Theoretical study on oxygen exchange accompanying alkaline hydrolysis of esters and amides. The role of water for the exchange reaction

Journal of Molecular Structure: THEOCHEM

Volumn 461-462, Issue , 1999, Pages 589-596

  Hori, Kenzi ^a   Hashitani, Yuji ^b   Kaku, Yuji ^b   Ohkubo, Katsutoshi ^b  

^a YAMAGUCHI UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

Ab initio molecular orbital calculations; Direct mechanism; Monte Carlo simulations; Oxygen exchange; Water assisted mechanism

Indexed keywords

AMIDE; ESTER DERIVATIVE; OXYGEN; WATER;

ARTICLE; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; HYDROLYSIS; MOLECULAR MODEL; PROTON TRANSPORT; REACTION ANALYSIS;

EID: 17544391536     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0166-1280(98)00473-4     Document Type: Article

References (26)

1. Bender M.L., Heck H.D. J. Am. Chem. Soc. 89:1967;1211.
2. Bender M.L. J. Am. Chem. Soc. 73:1951;1626.
3. R.A.Y. Jones, Physical and Mechanistic Organic Chemistry, Cambridge University Press, Cambridge, 1979, pp. 227-246.
4. Hori K., Kamimura A., Ando K., Nakao Y., Mizumura M., Ihara Y. Tetrahedron. 53:1997;4317.
5. K. Hori, A. Kamimura, Y. Nakao, Y. Ihara, Atualidades de Fisico-Quimica Organica (1995) 271.
6. Hori K., Kamimura A., Kimoto J., Gotoh S., Ihara Y. J. Chem. Soc. Perkin Trans. 2:1994;2053.
7. Hori K. J. Chem. Soc. Perkin Trans. 2:1992;1629.
8. Alagona G., Scrocco E., Tomasi J. J. Am. Chem. Soc. 97:1975;6976.
9. Oie T., Loew G.H., Burt S.K., Binkley J.S., MacElroy R.D. J. Am. Chem. Soc. 104:1982;6169.
10. Jensen J.H., Baldridge K.K., Gordon M.S. J. Phys. Chem. 96:1992;8340.
11. Antonczak S., Ruiz-López M.F., Rivail J.L. J. Am. Chem. Soc. 116:1994;3912.
12. Bender M.L. Chem. Rev. 60:1960;53.
13. Bunton C.A., Nayak B., O'Connor C. J. Org. Chem. 33:1968;572.
14. Brown R.S., Bennet A.J., Slebocka-Tilk H. Acc. Chem. Res. 25:1992;481.
15. Guthrie J.P. J. Am. Chem. Soc. 95:1973;6999.
16. Guthrie J.P. J. Am. Chem. Soc. 96:1974;3608.
17. Yamazaki-Nishida S., Cervera-March S., Nagano K.J., Anderson M.A., Hori K. J. Phys. Chem. 99:1995;1514.
18. Nagaoka M., Okuno Y., Yamabe T. J. Am. Chem. Soc. 113:1991;769.
19. M.J. Frisch, G.W. Trucks, H.B. Schlegel, P.M.W. Gill, B.G. Johnson, M.A. Robb, J.R. Cheeseman, T. Keith, G.A. Petersson, J.A. Montgomery, K. Raghavachari, M.A. Al-Laham, V.G. Zakrzewski, J.V. Ortiz, J.B. Foresman, J. Cioslowski, B.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, Gaussian94, Gaussian, Inc., Pittsburgh, PA, 1995.
20. Breneman C.M., Weiberg K.B. J. Comp. Chem. 11:1990;361.
21. Madura J.D., Jorgensen W.L. J. Am. Chem. Soc. 108:1986;2517.
22. Jorgensen W.L., Gao J. J. Am. Chem. Soc. 110:1988;4212.
23. W.L. Jorgensen, Boss, Version 3.5, Yale University, New Haven, CT, 1994.
24. W.J. Hehre, L. Radom, P.v.R. Schleyer, J.A. Pople, Ab Initio Molecular Orbital Theory, John Wiley, 1986, p. 258.
25. Kollman P.A., Merts K.M. Acc. Chem. Res. 23:1990;246.
26. Jorgensen W.L. Acc. Chem. Soc. 22:1989;184.