen, W. L.; Tirado-Rives, J. J. Comput. Chem. 2005, 26, 1689-1700.
40. Jorgensen, W. L.; Chandrasekhar, J.; Madura, J. D.; Impey, W.; Klein, M. L. J. Chem. Phys. 1983, 79, 926-935.
41. Jorgensen, W. L. In Encyclopedia of Computational Chemistry; Schleyer, P. v. R., Ed.; Wiley: New York, 1998; Vol. 3, pp 1754-1763.
42. Repasky, M. P.; Chandrasekhar, J.; Jorgensen, W. L. J. Comput. Chem. 2002, 23, 1601-1622.
43. Thompson, J. D.; Cramer, C. J.; Truhlar, D. G. J. Comput. Chem. 2003, 24, 1291-1304.
44. Udier-Blagović, M.; Morales De Tirado, P.; Pearlman, S. A.; Jorgensen, W. L. J. Comput. Chem. 2004, 25, 1322-1332.
45. (a) Tubert-Brohman, I.; Guimarães, C. R. W.; Repasky, M. P.; Jorgensen, W. L. J. Comput. Chem. 2004, 25, 138-150.
46. (b) Vayner, G.; Houk, K. N.; Jorgensen, W. L.; Brauman, J. I. J. Am. Chem. Soc. 2004, 126, 9054-9058.
47. For prior studies of hydantoin tautomers, see: (a) Kleinpeter, E. Struct. Chem. 1997, 8, 161-173.
48. (b) Bausch, M. J.; David, B.; Dobrowolski, P.; Guadalupe-Fasano, C.; Gostowski, R.; Selmarten, D.; Prasad, V.; Vaughn, A.; Wang, L. H. J. Org. Chem. 1991, 56, 5643-5651.
49. (c) Bagno, A.; Comuzzi, C. Eur. J. Org. Chem. 1999, 287-295.
50. (d) Kleinpeter, E.; Heydenreich, M.; Kalder, L.; Koch, A.; Henning, D.; Kempter, G.; Benassi, R.; Taddei, F. J. Mol. Struct. 1997, 403, 111-122.
51. a value of 9.03 gives ΔG = 12.3 kcal/mol. However, the free energy is increased by 2.4 kcal/mol to account for the concentration of liquid water. See: Da Silva, C. O.; Da Silva, E. C.; Nascimento, M. A. C. J. Phys. Chem. A 1999, 103, 11194-11199.
52. Baboul, A. G.; Schlegel, H. B. J. Chem. Phys. 1997, 107, 9413-9417.