[en] Ion-molecule reactions involving methyl isocyanide and methyl cyanide have been performed in a new rf-only hexapole collision cell inserted in a large-scale tandem mass spectrometer. Beside protonation processes, N-methyl cyanogen ions (CH(3)N(+)CCN) and
Disciplines :
Chemistry
Author, co-author :
Dechamps, Noémie
Flammang, Robert
Boulvin, Michaël ; Université de Mons > Faculté des Sciences > Synthèse et spectrométrie de masse organiques
S. Hammerum, "Distonic radical cations in gaseous and condensed phase", Mass Spectrom. Rev. 7, 123 (1988). doi: 10.1002/mas.1280070202
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
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).
R.C. Wheast (Ed.), Handbook of chemistry and physics, CRC Press, Boca Raton Florida, USA 57th edition.
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.
N. Dechamps, R. Flammang, P. Gerbaux, P.C. Nam and M.T. Nguyen, "Characterization of a distonic isomer C6H5C +(OH)OCH2• 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
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
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
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
V. Ramesh, P. Nagi Reddy, R. Srikanth, K. Bhanuphrakash, R. Srinivas, R. Flammang, N. Dechamps and P. Gerbaux, "C2H2S radical cations: application of tandem mass spectrometry methodologies", Int. J. Mass Spectrom. 263, 289 (2007). doi: 10.1016/j.ijms.2007.03.007
R.E. Schuster, J.E. Scott and J. Casanova Jr, "Methyl isocyanide", Org. Synth. 46, 75 (1966).
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).
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
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
W. Heerma, M. Sarneel and G. Dijkstra, "Structure and formation of gaseous [C3H4N]+ ions", Org. Mass Spectrom. 21, 681 (1986). doi: 10.1002/oms.1210211013
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
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
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
(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
(b) M.R. Nimlos, G. Davico, C.M. Geise, P.G. Wenthold, W.C. Lineberger, S.J. Blanksby, C.M. Hadad, G.A. Petersson, G.B. Ellison, "Photoelectron spectroscopy of HCCN- and HCNC- reveals the quasilinear triplet carbenes, HCCN and HCNC", J. Chem. Phys. 117, 4323 (2002). doi: 10.1063/1.1496473
(a) A. Kenani, J-L. Bernier, J-P. Henichart, "Synthesis and EIMS fragmentation of [1,3-15N2] xanthine and [1,3- 15N2]caffeine", J. Label. Comp. Rad. 36, 187 (1987);
(b) V. Ghilain, "Identification de molécules organiques réactives en spectrométrie de masse par neutralisation- réionisation", PhD Thesis, University of Mons-Hainaut, Belgium (1996).
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
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
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
J. van Thuijl, J.J. van Houte, A. Maquestiau, R. Flammang and C. De Meyer, "The formation and structure of [C2H3N] •+ radical cations", Org. Mass Spectrom. 12, 196 (1977). doi: 10.1002/oms.1210120403
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
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