Permanganate oxidation of alkenes. Substituent and solvent effects. Difficulties with MP2 calculations

Journal of the American Chemical Society

Volumn 128, Issue 35, 2006, Pages 11537-11544

  Wiberg, Kenneth B ^a   Wang, Yi Gui ^a   Sklenak, Stepan ^a,c   Deutsch, Carol ^a,d   Trucks, Gary ^b  

^a YALE UNIVERSITY   (United States)

^b GAUSSIAN INC   (United States)

^c J HEYROVSKÝ INSTITUTE OF PHYSICAL CHEMISTRY   (Czech Republic)

^d UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ENERGY; CALORIMETRY; ETHANE; PERMITTIVITY; REACTION KINETICS; SUBSTITUTION REACTIONS;

CHARGE DIPOLE COMPLEX; PERMANGANATE OXIDATION; REACTANTS; TRANSITION STATE STRUCTURES;

OLEFINS;

ACRYLONITRILE; ALKENE DERIVATIVE; ALLYL ALCOHOL; CHROMIC ACID; CROTONIC ACID DERIVATIVE; PERMANGANATE POTASSIUM; SOLVENT;

ARTICLE; CALCULATION; CALORIMETRY; CHEMICAL REACTION KINETICS; DIELECTRIC CONSTANT; DIPOLE; ENERGY TRANSFER; MATHEMATICAL COMPUTING; OXIDATION KINETICS; SOLVENT EFFECT; SUBSTITUTION REACTION; SURFACE CHARGE;

EID: 33748359905     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0630184     Document Type: Article

References (35)

1. Allred, A. L.; Rochow, E. G. J. Inorg. Nucl. Chem. 1958, 2, 264.
2. Wiberg, K. B.; Geer, R. D. J. Am. Chem. Soc. 1966, 88, 5827.
3. Lee, D. G.; Brownridge, J. R. J. Am. Chem. Soc. 1974, 96, 5517.
4. Boeseken, J. Recl. Trav. Chim. Pays-Bas 1921, 40 553;
5. Boeseken, J. Recl. Trav. Chim. Pays-Bas 1928, 47, 1083.
6. Wiberg, K. B.; Saegebarth, K. A. J. Am. Chem. Soc. 1957, 79, 2822.
7. Wagner, G. J. Russ. Phys. Chem. Soc. 1895, 27, 219.
8. Freeman, F.; Kappos, J. C. J. Org. Chem. 1986, 51, 1654.
9. Larger substituent effects were found when the oxidation was carried out in acetic anhydride (Nelson, B.; Henley, R. L. Tetrahedron Lett. 1995, 36, 6375).
10. Lapworth, A.; Mottram, E. N. J. Chem. Soc. 1925, 127, 1628.
11. King, G. J. Chem. Soc. 1931, 1874.
12. Coleman. J. E.; Ricciuti, C.; Swern, S. J. Am. Chem. Soc. 1956, 78, 5432.
13. Allen, M. B.; Ruberg, S. J. Am. Chem. Soc. 1942, 64, 948.
14. Simandi, L. I.; Jáky, M. J. Chem. Soc., Perkin. Trans. 2 1973, 1856.
15. Jáky, M.; Simándi, L. I.; Maros, L.; Molnár-Perl, I. J. Chem. Soc., Perkin. Trans. 2 1973, 1565.
16. Wiberg, K. B.; Deutsch, C.; Rocek, J. J. Am. Chem. Soc. 1973, 95, 3034.
17. Lee, D. G.; Brownridge, J. R. J. Am. Chem. Soc. 1973, 95, 3033.
18. Houk, K. N.; Strassner, T. J. Org. Chem. 1999, 64, 800.
19. Strassner, T.; Busold, M. J. Org. Chem. 2001, 66, 672.
20. Strassner, T.; Busold, M. J. Phys. Chem. A. 2004, 108, 4455.
21. Pellerite, M. J.; Brauinan, J. I. J. Am. Chem. Soc. 1983, 105, 2672.
22. Cappelli, S.; Corni, B.; Mennucci, B.; Cainini, R.; Tomasi, J. J. Phys. Chem. A 2002, 106, 12331,
23. Cossi, M.; Scalmani, G.; Rega, N.; Barone, V. J. Chem. Phys. 2002, 117, 43.
24. Cf. Wiberg, K. B. J. Org. Chem. 2003, 65, 9322.
25. Carlier, P. R.; Deora, N.; Crawford, T. D. J. Org. Chem. 2006, 71, 1592.
26. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople. J. A. Ab Initio Molecular Orbital Theory; Wiley: New York, 1986; p 90ff.
27. Cao, Z.; Wu, W.; Zhang, Q. THEOCHEM 1999, 489, 165.
28. Bartlett, R. J. In Modern Electronic Structure Theory; Yarkony, D. R. Ed.; Advanced Series in Physical Chemistry, Vol. 2; World Scientific: Singapore, 1995.
29. Crawford, T. D.; Schaefer, H. F. In Reviews in Computational Chemistry, Lipkowite, K. B., Boyd, D. B., Eds.; VCH Publishers: New-York, 2000.
30. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899.
31. It would have been desirable to carry out CCSD calculations for the reaction of allyl alcohol. However, it has an addition rotational degree of freedom, and the DFT calculations indicate that the location of the proton is important. As a result, it was beyond our present computational capabilities.
32. For a preliminary report on this study, see ref 10.
33. Deutsch, C. J. In Computer Programs for Chemistry, DeTar, D. F, Ed.; Benjamin: New York, 1972; Vol. IV.
34. Eggers, D. F., Jr.; Gregory, N. W.; Halsey, G. D., Jr; Rabinovitch, B. S. Physical Chemistry; Wiley: New York, 1964; p 291.
35. Frisch, M. J. et al. Gaussian-03, revision B.07; Gaussian, Inc.: Wallingford, CT, 2004.