Solvent effects on the activation barriers of olefin epoxidation - A density functional study

European Journal of Organic Chemistry

Volumn , Issue 4, 2001, Pages 719-723

  Gisdakis, Philip ^a   Rösch, Notker ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

Density functional calculations; Epoxidations; Peroxides; Peroxo complexes; Solvent effects

Indexed keywords

ALKANE; CARBOXYLIC ACID DERIVATIVE; ETHYLENE OXIDE DERIVATIVE; PEROXIDE; RHENIUM COMPLEX; SOLVENT;

ARTICLE; CHEMICAL REACTION; COMPLEX FORMATION; DIELECTRIC CONSTANT; ENERGY; EPOXIDATION; POLARIZATION;

EID: 0035134653     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200102)2001:4<719::AID-EJOC719>3.0.CO;2-6     Document Type: Article

References (33)

1. W. Adam, R. Curci, J. O. Edwards, Acc. Chem. Res. 1989, 22, 205.
2. R. W. Murray, Chem. Rev. 1989, 89, 1187.
3. B. M. Lynch, K. H. Pausacker, J. Chem. Soc. 1955, 1525.
4. Y. Ogata, Y. Sawaki, H. Inoue, J. Org. Chem. 1973, 38, 1044.
5. Y. S. Angelis, M. Orfanopoulos, J. Org. Chem. 1997, 62, 6083.
6. W. Adam, D. Golsch, Chem. Ber. 1994, 127, 1111.
7. W. Adam, D. Golsch, J. Org. Chem. 1997, 62, 115.
8. D. A. Singleton, S. R. Merrigan, J. Liu, K. N. Houk, J. Am. Chem. Soc. 1997, 119, 3385.
9. R. D. Bach, C. M. Estévez, J. E. Winter, M. N. Glukhovtsev, J. Am. Chem. Soc. 1998, 120, 680.
10. X. Du, K. N. Houk, J. Org. Chem. 1998, 63, 6480.
11. M. Freccero, R. Gandolfi, M. Sarzi-Amadè, A. Rastelli, Tetrahedron 1998, 54, 6123.
12. M. N. Glukhovtsev, C. Canepa, R. D. Bach, J. Am. Chem. Soc. 1998, 120, 10528.
13. J. Liu, K . N. Houk, A. Dinoi, C. Fusco, R. Curci, J. Org. Chem. 1998, 63, 8565.
14. R. D. Bach, M. N. Glukhovtsev, C. Gonzalez, M. Marquez, C. M. Estevéz, A. G. Baboul, H. B. Schlegel, J. Phys. Chem. A 1997, 101, 6092.
15. P. Gisdakis, N. Rösch, J. Org. Chem. 2001, in print.
16. I. V. Yudanov, C. Di Valentin, P. Gisdakis, N. Rösch, Eur. J. Inorg. Chem. 1999, 2135.
17. C. Di Valentin, P. Gisdakis, I. V. Yudanov, N. Rösch, J. Org. Chem. 2000, 65, 2996.
18. N. Rösch, P. Gisdakis, I. V. Yudanov, C. Di Valentin, in Peroxide Chemistry: Mechanistic and Preparative Aspects of Oxygen Transfer (Ed.: W. Adam), Wiley-VCH, Weinheim, 2000, p. 601.
19. F. E. Kühn, A. M. Santos, P. W. Roesky, E. Herdtweck, W. Scherer, P. Gisdakis, I. V. Yudanov, C. Di Valentin, N. Rösch, Chem. Eur. J. 1999, 5, 3603.
20. A. Görling, S. B. Trickey, P. Gisdakis, N. Rösch, in Topics in Organometallic Chemistry, Vol. 4 (Eds.: J. M. Brown, P. Hofmann), Springer, Heidelberg, 1999, 109.
21. R. W. Murray, D. Gu, J. Chem. Soc., Perkin Trans. 1993, 2, 2203.
22. J. Tomasi, M. Persico, Chem. Rev. 1994, 94, 2027.
23. C. J. Cramer, D. G. Truhlar, Chem. Rev. 1999, 99, 2161.
24. A. D. Becke, J. Chem. Phys. 1993, 98, 5648.
25. C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785.
26. Gaussian 98, Revision A.7, J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery Jr., R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, 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. Johnson, W. Chen, M. W. Wong, J. L. Andres, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian Inc.: Pittsburgh PA, 1998.
27. R. Krishnan, J. Binkley, R. Seeger, J. A. Pople, J. Chem. Phys. 1980, 72, 650.
28. A. McLean, G. Chandler, J. Chem. Phys. 1980, 72, 5639.
29. C. Amovilli, V. Barone, R. Cammi, E. Cances, M. Cossi, B. Mennucci, C. S. Pomelli, J. Tomasi, Adv. Quantum. Chem. 1999, 32, 227.
30. J. March, Advanced Organic Chemistry, 3rd ed. Wiley, New York, 1985, 220.
31. CRC Handbook of Chemistry and Physics, 77th Ed. CRC: New York, 1997.
32. P. Gisdakis, S. Antonczak, S. Köstlmeier, W. A. Herrmann, N. Rösch, Angew. Chem. Int. Ed. 1998, 37, 2211.
33. J. J. Haider Dissertation, Technische Universität München, 1999.