The faster conversion of ethene thiol than vinyl alcohol in tautomerization reactions in aqueous solution - Theoretical prediction

Journal of Molecular Structure: THEOCHEM

Volumn 461-462, Issue , 1999, Pages 581-588

  Suenobu, Katsuhiro ^a,d   Nagaoka, Masataka ^a,c   Yamabe, Tokio ^b  

^a INSTITUTE FOR FUNDAMENTAL CHEMISTRY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

^c NAGOYA UNIVERSITY   (Japan)

^d SUMITOMO CHEMICAL CO LTD   (Japan)

Author keywords

Ab initio molecular orbital (MO) method; Charge separated ion pair (CSIP); Ethene thiol thioacetaldehyde tautomerization; Isodensity polarizable continuum model (IPCM) method; Vinyl alcohol acetaldehyde tautomerization

Indexed keywords

ALCOHOL DERIVATIVE; ETHYLENE; THIOL DERIVATIVE; VINYL DERIVATIVE;

AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CHEMICAL REACTION; DIPOLE; MOLECULAR MODEL; PROTON TRANSPORT;

EID: 0033515402     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0166-1280(98)00474-6     Document Type: Article

References (15)

1. Z. Rappoport (Ed.), The Chemistry of Enols, Wiley, New York, 1990.
2. Capon B., Guo B., Kwok F.C., Siddhanta A.K., Zucco C. Acc. Chem. Res. 21:1988;135.
3. Smith B.J., Nguyen M.T., Bouma W.J., Radom L. J. Am. Chem. Soc. 113:1991;6452.
4. Ventura O.N., Lledos A., Bonaccorsi R., Bertran J., Tomasi J. Theor. Chim. Acta. 72:1987;175.
5. Poirier R.A., Yu D., Surjan P.R. Can. J. Chem. 69:1991;1589.
6. Nagaoka M., Suenobu K., Yamabe T. J. Am. Chem. Soc. 119:1997;8023.
7. Capon B., Zucco C. J. Am. Chem. Soc. 104:1982;7567.
8. Chiang Y., Hojatti M., Keefe J.R., Kresge A.J., Schepp N.P., Wirz J. J. Am. Chem. Soc. 109:1987;4000.
9. Curtiss L.A., Raghavachari K., Trucks G.W., Pople J.A. J. Chem. Phys. 94:1991;7221.
10. Pople J.A., Head-Gordon M., Fox D.J., Raghavachari K., Curtiss L.A. J. Chem. Phys. 90:1989;5622.
11. Williams G.A., Macdonald J.N., Dunn K.M., Boggs J.E. Spectrochim. Acta. 48A:1992;783.
12. Ahmad M.R., Dahlke G.D., Kass S.R. J. Am. Chem. Soc. 118:1996;1398.
13. Lammertsma K., Prasad B.V. J. Am. Chem. Soc. 116:1994;642.
14. 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. 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 and J.A. Pople, Gaussian94, Revision C.3, Gaussian, Inc., Pittsburgh, PA, 1995.
15. Foresman J.B., Keith T.A., Wiberg K.B., Snoonian J., Frisch M.J. J. Phys. Chem. 100:1996;16098.