C-H activation in reactions of protonated hydrogen peroxide with propane. Remarkable regioselectivity for hydride abstraction and mechanism for acid catalyzed hydrogen exchange

International Journal of Mass Spectrometry

Volumn 254, Issue 3, 2006, Pages 189-196

  Adlhart, Christian ^a   Uggerud, Einar ^a  

^a UNIVERSITY OF OSLO   (Norway)

Author keywords

Alkanium ions; Carbocations; Hydride abstraction; Mass spectrometry; Proton transfer; Quantum chemistry; Reaction mechanism

Indexed keywords

EID: 33746314005     PISSN: 13873806     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ijms.2006.05.018     Document Type: Article

References (36)

1. Arakawa H., Aresta M., Armor J., Barteau M., Beckman E., Bell A., Bercaw J., Creutz C., Dixon D.A., Dixon D., Domen K., DuBois D., Eckert J., Fujita E., Gibson D., Goddard W., Goodman D., Keller J., Kubas G., Kung H., Lyons J., Manzer L., Marks T., Morokuma K., Nicholas K., Periana R., Que L., Rostrup-Nielson J., Sachtler W., Schmidt L., Sen A., Somorjai G., Stair P., Stults B., and Tumas W. Chem. Rev. 101 (2001) 953
2. Labinger J.A. J. Mol. Catal. A: Chem. 220 (2004) 27
3. Lersch M., and Tilset M. Chem. Rev. (Washington, DC, United States) 105 (2005) 2471
4. Oiestad A.M.L., Petersen A.C., Bakken V., Vedde J., and Uggerud E. Angew. Chem. Int. Ed. 40 (2001) 1305
5. Olah G.A., Keumi T., Lecoq J.C., Fung A.P., and Olah J.A. J. Org. Chem. 56 (1991) 6148
6. Olah G.A., Parker D.G., and Yoneda N. Angew. Chem. 90 (1978) 962
7. Olah G.A., Yoneda N., and Parker D.G. J. Am. Chem. Soc. 99 (1977) 483
8. Bach R.D., and Su M.-D. J. Am. Chem. Soc. 116 (1994) 10103
9. Adlhart C., Sekiguchi O., and Uggerud E. Chem. Eur. J. 11 (2005) 152
10. Olah G.A., Klopman G., and Schlosberg R.H. J. Am. Chem. Soc. 91 (1969) 3261
11. Olah G.A., and Schlosberg R.H. J. Am. Chem. Soc. 90 (1968) 2726
12. Hogeveen H., and Bickel A.F. Recl. Trav. Chim. Pays-Bas 88 (1969) 371
13. Tal'rose V.L., and Lyubimova A.K. Dokl. Akad. Nauk. SSSR 86 (1952) 909
14. Futrell J.H. J. Phys. Chem. 65 (1961) 565
15. White E.T., Tang J., and Oka T. Science 284 (1999) 135
16. Goeppert A., Sassi A., Sommer J., Esteves P.M., Mota C.J.A., Karlsson A., and Ahlberg P. J. Am. Chem. Soc. 121 (1999) 10628
17. Konishi T., Yoshida K., and Hayashi K. In: Koho J.K.T. (Ed). Processes for Manufacturing Peroxidized Urea (2003)
18. Adams N.G., Smith D., and Paulson J.F. J. Chem. Phys. 72 (1980) 4951
19. Ikezoe Y., Matsuoka S., Takebe M., and Viggiano A. Gas Phase Ion-Molecule Reaction Rate Constants through 1986 (1987), Maruzen, Tokyo
20. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery J.A., Vreven T., Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J.E., Hratchian H.P., Cross J.B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Ayala P.Y., Morokuma K., Voth G.A., Salvador P., Dannenberg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas O., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Gonzalez C., and Pople J.A. Gaussian 03, Revision C.02 (2004), Gaussian, Inc., Wallingford, CT
21. Curtiss L.A., Raghavachari K., Redfern P.C., Rassolov V., and Pople J.A. J. Chem. Phys. 109 (1998) 7764
22. Laerdahl J.K., and Uggerud E. Org. Biomol. Chem. 1 (2003) 2935
23. Oiestad E.L., Harvey J.N., and Uggerud E. J. Phys. Chem. A 104 (2000) 8382
24. Oiestad E.L., and Uggerud E. Int. J. Mass Spectrom. 185/186/187 (1999) 231
25. Beauchamp J.L. In: Armentrout P.B. (Ed). Encyclopedia of Mass Spectrometry, volume 1: Theory and Ion Chemistry (2003), Elsevier, Amsterdam 843
26. Adlhart C., and Uggerud E. Phys. Chem. Chem. Phys. 9 (2006) 1066
27. Lias S.G., Bartmess J.E., Liebman J.F., Holmes J.L., Levin R.D., and Mallard W.G. J. Phys. Chem. Ref. Data, Suppl. 17 (1988) 1
28. Uggerud E. Eur. J. Mass Spectrom. 6 (2000) 131
29. Esteves P.M., Mota C.J.A., Ramirez-Solis A., and Hernandez-Lamoneda R. J. Am. Chem. Soc. 120 (1998) 3213
30. Hirschfelder J.O. J. Chem. Phys. 6 (1938) 795
31. Dykstra C.E., Gaylord A.S., Gwinn W.D., Swope W.C., and Schaefer H.F. J. Chem. Phys. 68 (1978) 3951
32. Oka T. Phys. Rev. Lett. 45 (1980) 531
33. Yeh L.I., Price J.M., and Lee Y.T. J. Am. Chem. Soc. 111 (1989) 5597
34. Esteves P.M., Ramirez-Solis A., and Mota C.J.A. J. Braz. Chem. Soc. 11 (2000) 345
35. Arzumanov S.S., Reshetnikov S.I., Stepanov A.G., Parmon V.N., and Freude D. J. Phys. Chem. B 109 (2005) 19748
36. NIST, Standard Reference Database Number 69, 2005, http://webbook.nist.gov/chemistry/.