Reactions of 2-bromopropene radical cation with amines - A study by FT-ICR spectrometry and DFT calculation

International Journal of Mass Spectrometry

Volumn 228, Issue 2-3, 2003, Pages 167-180

  Büchner, Michael ^a   Grützmacher, Hans Friedrich ^a  

^a BIELEFELD UNIVERSITY   (Germany)

Author keywords

2 Bromopropene radical cation; DFT; Electron transfer; FT ICR; Ion molecule reaction; Nucleophilic substitution; Reaction mechanism

Indexed keywords

ALKENE DERIVATIVE; AMINE; AMMONIUM DERIVATIVE; BROMINE DERIVATIVE; RADICAL;

ARTICLE; CALCULATION; CHEMICAL BOND; CHEMICAL REACTION; ELECTRON TRANSPORT; ENERGY; FOURIER TRANSFORM ION CYCLOTRON RESONANCE SPECTROMETRY; IONIZATION; MASS SPECTROMETRY; MOLECULAR BIOLOGY; OXIDATION;

EID: 0041706188     PISSN: 13873806     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1387-3806(03)00206-9     Document Type: Article

References (36)

1. Marcus J.A. J. Chem. Phys. 24:1956;4966.
2. Marcus J.A. Angew. Chem. Int. Ed. Engl. 32:1993;1111.
3. Savéant J.-M. Acc. Chem. Res. 26:1993;455 (d) Murdoch J.R. J. Am. Chem. Soc. 94:1972;4410 (e) D.K. Böhme, in: P. Ausloos (Ed.), Interactions between Ions and Molecules, Plenum Press, New York, 1974, p. 489 (f) Formosinho S.J. J. Chem. Soc. Perkin Trans. 2:1987;61.
4. Savéant J.-M. Acc. Chem. Res. 26:1993;455 (d) Murdoch J.R. J. Am. Chem. Soc. 94:1972;4410 (e) D.K. Böhme, in: P. Ausloos (Ed.), Interactions between Ions and Molecules, Plenum Press, New York, 1974, p. 489 (f) Formosinho S.J. J. Chem. Soc. Perkin Trans. 2:1987;61.
5. Savéant J.-M. Acc. Chem. Res. 26:1993;455 (d) Murdoch J.R. J. Am. Chem. Soc. 94:1972;4410 (e) D.K. Böhme, in: P. Ausloos (Ed.), Interactions between Ions and Molecules, Plenum Press, New York, 1974, p. 489 (f) Formosinho S.J. J. Chem. Soc. Perkin Trans. 2:1987;61.
6. Savéant J.-M. Acc. Chem. Res. 26:1993;455 (d) Murdoch J.R. J. Am. Chem. Soc. 94:1972;4410 (e) D.K. Böhme, in: P. Ausloos (Ed.), Interactions between Ions and Molecules, Plenum Press, New York, 1974, p. 489 (f) Formosinho S.J. J. Chem. Soc. Perkin Trans. 2:1987;61.
7. For an overview see H.-F. Grützmacher, Curr. Org. Chem., in press.
8. Radom L. Org. Mass Spectrom. 26:1991;359.
9. (a) N. Heinrich, H. Schwarz, in: J.P. Maier (Ed.), Ion and Cluster Ion Spectroscopy and Structure, Elsevier, Amsterdam, 1989, p. 329 (b) Lammertsma K., von Rague Schleyer P., Schwarz H. Angew. Chem. Int. Ed. Engl. 28:1989;1321.
10. (a) N. Heinrich, H. Schwarz, in: J.P. Maier (Ed.), Ion and Cluster Ion Spectroscopy and Structure, Elsevier, Amsterdam, 1989, p. 329 (b) Lammertsma K., von Rague Schleyer P., Schwarz H. Angew. Chem. Int. Ed. Engl. 28:1989;1321.
11. Büchner M., Nixdorf A., Grützmacher H.-F. Chem. Eur. J. 4:1998;1799.
12. Nixdorf A., Grützmacher H.-F. Chem. Eur. J. 7:2001;1248.
13. All thermochemical data (if not stated otherwise) were taken from NIST Chemistry Webbook, NIST Standard Reference Database Number 69 - August 2001 Available: http://webbook.nist.gov./chemistry/.
14. Allemann M., Kellerhals H., Wanczek K.P. Int. J. Mass Spectrom. Ion Phys. 91:1983;139.
15. Caravatti P., Allemann M. Org. Mass Spectrom. 26:1991;514.
16. Kofel P., Allemann M., Kellerhals H., Wanczek K.P. Int. J. Mass Spectrom. Ion Phys. 65:1985;97.
17. Thölmann D., Grützmacher H.-F. J. Am. Chem. Soc. 113:1991;3281.
18. Bartmess J.E., Georgiadis R.M. Vacuum. 33:1983;149.
19. Anicich V.G. J. Phys. Chem. Ref. Data. 22:1993;1506.
20. Microcal Origin 4.1, Microcal Software Inc., Northampton, MA, USA, 1996.
21. Su T., Chesnavich W.J. J. Chem. Phys. 76:1982;5183.
22. M.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, A.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, A.G. Baboul, 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, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, J.L. Andres, C. Gonzalez, M. Head-Gordon, E.S. Replogle, J.A. Pople, GAUSSIAN 98, Revision A.9, Gaussian, Inc., Pittsburgh PA, 1998.
23. (a) McMahon T.B., Beauchamp J.J. J. Phys. Chem. 81:1977;593 (b) Jones E.G., Harrison A.G. Can. J. Chem. 45:1967;3119.
24. (a) McMahon T.B., Beauchamp J.J. J. Phys. Chem. 81:1977;593 (b) Jones E.G., Harrison A.G. Can. J. Chem. 45:1967;3119.
25. Nixdorf A., Grützmacher H.-F. J. Am. Chem. Soc. 119:1997;544.
26. Lalevée J., Allonas X., Fouassier X.J.-P. J. Am. Chem. Soc. 124:2002;9613.
27. Nixdorf A., Grützmacher H.-F. Eur. Mass Spectrom. 5:1999;93.
28. Thölmann D., Grützmacher H.-F. Int. J. Mass Spectrom. Ion Process. 117:1992;415.
29. Wong M.W., Radom L. J. Phys. Chem. A. 102:1998;2237.
30. Yates B.F., Radom L. Org. Mass Spectrom. 22:1987;430.
31. (a) Pross A., Shaik S.S. Acc. Chem. Res. 16:1983;363 (b) Shaik S.S., Pross A. J. Am. Chem. Soc. 111:1989;4306 (c) Cho J.K., Shaik S.S. J. Am. Chem. Soc. 113:1991;9890 (d) Shaik S., Shurki A. Angew. Chem. Int. Ed. Engl. 38:1999;586.
32. (a) Pross A., Shaik S.S. Acc. Chem. Res. 16:1983;363 (b) Shaik S.S., Pross A. J. Am. Chem. Soc. 111:1989;4306 (c) Cho J.K., Shaik S.S. J. Am. Chem. Soc. 113:1991;9890 (d) Shaik S., Shurki A. Angew. Chem. Int. Ed. Engl. 38:1999;586.
33. (a) Pross A., Shaik S.S. Acc. Chem. Res. 16:1983;363 (b) Shaik S.S., Pross A. J. Am. Chem. Soc. 111:1989;4306 (c) Cho J.K., Shaik S.S. J. Am. Chem. Soc. 113:1991;9890 (d) Shaik S., Shurki A. Angew. Chem. Int. Ed. Engl. 38:1999;586.
34. (a) Pross A., Shaik S.S. Acc. Chem. Res. 16:1983;363 (b) Shaik S.S., Pross A. J. Am. Chem. Soc. 111:1989;4306 (c) Cho J.K., Shaik S.S. J. Am. Chem. Soc. 113:1991;9890 (d) Shaik S., Shurki A. Angew. Chem. Int. Ed. Engl. 38:1999;586.
35. (a) Zipse H. Angew. Chem. Int. Ed. Engl. 36:1997;1697 (b) Schröder D., Trage C., Schwarz H., Danovich D., Shaik S. Int. J. Mass Spectrom. 200:2000;163.
36. (a) Zipse H. Angew. Chem. Int. Ed. Engl. 36:1997;1697 (b) Schröder D., Trage C., Schwarz H., Danovich D., Shaik S. Int. J. Mass Spectrom. 200:2000;163.