A specific gas phase substitution reaction between enol radical cations and t-butyl nitrite

[en] Ion-molecule reactions between ionized carbonyl compounds or ionized enols with t-butyl nitrite allow a clear-cut distinction to be made between both these isomeric structures. The most relevant difference between the observed reactions is the formal subs

Disciplines :

Chemistry

Author, co-author :

Gerbaux, Pascal

Wantier, Pascale

Nam, Pham-Cam

Nguyen, Minh Tho

Bouchoux, Guy

Flammang, Robert

Language :

English

Title :

A specific gas phase substitution reaction between enol radical cations and t-butyl nitrite

Publication date :

01 January 2004

Journal title :

European Journal of Mass Spectrometry

ISSN :

1469-0667

Publisher :

IM Publications, United Kingdom

Volume :

Issue :

Pages :

889 - 898

Peer reviewed :

Peer Reviewed verified by ORBi

Research unit :

S836 - Synthèse et spectrométrie de masse organiques

Available on ORBi UMONS :

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Bibliography

See for example: (a) J.L. Holmes and J.K. Terlouw, "The scope of metastable peak observations", Org. Mass Spectrom. 15, 383 (1980); (b) J.L. Holmes, "Ion structures, Neutral structures; Explorations in Mass Spectrometry", Adv. Mass Spectrom. 11, 53 (1988); (c) J.L. Holmes and P. Mayer, "A combined mass spectrometric and thermochemical examination of the C2H2N family of cations and radicals", J. Phys. Chem. 99, 1366 (1995); (d) D.V. Zagorevskii, J.-M. Regimbai and J.L. Holmes, "A tandem mass spectrometry study of [C6H5O] ions", Int. J. Mass Spectrom. Ion Proc. 160, 211 (1997); (e) D.V. Zagorevskii and J.L. Holmes, "The heat of formation of the [C 6H5O] isomeric ions, protonated 6-oxafulvalene", Int. J. Mass Spectrom. Ion Proc. 167/168, 231 (1997); (f) J. Cao, C. Aubry and J.L. Holmes, "Proton affinities of simple amines: entropies and enthalpies of activation and their effect on the kinetic method for evaluating proton affinities", J. Phys. Chem. A 104, 10045 (2000); (g) C. Aubry and J.L. Holmes, "The behavior of oxygen as a collision-induced dissociation target gas", J. Am. Soc. Mass Spectrom. 12, 23 (2000).
See for example: (a) J.L. Holmes and J.K. Terlouw, "The scope of metastable peak observations", Org. Mass Spectrom. 15, 383 (1980); (b) J.L. Holmes, "Ion structures, Neutral structures; Explorations in Mass Spectrometry", Adv. Mass Spectrom. 11, 53 (1988); (c) J.L. Holmes and P. Mayer, "A combined mass spectrometric and thermochemical examination of the C2H2N family of cations and radicals", J. Phys. Chem. 99, 1366 (1995); (d) D.V. Zagorevskii, J.-M. Regimbai and J.L. Holmes, "A tandem mass spectrometry study of [C6H5O] ions", Int. J. Mass Spectrom. Ion Proc. 160, 211 (1997); (e) D.V. Zagorevskii and J.L. Holmes, "The heat of formation of the [C 6H5O] isomeric ions, protonated 6-oxafulvalene", Int. J. Mass Spectrom. Ion Proc. 167/168, 231 (1997); (f) J. Cao, C. Aubry and J.L. Holmes, "Proton affinities of simple amines: entropies and enthalpies of activation and their effect on the kinetic method for evaluating proton affinities", J. Phys. Chem. A 104, 10045 (2000); (g) C. Aubry and J.L. Holmes, "The behavior of oxygen as a collision-induced dissociation target gas", J. Am. Soc. Mass Spectrom. 12, 23 (2000).
See for example: (a) J.L. Holmes and J.K. Terlouw, "The scope of metastable peak observations", Org. Mass Spectrom. 15, 383 (1980); (b) J.L. Holmes, "Ion structures, Neutral structures; Explorations in Mass Spectrometry", Adv. Mass Spectrom. 11, 53 (1988); (c) J.L. Holmes and P. Mayer, "A combined mass spectrometric and thermochemical examination of the C2H2N family of cations and radicals", J. Phys. Chem. 99, 1366 (1995); (d) D.V. Zagorevskii, J.-M. Regimbai and J.L. Holmes, "A tandem mass spectrometry study of [C6H5O] ions", Int. J. Mass Spectrom. Ion Proc. 160, 211 (1997); (e) D.V. Zagorevskii and J.L. Holmes, "The heat of formation of the [C 6H5O] isomeric ions, protonated 6-oxafulvalene", Int. J. Mass Spectrom. Ion Proc. 167/168, 231 (1997); (f) J. Cao, C. Aubry and J.L. Holmes, "Proton affinities of simple amines: entropies and enthalpies of activation and their effect on the kinetic method for evaluating proton affinities", J. Phys. Chem. A 104, 10045 (2000); (g) C. Aubry and J.L. Holmes, "The behavior of oxygen as a collision-induced dissociation target gas", J. Am. Soc. Mass Spectrom. 12, 23 (2000).
See for example: (a) J.L. Holmes and J.K. Terlouw, "The scope of metastable peak observations", Org. Mass Spectrom. 15, 383 (1980); (b) J.L. Holmes, "Ion structures, Neutral structures; Explorations in Mass Spectrometry", Adv. Mass Spectrom. 11, 53 (1988); (c) J.L. Holmes and P. Mayer, "A combined mass spectrometric and thermochemical examination of the C2H2N family of cations and radicals", J. Phys. Chem. 99, 1366 (1995); (d) D.V. Zagorevskii, J.-M. Regimbai and J.L. Holmes, "A tandem mass spectrometry study of [C6H5O] ions", Int. J. Mass Spectrom. Ion Proc. 160, 211 (1997); (e) D.V. Zagorevskii and J.L. Holmes, "The heat of formation of the [C 6H5O] isomeric ions, protonated 6-oxafulvalene", Int. J. Mass Spectrom. Ion Proc. 167/168, 231 (1997); (f) J. Cao, C. Aubry and J.L. Holmes, "Proton affinities of simple amines: entropies and enthalpies of activation and their effect on the kinetic method for evaluating proton affinities", J. Phys. Chem. A 104, 10045 (2000); (g) C. Aubry and J.L. Holmes, "The behavior of oxygen as a collision-induced dissociation target gas", J. Am. Soc. Mass Spectrom. 12, 23 (2000).
See for example: (a) J.L. Holmes and J.K. Terlouw, "The scope of metastable peak observations", Org. Mass Spectrom. 15, 383 (1980); (b) J.L. Holmes, "Ion structures, Neutral structures; Explorations in Mass Spectrometry", Adv. Mass Spectrom. 11, 53 (1988); (c) J.L. Holmes and P. Mayer, "A combined mass spectrometric and thermochemical examination of the C2H2N family of cations and radicals", J. Phys. Chem. 99, 1366 (1995); (d) D.V. Zagorevskii, J.-M. Regimbai and J.L. Holmes, "A tandem mass spectrometry study of [C6H5O] ions", Int. J. Mass Spectrom. Ion Proc. 160, 211 (1997); (e) D.V. Zagorevskii and J.L. Holmes, "The heat of formation of the [C 6H5O] isomeric ions, protonated 6-oxafulvalene", Int. J. Mass Spectrom. Ion Proc. 167/168, 231 (1997); (f) J. Cao, C. Aubry and J.L. Holmes, "Proton affinities of simple amines: entropies and enthalpies of activation and their effect on the kinetic method for evaluating proton affinities", J. Phys. Chem. A 104, 10045 (2000); (g) C. Aubry and J.L. Holmes, "The behavior of oxygen as a collision-induced dissociation target gas", J. Am. Soc. Mass Spectrom. 12, 23 (2000).
See for example: (a) J.L. Holmes and J.K. Terlouw, "The scope of metastable peak observations", Org. Mass Spectrom. 15, 383 (1980); (b) J.L. Holmes, "Ion structures, Neutral structures; Explorations in Mass Spectrometry", Adv. Mass Spectrom. 11, 53 (1988); (c) J.L. Holmes and P. Mayer, "A combined mass spectrometric and thermochemical examination of the C2H2N family of cations and radicals", J. Phys. Chem. 99, 1366 (1995); (d) D.V. Zagorevskii, J.-M. Regimbai and J.L. Holmes, "A tandem mass spectrometry study of [C6H5O] ions", Int. J. Mass Spectrom. Ion Proc. 160, 211 (1997); (e) D.V. Zagorevskii and J.L. Holmes, "The heat of formation of the [C 6H5O] isomeric ions, protonated 6-oxafulvalene", Int. J. Mass Spectrom. Ion Proc. 167/168, 231 (1997); (f) J. Cao, C. Aubry and J.L. Holmes, "Proton affinities of simple amines: entropies and enthalpies of activation and their effect on the kinetic method for evaluating proton affinities", J. Phys. Chem. A 104, 10045 (2000); (g) C. Aubry and J.L. Holmes, "The behavior of oxygen as a collision-induced dissociation target gas", J. Am. Soc. Mass Spectrom. 12, 23 (2000).
See for example: (a) J.L. Holmes and J.K. Terlouw, "The scope of metastable peak observations", Org. Mass Spectrom. 15, 383 (1980); (b) J.L. Holmes, "Ion structures, Neutral structures; Explorations in Mass Spectrometry", Adv. Mass Spectrom. 11, 53 (1988); (c) J.L. Holmes and P. Mayer, "A combined mass spectrometric and thermochemical examination of the C2H2N family of cations and radicals", J. Phys. Chem. 99, 1366 (1995); (d) D.V. Zagorevskii, J.-M. Regimbai and J.L. Holmes, "A tandem mass spectrometry study of [C6H5O] ions", Int. J. Mass Spectrom. Ion Proc. 160, 211 (1997); (e) D.V. Zagorevskii and J.L. Holmes, "The heat of formation of the [C 6H5O] isomeric ions, protonated 6-oxafulvalene", Int. J. Mass Spectrom. Ion Proc. 167/168, 231 (1997); (f) J. Cao, C. Aubry and J.L. Holmes, "Proton affinities of simple amines: entropies and enthalpies of activation and their effect on the kinetic method for evaluating proton affinities", J. Phys. Chem. A 104, 10045 (2000); (g) C. Aubry and J.L. Holmes, "The behavior of oxygen as a collision-induced dissociation target gas", J. Am. Soc. Mass Spectrom. 12, 23 (2000).
For selected reviews see: (a) S.A. McLuckey and J.M. Wells, "Mass analysis at the Advent of the 21st Century", Chem. Rev. 101, 571 (2001); (b) S. Gronert, "Mass Spectrometric studies of organic ion/molecule reactions", Chem. Rev. 101, 329 (2001); (c) K. Takashima and J.M. Riveros, "Gas-phase solvated negative ions", Mass Spectrom. Rev. 17, 409 (1998); (d) M.N. Eberlin, "Triple stage pentaquadrupole (QqQqQ) mass spectrometry and ion/molecule reactions", Mass Spectrom. Rev. 16, 113 (1997); (e) J.S. Brodbelt, "Analytical applications of ion-molecule reactions", Mass Spectrom. Rev. 16, 91 (1997).
For selected reviews see: (a) S.A. McLuckey and J.M. Wells, "Mass analysis at the Advent of the 21st Century", Chem. Rev. 101, 571 (2001); (b) S. Gronert, "Mass Spectrometric studies of organic ion/molecule reactions", Chem. Rev. 101, 329 (2001); (c) K. Takashima and J.M. Riveros, "Gas-phase solvated negative ions", Mass Spectrom. Rev. 17, 409 (1998); (d) M.N. Eberlin, "Triple stage pentaquadrupole (QqQqQ) mass spectrometry and ion/molecule reactions", Mass Spectrom. Rev. 16, 113 (1997); (e) J.S. Brodbelt, "Analytical applications of ion-molecule reactions", Mass Spectrom. Rev. 16, 91 (1997).
For selected reviews see: (a) S.A. McLuckey and J.M. Wells, "Mass analysis at the Advent of the 21st Century", Chem. Rev. 101, 571 (2001); (b) S. Gronert, "Mass Spectrometric studies of organic ion/molecule reactions", Chem. Rev. 101, 329 (2001); (c) K. Takashima and J.M. Riveros, "Gas-phase solvated negative ions", Mass Spectrom. Rev. 17, 409 (1998); (d) M.N. Eberlin, "Triple stage pentaquadrupole (QqQqQ) mass spectrometry and ion/molecule reactions", Mass Spectrom. Rev. 16, 113 (1997); (e) J.S. Brodbelt, "Analytical applications of ion-molecule reactions", Mass Spectrom. Rev. 16, 91 (1997).
For selected reviews see: (a) S.A. McLuckey and J.M. Wells, "Mass analysis at the Advent of the 21st Century", Chem. Rev. 101, 571 (2001); (b) S. Gronert, "Mass Spectrometric studies of organic ion/molecule reactions", Chem. Rev. 101, 329 (2001); (c) K. Takashima and J.M. Riveros, "Gas-phase solvated negative ions", Mass Spectrom. Rev. 17, 409 (1998); (d) M.N. Eberlin, "Triple stage pentaquadrupole (QqQqQ) mass spectrometry and ion/molecule reactions", Mass Spectrom. Rev. 16, 113 (1997); (e) J.S. Brodbelt, "Analytical applications of ion-molecule reactions", Mass Spectrom. Rev. 16, 91 (1997).
For selected reviews see: (a) S.A. McLuckey and J.M. Wells, "Mass analysis at the Advent of the 21st Century", Chem. Rev. 101, 571 (2001); (b) S. Gronert, "Mass Spectrometric studies of organic ion/molecule reactions", Chem. Rev. 101, 329 (2001); (c) K. Takashima and J.M. Riveros, "Gas-phase solvated negative ions", Mass Spectrom. Rev. 17, 409 (1998); (d) M.N. Eberlin, "Triple stage pentaquadrupole (QqQqQ) mass spectrometry and ion/molecule reactions", Mass Spectrom. Rev. 16, 113 (1997); (e) J.S. Brodbelt, "Analytical applications of ion-molecule reactions", Mass Spectrom. Rev. 16, 91 (1997).
For examples, see: (a) M.A. Trikoupis, P. Gerbaux, D.J. Lavorato, R. Flammang and J.K. Terlouw, "The generation of H-shift isomers of hydroxypyridine: a combined experimental and computational investigation", Int. J. Mass Spectrom. 217, 1 (2002); (b) P. Gerbaux, J.Y. Salpin, G. Bouchoux and R. Flammang. "Thiosulfoxides (X2S = S) and Disulfanes (XSSX): First Observation of Organic Thiosulfoxides", Int. J. Mass Spectrom. 195/196, 239 (2000); (c) L.A.B. Moraes, M.N. Eberlin and K.K. Laali, "Gas phase synthesis and characterization of an azaphosphirenium ion: the first N,P-analogue of the aromatic cyclopropenyl cation", Organometallics 20, 4863 (2001); (d) C. Petucci, L. Guler and H.I. Kenttamaa, "Differentiation of stereoisomeric steroids by reactions with phosphenium ions", J. Am. Soc. Mass Spectrom. 13, 362 (2002); (e) S. Gronert and R. Huang, "A strong preference for a salt-bridge structure in the gas phase: reactions of deprotonated amino acids with borane", J. Am. Chem. Soc. 123, 8606 (2001); (f) P. Gerbaux, M. Barbieux-Flammang, Y. Van Haverbeke and R. Flammang, "Characterization of ionized heterocyclic carbenes by ion-molecule reactions", Rapid Commun. Mass Spectrom. 13, 1707 (1999); (g) H.I. Kenttamaa, "Long-lived distonic radical cations", Org. Mass Spectrom. 29, 1 (1994).
For examples, see: (a) M.A. Trikoupis, P. Gerbaux, D.J. Lavorato, R. Flammang and J.K. Terlouw, "The generation of H-shift isomers of hydroxypyridine: a combined experimental and computational investigation", Int. J. Mass Spectrom. 217, 1 (2002); (b) P. Gerbaux, J.Y. Salpin, G. Bouchoux and R. Flammang. "Thiosulfoxides (X2S = S) and Disulfanes (XSSX): First Observation of Organic Thiosulfoxides", Int. J. Mass Spectrom. 195/196, 239 (2000); (c) L.A.B. Moraes, M.N. Eberlin and K.K. Laali, "Gas phase synthesis and characterization of an azaphosphirenium ion: the first N,P-analogue of the aromatic cyclopropenyl cation", Organometallics 20, 4863 (2001); (d) C. Petucci, L. Guler and H.I. Kenttamaa, "Differentiation of stereoisomeric steroids by reactions with phosphenium ions", J. Am. Soc. Mass Spectrom. 13, 362 (2002); (e) S. Gronert and R. Huang, "A strong preference for a salt-bridge structure in the gas phase: reactions of deprotonated amino acids with borane", J. Am. Chem. Soc. 123, 8606 (2001); (f) P. Gerbaux, M. Barbieux-Flammang, Y. Van Haverbeke and R. Flammang, "Characterization of ionized heterocyclic carbenes by ion-molecule reactions", Rapid Commun. Mass Spectrom. 13, 1707 (1999); (g) H.I. Kenttamaa, "Long-lived distonic radical cations", Org. Mass Spectrom. 29, 1 (1994).
For examples, see: (a) M.A. Trikoupis, P. Gerbaux, D.J. Lavorato, R. Flammang and J.K. Terlouw, "The generation of H-shift isomers of hydroxypyridine: a combined experimental and computational investigation", Int. J. Mass Spectrom. 217, 1 (2002); (b) P. Gerbaux, J.Y. Salpin, G. Bouchoux and R. Flammang. "Thiosulfoxides (X2S = S) and Disulfanes (XSSX): First Observation of Organic Thiosulfoxides", Int. J. Mass Spectrom. 195/196, 239 (2000); (c) L.A.B. Moraes, M.N. Eberlin and K.K. Laali, "Gas phase synthesis and characterization of an azaphosphirenium ion: the first N,P-analogue of the aromatic cyclopropenyl cation", Organometallics 20, 4863 (2001); (d) C. Petucci, L. Guler and H.I. Kenttamaa, "Differentiation of stereoisomeric steroids by reactions with phosphenium ions", J. Am. Soc. Mass Spectrom. 13, 362 (2002); (e) S. Gronert and R. Huang, "A strong preference for a salt-bridge structure in the gas phase: reactions of deprotonated amino acids with borane", J. Am. Chem. Soc. 123, 8606 (2001); (f) P. Gerbaux, M. Barbieux-Flammang, Y. Van Haverbeke and R. Flammang, "Characterization of ionized heterocyclic carbenes by ion-molecule reactions", Rapid Commun. Mass Spectrom. 13, 1707 (1999); (g) H.I. Kenttamaa, "Long-lived distonic radical cations", Org. Mass Spectrom. 29, 1 (1994).
For examples, see: (a) M.A. Trikoupis, P. Gerbaux, D.J. Lavorato, R. Flammang and J.K. Terlouw, "The generation of H-shift isomers of hydroxypyridine: a combined experimental and computational investigation", Int. J. Mass Spectrom. 217, 1 (2002); (b) P. Gerbaux, J.Y. Salpin, G. Bouchoux and R. Flammang. "Thiosulfoxides (X2S = S) and Disulfanes (XSSX): First Observation of Organic Thiosulfoxides", Int. J. Mass Spectrom. 195/196, 239 (2000); (c) L.A.B. Moraes, M.N. Eberlin and K.K. Laali, "Gas phase synthesis and characterization of an azaphosphirenium ion: the first N,P-analogue of the aromatic cyclopropenyl cation", Organometallics 20, 4863 (2001); (d) C. Petucci, L. Guler and H.I. Kenttamaa, "Differentiation of stereoisomeric steroids by reactions with phosphenium ions", J. Am. Soc. Mass Spectrom. 13, 362 (2002); (e) S. Gronert and R. Huang, "A strong preference for a salt-bridge structure in the gas phase: reactions of deprotonated amino acids with borane", J. Am. Chem. Soc. 123, 8606 (2001); (f) P. Gerbaux, M. Barbieux-Flammang, Y. Van Haverbeke and R. Flammang, "Characterization of ionized heterocyclic carbenes by ion-molecule reactions", Rapid Commun. Mass Spectrom. 13, 1707 (1999); (g) H.I. Kenttamaa, "Long-lived distonic radical cations", Org. Mass Spectrom. 29, 1 (1994).
For examples, see: (a) M.A. Trikoupis, P. Gerbaux, D.J. Lavorato, R. Flammang and J.K. Terlouw, "The generation of H-shift isomers of hydroxypyridine: a combined experimental and computational investigation", Int. J. Mass Spectrom. 217, 1 (2002); (b) P. Gerbaux, J.Y. Salpin, G. Bouchoux and R. Flammang. "Thiosulfoxides (X2S = S) and Disulfanes (XSSX): First Observation of Organic Thiosulfoxides", Int. J. Mass Spectrom. 195/196, 239 (2000); (c) L.A.B. Moraes, M.N. Eberlin and K.K. Laali, "Gas phase synthesis and characterization of an azaphosphirenium ion: the first N,P-analogue of the aromatic cyclopropenyl cation", Organometallics 20, 4863 (2001); (d) C. Petucci, L. Guler and H.I. Kenttamaa, "Differentiation of stereoisomeric steroids by reactions with phosphenium ions", J. Am. Soc. Mass Spectrom. 13, 362 (2002); (e) S. Gronert and R. Huang, "A strong preference for a salt-bridge structure in the gas phase: reactions of deprotonated amino acids with borane", J. Am. Chem. Soc. 123, 8606 (2001); (f) P. Gerbaux, M. Barbieux-Flammang, Y. Van Haverbeke and R. Flammang, "Characterization of ionized heterocyclic carbenes by ion-molecule reactions", Rapid Commun. Mass Spectrom. 13, 1707 (1999); (g) H.I. Kenttamaa, "Long-lived distonic radical cations", Org. Mass Spectrom. 29, 1 (1994).
For examples, see: (a) M.A. Trikoupis, P. Gerbaux, D.J. Lavorato, R. Flammang and J.K. Terlouw, "The generation of H-shift isomers of hydroxypyridine: a combined experimental and computational investigation", Int. J. Mass Spectrom. 217, 1 (2002); (b) P. Gerbaux, J.Y. Salpin, G. Bouchoux and R. Flammang. "Thiosulfoxides (X2S = S) and Disulfanes (XSSX): First Observation of Organic Thiosulfoxides", Int. J. Mass Spectrom. 195/196, 239 (2000); (c) L.A.B. Moraes, M.N. Eberlin and K.K. Laali, "Gas phase synthesis and characterization of an azaphosphirenium ion: the first N,P-analogue of the aromatic cyclopropenyl cation", Organometallics 20, 4863 (2001); (d) C. Petucci, L. Guler and H.I. Kenttamaa, "Differentiation of stereoisomeric steroids by reactions with phosphenium ions", J. Am. Soc. Mass Spectrom. 13, 362 (2002); (e) S. Gronert and R. Huang, "A strong preference for a salt-bridge structure in the gas phase: reactions of deprotonated amino acids with borane", J. Am. Chem. Soc. 123, 8606 (2001); (f) P. Gerbaux, M. Barbieux-Flammang, Y. Van Haverbeke and R. Flammang, "Characterization of ionized heterocyclic carbenes by ion-molecule reactions", Rapid Commun. Mass Spectrom. 13, 1707 (1999); (g) H.I. Kenttamaa, "Long-lived distonic radical cations", Org. Mass Spectrom. 29, 1 (1994).
For examples, see: (a) M.A. Trikoupis, P. Gerbaux, D.J. Lavorato, R. Flammang and J.K. Terlouw, "The generation of H-shift isomers of hydroxypyridine: a combined experimental and computational investigation", Int. J. Mass Spectrom. 217, 1 (2002); (b) P. Gerbaux, J.Y. Salpin, G. Bouchoux and R. Flammang. "Thiosulfoxides (X2S = S) and Disulfanes (XSSX): First Observation of Organic Thiosulfoxides", Int. J. Mass Spectrom. 195/196, 239 (2000); (c) L.A.B. Moraes, M.N. Eberlin and K.K. Laali, "Gas phase synthesis and characterization of an azaphosphirenium ion: the first N,P-analogue of the aromatic cyclopropenyl cation", Organometallics 20, 4863 (2001); (d) C. Petucci, L. Guler and H.I. Kenttamaa, "Differentiation of stereoisomeric steroids by reactions with phosphenium ions", J. Am. Soc. Mass Spectrom. 13, 362 (2002); (e) S. Gronert and R. Huang, "A strong preference for a salt-bridge structure in the gas phase: reactions of deprotonated amino acids with borane", J. Am. Chem. Soc. 123, 8606 (2001); (f) P. Gerbaux, M. Barbieux-Flammang, Y. Van Haverbeke and R. Flammang, "Characterization of ionized heterocyclic carbenes by ion-molecule reactions", Rapid Commun. Mass Spectrom. 13, 1707 (1999); (g) H.I. Kenttamaa, "Long-lived distonic radical cations", Org. Mass Spectrom. 29, 1 (1994).
H. Gao, C.J. Petzold, M.D. Leavelland J.A. Leary, "Investigation of ion/molecule reactions as a quantification method for phosphorylated positional isomers: an FT-ICR approach", J. Am. Soc. Mass Spectrom. 14, 916 (2003) and references cited herein.
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http://webbook.nist.gov/chemistry/
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