Ion-molecule reactions involving methyl isocyanide and methyl cyanide

European Journal of Mass Spectrometry

Volumn 13, Issue 6, 2007, Pages 385-395

  Dechamps, Noémie ^a   Flammang, Robert ^a   Boulvin, Michaël ^a   Lamote, Luc ^b   Gerbaux, Pascal ^a   Vu, Thi Ngan ^c   Minh, Tho Nguyen ^c  

^a UNIVERSITY OF MONS   (Belgium)

^b Waters SA   (Belgium)

^c UNIVERSITY OF LEUVEN   (Belgium)

Author keywords

Caffeine; Chemical ionization mass spectrometry; Ion molecule reactions; Ketenimine; Methyl cyanide; Methyl isocyanide

Indexed keywords

EID: 41149156887     PISSN: 14690667     EISSN: None     Source Type: Journal    
DOI: 10.1255/ejms.896     Document Type: Article

References (28)

1. S. Hammerum, "Distonic radical cations in gaseous and condensed phase", Mass Spectrom. Rev. 7, 123 (1988). doi: 10.1002/mas.1280070202
2. D.M. Tomazela, A.A. Sabino, R. Sparrapan, F.C. Gozzo and M.N. Eberlin, "Distonoid ions", J. Am. Soc. Mass Spectrom. 17, 1014 (2006). doi: 10.1016/j.jasms.2006.03.008
3. S.G. Lias, J.E. Bartmess, J.F. Liebmann, J.L. Holmes, R.D. Levin and W.G. Mallard, "Gas phase ion and neutral thermochemistry", J. Phys. Chem. Ref. Data 17, Supplement 1 (1998).
4. th edition.
5. N. Dechamps, R. Flammang, M. Boulvin, L. Lamote, P. Gerbaux, P.C. Nam and M.T. Nguyen, "Ion/molelcule reactions involving ionized toluene or ionized methyl benzoate and neutral methyl isocyanide", Int. J. Mass Spectrom., in press.
6. 2• of methyl benzoate radical cation by associative ion/molelcule reactions", Int. J. Mass Spectrom. 249/250, 484 (2006). doi: 10.1016/j.ijms.2005.10.014
7. H.K. Ervasti, K.J. Jobst, P.C. Burgers, P.J.A. Ruttinck and J.K. Terlouw, "The acrylonitrile dimer ion: a study of its dissociation via self-catalysis, self-protonation and cyclisation into the pyrimidine radical cation", Int. J. Mass Spectrom. 262, 88 (2007). doi: 10.1016/j.ijms.2006.10.013
8. R.H. Bateman, J. Brown, M. Lefevere, R. Flammang and Y. Van Haverbeke, "Applicaion in gaseous and neutral chemistry using a six-sector mass spectrometer", Int. J. Mass Spectrom. Ion Processes 115, 205 (1992). doi: 10.1016/0168-1176(92)85042-X
9. R. Flammang, Y. Van Haverbeke, C. Braybrook and J. Brown, "A new hybrid mass spectrometer for the investigation of ion/molelcule reactions", Rapid Commun. Mass Spectrom. 9, 795 (1995). doi: 10.1002/rcm.1290090916
10. 2S radical cations: application of tandem mass spectrometry methodologies", Int. J. Mass Spectrom. 263, 289 (2007). doi: 10.1016/j.ijms.2007.03.007
11. R.E. Schuster, J.E. Scott and J. Casanova Jr, "Methyl isocyanide", Org. Synth. 46, 75 (1966).
12. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.A. Montgomery, 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, F. 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, C. Gonzalez, M. Challacombe, P.M. Gill, B. Johnson, W. Chen, M.W. Wong, J.L. Andres, C. Gonzalez, M. Head-Gordon, E.S. Repogle, J.A. Pople, Gaussian 98, Revision A.6. Gaussian Inc.; Pittsburgh, PA, USA (1998).
13. H. Wincel, R.H. Fokkens and N.M.M. Nibbering, "On the rearrangement of the cyanomethyl cation from gaseous acetonitrile", Int. J. Mass Spectrom. Ion Processes 96, 321 (1990). doi: 10.1016/0168-1176(90) 85132-L
14. A. Maquestiau, Y. Van Haverbeke, R. Flammang and P. Meyrant, "Chemical ionization of some aromatic and aliphatic oximes", Org. Mass Spectrom. 15, 80 (1980). doi: 10.1002/oms.1210150206
15. + ions", Org. Mass Spectrom. 21, 681 (1986). doi: 10.1002/oms.1210211013
16. See for instance: P. Lawrence and J.T. Brenna, "Acetonitrile covalent adduct chemical ionization mass spectrometry for double bond localization in non-methylene-interrupted polyene fatty acid methyl esters", Anal. Chem. 78, 1312 (2006). doi: 10.1021/ac0516584
17. G.A. Gray, "Study of ion/molelcule reactions and reaction mechanisms in acetonitrile by ion cyclotron resonance", J. Am. Chem. Soc. 90, 6002 (1968). doi: 10.1021/ja01024a011
18. J. Koput, "Ab initio heat of formation and singlet-triplet splitting for cyanocarbene (HCCN) and isocyanocarbene (HCNC)", J. Phys. Chem. A 107, 4717 (2003). doi: 10.1021/jp027774h
19. (a) J.C Poutsma, S.D. Upshaw, R.R. Squires and P.G. Wenthold, "Absolute heat of formation and singlet-triplet splitting for HCCN", J. Phys. Chem. A 106, (2002) 1067 (2002); doi: 10.1021/jp013653q
20. - reveals the quasilinear triplet carbenes, HCCN and HCNC", J. Chem. Phys. 117, 4323 (2002). doi: 10.1063/1.1496473
21. 2]caffeine", J. Label. Comp. Rad. 36, 187 (1987);
22. (b) V. Ghilain, "Identification de molécules organiques réactives en spectrométrie de masse par neutralisation- réionisation", PhD Thesis, University of Mons-Hainaut, Belgium (1996).
23. P. Gerbaux, R. Flammang, M.T. Nguyen, J.Y. Salpin and G. Bouchoux, "Formation and cheracterization of acetonitrile N-methylide and N-methylketenimine radical cations in the gas phase", J. Phys. Chem. A 102, 861 (1998). doi: 10.1021/jp9724129
24. D. Schröder, C. Heinemann, H. Schwarz, J.N. Harvey, S. Dua, S.J. Blanksby and J.H. Bowie, "Ethylenedione: An intrinsically short-lived molecule", Chem. Eur. J. 4, 2550 (1998). doi: 10.1002/(SICI)1521-3765(19981204)4:12<2550::AID-CHEM2550>3.0.CO;2-E
25. R. Flammang, Y. Van Haverbeke, S. Laurent, M. Barbieux-Flammang, M.W. Wong and C. Wentrup, "Iminoethenone radical cation: tandem mass spectrometry and ab initio MO studies", J. Phys. Chem. 98, 5801 (1994). doi: 10.1021/j100074a002
26. + radical cations", Org. Mass Spectrom. 12, 196 (1977). doi: 10.1002/oms.1210120403
27. R.R. Corderman, P.R. LeBreton, S.E. Buttrill, A.D. Williamson, J.L. Beauchamp, "Photoionization and ion cyclotron resonance studies of the ion chemistry of ethylene oxide", J. Chem. Phys. 65, 4929 (1976). doi: 10.1063/1.432969
28. J. van Thuijl, K.J. Klebe and J.J. van Houte, "Fragmentation behaviour of 1-methylimidazole and 1-methylpyrazole upon electron impact", Org. Mass Spectrom. 7, 1165 (1973). doi: 10.1002/oms.1210071005