Computational study of the general base catalysed aminolysis of 2-benzoxazolinone

Journal of Molecular Structure: THEOCHEM

Volumn 633, Issue 1, 2003, Pages 49-55

  Ilieva, Sonia ^a   Atanasov, Yasen ^a   Kalcheva, Veneta ^a   Galabov, Boris ^a  

^a UNIVERSITY OF SOFIA   (Bulgaria)

Author keywords

2(3H) Benzoxazolone; 2 Benzoxazolinone; Aminolysis; Computations; Mechanism of aminolysis

Indexed keywords

2 BENZOXAZOLONE DERIVATIVE; AMINE; METHYLAMINE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; GAS; RING OPENING; THEORETICAL STUDY;

EID: 0043065391     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0166-1280(03)00310-5     Document Type: Article

References (34)

1. J.F. Bunnett, G.T. Davis, J. Am. Chem. Soc. 82 (1991) 665.
2. W.P. Jencks, J. Carriuolo, J. Am. Chem. Soc. 82 (1960) 675.
3. T.C. Bruice, M.F. Mayahi, J. Am. Chem. Soc. 82 (1960) 3067.
4. G.M. Blackburn, W.P. Jencks, J. Am. Chem. Soc. 90 (1968) 2638.
5. W.P. Jencks, M. Gilchrist, J. Am. Chem. Soc. 88 (1966) 104.
6. T.C. Bruice, A. Donzel, R.W. Huffman, A.R. Butler, J. Am. Chem. Soc. 89 (1967) 2106.
7. G.A. Rogers, T.C. Bruice, J. Am. Chem. Soc. 95 (1973) 4452.
8. G.A. Rogers, T.C. Bruice, J. Am. Chem. Soc. 96 (1974) 2473.
9. A. Williams, Acc. Chem. Res. 22 (1989) 387.
10. M. Page, A. Williams, Organic and Bioorganic Mechanisms, Longman, Harlow, 1997.
11. R.A.J. O'Hair, N.K. Androutsopoulos, Org. Lett. 2 (2000) 2567.
12. C.K. Kim, H.G. Li, H.W. Lee, C.K. Sohn, Y.I. Chun, I. Lee, J. Phys. Chem. 104 (2000) 4069.
13. N. Diaz, D. Suarez, T. Sordo, Chem. Eur. J. 5 (1999) 1045.
14. N. Diaz, D. Suarez, T. Sordo, J. Org. Chem. 64 (1999) 3281.
15. N. Diaz, D. Suarez, T. Sordo, J. Org. Chem. 64 (1999) 9144.
16. N. Diaz, D. Suarez, T. Sordo, J. Am. Chem. Soc. 122 (2000) 6710.
17. N. Diaz, D. Suarez, T. Sordo, Eur. J. Org. Chem. (1999) 793.
18. W. Yang, D.G. Drueckhammer, Org. Lett. 2 (2000) 4133.
19. H. Zipse, L. Wang, K.N. Houk, Liebigs Ann. (1996) 1511.
20. L. Wang, H. Zipse, Liebigs Ann. (1996) 1501.
21. H. Adalstensson, T.C. Bruice, J. Am. Chem. Soc. 120 (1998) 3440.
22. S. Ilieva, B. Galabov, D.G. Musaev, K. Morokuma, H.F. Schaefer, J. Org. Chem. 68 (2003) 1496.
23. H. Ucar, K. Van derpoorten, S. Cacciaguerra, S. Spampinato, J.P. Stables, P. Depovere, M. Isa, B. Masereel, J. Delarge, J.H. Poupaert, J. Med. Chem. 41 (1998) 1138.
24. J. Sam, J. Valentine, J. Pharm. Sci. 58 (1969) 1043.
25. T. Sheradsky, S. Arvamovici-Grisary, Tetrahedron Lett. 26 (1978) 2325.
26. N.N. Melnikov, Pesticides, Khimia, Moscow, 1987.
27. V.R. Twele, G. Spiteller, Drug Res. 32 (1982) 759.
28. S. Ilieva, B. Galabov, D.G. Musaev, K. Morokuma, J. Org. Chem. 68 (2003) 3406.
29. A.D. Becke, Phys. Rev. 38 (1988) 3098.
30. C. Lee, W. Yang, R.G. Parr, Phys. Rev. B 37 (1988) 785.
31. S.H. Vosko, L. Wilk, M. Nusair, Can. J. Phys. 58 (1980) 1200.
32. C. Gonzalez, H.B. Schlegel, J. Chem. Phys. 90 (1989) 2154.
33. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.A. Montgomery, R.E. Stratmann, J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P.M.W. Gill, B.G. Johnson, W. Chen, M.W. Wong, J.L. Andres, M. Head-Gordon, E.S. Replogle, J. A. Pople, GAUSSIAN 98 (Revision A.7), Gaussian, Inc. Pittsburgh PA, 1998.
34. D. Simov, V. Kalceva, M. Arnaudov, B. Galabov, CR Acad. Bulg. Sci. 21 (1968) 877.