The Carbocation Rearrangement Mechanism, Clarified

Journal of Organic Chemistry

Volumn 81, Issue 4, 2016, Pages 1410-1415

  Sandbeck, Daniel J S ^a   Markewich, Daniel J ^a   East, Allan L L ^a  

^a UNIVERSITY OF REGINA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

MOLECULAR DYNAMICS; QUANTUM CHEMISTRY; REACTION KINETICS;

CHEMICAL EQUATIONS; ELEMENTARY STEPS; ION REARRANGEMENT; ISOTOPE LABELING EXPERIMENTS; ORGANIC REACTION; PRODUCT DISTRIBUTIONS; QUANTUM CHEMICAL COMPUTATIONS; REARRANGEMENT MECHANISMS;

PROTONATION;

PETROLEUM;

ARTICLE; CARBOCATION REARRANGEMENT; CHEMICAL REACTION; DENSITY FUNCTIONAL THEORY; ENERGY; ENTHALPY; JOINT MOBILITY; MOLECULAR DYNAMICS; QUANTUM CHEMISTRY; SURFACE PROPERTY;

EID: 84959019715     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/acs.joc.5b02553     Document Type: Article

References (43)

1. Naredla, R. R.; Klumpp, D. A. Chem. Rev. 2013, 113, 6905 10.1021/cr4001385
2. Smith, M. B. March's Advanced Organic Chemistry, 7 th ed.; Wiley: Hoboken, NJ, 2013; pp 1526-7.
3. Olah, G. A.; Surya Prakash, G. K.; Molnár, A.; Sommer, J. Superacid Chemistry, 2 nd ed.; Wiley: Hoboken, NJ, 2009; p 527.
4. Brouwer, D. M. Recl. Trav. Chim. Pays Bas 1968, 87, 210 10.1002/recl.19680870212
5. Brouwer, D. M.; Oelderik, J. M. Recl. Trav. Chim. Pays Bas 1968, 87, 721 10.1002/recl.19680870614
6. Brouwer, D. M.; Hogeveen, H. Prog. Phys. Org. Chem. 1972, 9, 179 10.1002/9780470171882.ch4
7. Klein, M. T.; Hou, G.; Bertolacini, R. J.; Broadbelt, L. J.; Kumar, A. Molecular Modeling in Heavy Hydrocarbon Conversions, 1 st ed.; CRC Press: Boca Raton, FL, 2006.
8. Bennett, C. A.; Klein, M. T. Energy Fuels 2012, 26, 41 10.1021/ef201136z
9. Collins, C. J. Chem. Rev. 1969, 69, 543 10.1021/cr60260a004
10. Radom, L.; Pople, J. A.; Buss, V.; Schleyer, P. v. R. J. Am. Chem. Soc. 1971, 93, 1813 10.1021/ja00736a059
11. J. Am. Chem. Soc. 1972, 94, 311. 10.1021/ja00757a001
12. Nevell, T. P.; de Salas, E.; Wilson, C. L. J. Chem. Soc. 1939, 1188 10.1039/jr9390001188
13. East, A. L. L.; Bučko, T.; Hafner, J. J. Phys. Chem. A 2007, 111, 5945 10.1021/jp072327t
14. East, A. L. L.; Bučko, T.; Hafner, J. J. Chem. Phys. 2009, 131, 104314 10.1063/1.3230603
15. Olah, G. A. J. Org. Chem. 2001, 66, 5943 10.1021/jo010438x
16. Olah, G. A.; White, A. M. J. Am. Chem. Soc. 1969, 91, 3954 10.1021/ja01042a053
17. Olah, G. A.; White, A. M. J. Am. Chem. Soc. 1969, 91, 3956 10.1021/ja01042a054
18. Yannoni, C. S.; Macho, V.; Myhre, P. C. J. Am. Chem. Soc. 1982, 104, 7380 10.1021/ja00389a108
19. Scholz, F.; Himmel, D.; Heinemann, F. W.; Schleyer, P. v. R.; Meyer, K.; Krossing, I. Science 2013, 341, 62 10.1126/science.1238849
20. Saunders, M.; Vogel, P.; Hagen, E. L.; Rosenfeld, J. Acc. Chem. Res. 1973, 6, 53 10.1021/ar50062a003
21. Carneiro, J. W. de M.; Schleyer, P. v. R.; Koch, W.; Raghavachari, K. J. Am. Chem. Soc. 1990, 112, 4064 10.1021/ja00166a068
22. Sieber, S.; Buzek, P.; Schleyer, P. v. R.; Koch, W.; Carneiro, J. W. de M. J. Am. Chem. Soc. 1993, 115, 259 10.1021/ja00054a037
23. Wagaye, A. M. M.Sc. Thesis, University of Regina, Regina, SK, 2011.
24. Kresse, G.; Hafner, J. Phys. Rev. B: Condens. Matter Mater. Phys. 1993, 47, 558 10.1103/PhysRevB.47.558
25. Kresse, G.; Furthmüller, J. Phys. Rev. B: Condens. Matter Mater. Phys. 1996, 54, 11169 10.1103/PhysRevB.54.11169
26. Kresse, G.; Hafner, J. J. Phys.: Condens. Matter 1994, 6, 8245 10.1088/0953-8984/6/40/015
27. Kresse, G.; Joubert, D. Phys. Rev. B: Condens. Matter Mater. Phys. 1999, 59, 1758 10.1103/PhysRevB.59.1758
28. Nosé, S. A. J. Chem. Phys. 1984, 81, 511 10.1063/1.447334
29. Leach, A. R. Molecular Modelling: Principles and Applications, 2 nd ed.; Pearson Education Ltd.: Harlow, U.K., 2001.
30. Humphrey, W.; Dalke, A.; Schulten, K. J. Mol. Graphics 1996, 14, 33 10.1016/0263-7855(96)00018-5
31. Perdew, J. P.; Zunger, A. Phys. Rev. B: Condens. Matter Mater. Phys. 1981, 23, 5048 10.1103/PhysRevB.23.5048
32. Vosko, S. H.; Wilk, L.; Nusair, M. Can. J. Phys. 1980, 58, 1200 10.1139/p80-159
33. Perdew, J. P.; Burke, K.; Ernzerhof, M. Phys. Rev. Lett. 1996, 77, 3865 10.1103/PhysRevLett.77.3865
34. Phys. Rev. Lett. 1997, 78, 1396. 10.1103/PhysRevLett.78.1396
35. Frisch, M. J.; Gaussian 09, revision B.01; Gaussian, Inc.: Wallingford, CT, 2010.
36. Scuseria, G. E.; Janssen, C. L.; Schaefer, H. F., III J. Chem. Phys. 1988, 89, 7382 10.1063/1.455269
37. Olah, G. A.; Lukas, J. J. Am. Chem. Soc. 1967, 89, 4739 10.1021/ja00994a030
38. Johnson, S. A.; Clark, D. T. J. Am. Chem. Soc. 1988, 110, 4112 10.1021/ja00221a002
39. Olah, G. A.; DeMember, J. R.; Commeyras, A.; Bribes, J. L. J. Am. Chem. Soc. 1971, 93, 459 10.1021/ja00731a025
40. Karabatsos, G. J.; Orzech, C. E., Jr.; Fry, J. L.; Meyerson, S. J. Am. Chem. Soc. 1970, 92, 606 10.1021/ja00706a031
41. Skell, P. S.; Starer, I.; Krapcho, A. P. J. Am. Chem. Soc. 1960, 82, 5257 10.1021/ja01504a070
42. Karabatsos, G. J.; Orzech, C. E., Jr.; Meyerson, S. J. Am. Chem. Soc. 1964, 86, 1994 10.1021/ja01064a017
43. Weitkamp, J.; Jacobs, P. A.; Martens, J. A. Appl. Catal. 1983, 8, 123 10.1016/0166-9834(83)80058-X