The first nonclassical distonic ion

Journal of the American Chemical Society

Volumn 122, Issue 32, 2000, Pages 7776-7780

  Gozzo, Fabio C ^a   Moraes, Luiz Alberto B ^a   Eberlin, Marcos N ^a   Laali, Kenneth K ^b  

^a UNIVERSITY OF CAMPINAS   (Brazil)

^b KENT STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL DERIVATIVE; FREE RADICAL; ORGANOPHOSPHORUS COMPOUND;

ARTICLE; ENERGY; ENTHALPY; IONIZATION; KINETICS; MASS SPECTROMETRY; MOLECULAR INTERACTION;

EID: 0034675005     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja993749m     Document Type: Article

References (60)

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11. For reviews on distonic ions see: (a) Hammerum, S. Mass Spectrom. Rev. 1988, 7, 123. (b) Bouchoux, G. Mass Spectrom. Rev. 1988, 7, 203. (c) Stirk, K. M.; Kiminkinen, M. L. K.; Kenttämaa, H. I. Chem. Rev. 1992, 92, 1649.
12. For reviews on distonic ions see: (a) Hammerum, S. Mass Spectrom. Rev. 1988, 7, 123. (b) Bouchoux, G. Mass Spectrom. Rev. 1988, 7, 203. (c) Stirk, K. M.; Kiminkinen, M. L. K.; Kenttämaa, H. I. Chem. Rev. 1992, 92, 1649.
13. For a review on the formation and reactivity of distonic ions in condensed phase see ref 4a. For examples on the rich gas-phase chemistry of distonic ions see ref 4; for more recent examples see: (a) Yu, S. J.; Holliman, C. L.; Rempel, D. L.; Gross, M. L. J. Am. Chem. Soc. 1993, 115, 9676. (b) Wesdemiotis, C.; Polce, M. J. Rapid Commun. Mass Spectrom. 1996, 10, 235. (c) Thoen, K. K.; Smith, R. L.; Nousiainen, J. J.; Nelson, E. D.; Kenttämaa, H. I. J. Am. Chem. Soc. 1996, 118, 8669. (d) Flammang, R.; Gerbaux, P.; Nguyen, M. T.; Salpin, J.-Y.; Bouchoux, G. J. Phys. Chem. A 1998, 102, 861. (e) Chou, P. K.; Thoen, K. K.; Kenttämaa, H. I. J. Org. Chem. 1998, 63, 4470. (f) Moraes, L. A. B.; Eberlin, M. N. J. Am. Chem. Soc. 1998, 120, 11136. (g) Thissen, R.; Mourgues, P.; Audier, H. E. Eur. Mass Spectrom. 1998, 4, 79. (h) Moraes, L. A. B.; Eberlin, M. N. J. Am. Soc. Mass Spectrom. 2000, 11, 697.
14. For a review on the formation and reactivity of distonic ions in condensed phase see ref 4a. For examples on the rich gas-phase chemistry of distonic ions see ref 4; for more recent examples see: (a) Yu, S. J.; Holliman, C. L.; Rempel, D. L.; Gross, M. L. J. Am. Chem. Soc. 1993, 115, 9676. (b) Wesdemiotis, C.; Polce, M. J. Rapid Commun. Mass Spectrom. 1996, 10, 235. (c) Thoen, K. K.; Smith, R. L.; Nousiainen, J. J.; Nelson, E. D.; Kenttämaa, H. I. J. Am. Chem. Soc. 1996, 118, 8669. (d) Flammang, R.; Gerbaux, P.; Nguyen, M. T.; Salpin, J.-Y.; Bouchoux, G. J. Phys. Chem. A 1998, 102, 861. (e) Chou, P. K.; Thoen, K. K.; Kenttämaa, H. I. J. Org. Chem. 1998, 63, 4470. (f) Moraes, L. A. B.; Eberlin, M. N. J. Am. Chem. Soc. 1998, 120, 11136. (g) Thissen, R.; Mourgues, P.; Audier, H. E. Eur. Mass Spectrom. 1998, 4, 79. (h) Moraes, L. A. B.; Eberlin, M. N. J. Am. Soc. Mass Spectrom. 2000, 11, 697.
15. For a review on the formation and reactivity of distonic ions in condensed phase see ref 4a. For examples on the rich gas-phase chemistry of distonic ions see ref 4; for more recent examples see: (a) Yu, S. J.; Holliman, C. L.; Rempel, D. L.; Gross, M. L. J. Am. Chem. Soc. 1993, 115, 9676. (b) Wesdemiotis, C.; Polce, M. J. Rapid Commun. Mass Spectrom. 1996, 10, 235. (c) Thoen, K. K.; Smith, R. L.; Nousiainen, J. J.; Nelson, E. D.; Kenttämaa, H. I. J. Am. Chem. Soc. 1996, 118, 8669. (d) Flammang, R.; Gerbaux, P.; Nguyen, M. T.; Salpin, J.-Y.; Bouchoux, G. J. Phys. Chem. A 1998, 102, 861. (e) Chou, P. K.; Thoen, K. K.; Kenttämaa, H. I. J. Org. Chem. 1998, 63, 4470. (f) Moraes, L. A. B.; Eberlin, M. N. J. Am. Chem. Soc. 1998, 120, 11136. (g) Thissen, R.; Mourgues, P.; Audier, H. E. Eur. Mass Spectrom. 1998, 4, 79. (h) Moraes, L. A. B.; Eberlin, M. N. J. Am. Soc. Mass Spectrom. 2000, 11, 697.
16. For a review on the formation and reactivity of distonic ions in condensed phase see ref 4a. For examples on the rich gas-phase chemistry of distonic ions see ref 4; for more recent examples see: (a) Yu, S. J.; Holliman, C. L.; Rempel, D. L.; Gross, M. L. J. Am. Chem. Soc. 1993, 115, 9676. (b) Wesdemiotis, C.; Polce, M. J. Rapid Commun. Mass Spectrom. 1996, 10, 235. (c) Thoen, K. K.; Smith, R. L.; Nousiainen, J. J.; Nelson, E. D.; Kenttämaa, H. I. J. Am. Chem. Soc. 1996, 118, 8669. (d) Flammang, R.; Gerbaux, P.; Nguyen, M. T.; Salpin, J.-Y.; Bouchoux, G. J. Phys. Chem. A 1998, 102, 861. (e) Chou, P. K.; Thoen, K. K.; Kenttämaa, H. I. J. Org. Chem. 1998, 63, 4470. (f) Moraes, L. A. B.; Eberlin, M. N. J. Am. Chem. Soc. 1998, 120, 11136. (g) Thissen, R.; Mourgues, P.; Audier, H. E. Eur. Mass Spectrom. 1998, 4, 79. (h) Moraes, L. A. B.; Eberlin, M. N. J. Am. Soc. Mass Spectrom. 2000, 11, 697.
17. For a review on the formation and reactivity of distonic ions in condensed phase see ref 4a. For examples on the rich gas-phase chemistry of distonic ions see ref 4; for more recent examples see: (a) Yu, S. J.; Holliman, C. L.; Rempel, D. L.; Gross, M. L. J. Am. Chem. Soc. 1993, 115, 9676. (b) Wesdemiotis, C.; Polce, M. J. Rapid Commun. Mass Spectrom. 1996, 10, 235. (c) Thoen, K. K.; Smith, R. L.; Nousiainen, J. J.; Nelson, E. D.; Kenttämaa, H. I. J. Am. Chem. Soc. 1996, 118, 8669. (d) Flammang, R.; Gerbaux, P.; Nguyen, M. T.; Salpin, J.-Y.; Bouchoux, G. J. Phys. Chem. A 1998, 102, 861. (e) Chou, P. K.; Thoen, K. K.; Kenttämaa, H. I. J. Org. Chem. 1998, 63, 4470. (f) Moraes, L. A. B.; Eberlin, M. N. J. Am. Chem. Soc. 1998, 120, 11136. (g) Thissen, R.; Mourgues, P.; Audier, H. E. Eur. Mass Spectrom. 1998, 4, 79. (h) Moraes, L. A. B.; Eberlin, M. N. J. Am. Soc. Mass Spectrom. 2000, 11, 697.
18. For a review on the formation and reactivity of distonic ions in condensed phase see ref 4a. For examples on the rich gas-phase chemistry of distonic ions see ref 4; for more recent examples see: (a) Yu, S. J.; Holliman, C. L.; Rempel, D. L.; Gross, M. L. J. Am. Chem. Soc. 1993, 115, 9676. (b) Wesdemiotis, C.; Polce, M. J. Rapid Commun. Mass Spectrom. 1996, 10, 235. (c) Thoen, K. K.; Smith, R. L.; Nousiainen, J. J.; Nelson, E. D.; Kenttämaa, H. I. J. Am. Chem. Soc. 1996, 118, 8669. (d) Flammang, R.; Gerbaux, P.; Nguyen, M. T.; Salpin, J.-Y.; Bouchoux, G. J. Phys. Chem. A 1998, 102, 861. (e) Chou, P. K.; Thoen, K. K.; Kenttämaa, H. I. J. Org. Chem. 1998, 63, 4470. (f) Moraes, L. A. B.; Eberlin, M. N. J. Am. Chem. Soc. 1998, 120, 11136. (g) Thissen, R.; Mourgues, P.; Audier, H. E. Eur. Mass Spectrom. 1998, 4, 79. (h) Moraes, L. A. B.; Eberlin, M. N. J. Am. Soc. Mass Spectrom. 2000, 11, 697.
19. For a review on the formation and reactivity of distonic ions in condensed phase see ref 4a. For examples on the rich gas-phase chemistry of distonic ions see ref 4; for more recent examples see: (a) Yu, S. J.; Holliman, C. L.; Rempel, D. L.; Gross, M. L. J. Am. Chem. Soc. 1993, 115, 9676. (b) Wesdemiotis, C.; Polce, M. J. Rapid Commun. Mass Spectrom. 1996, 10, 235. (c) Thoen, K. K.; Smith, R. L.; Nousiainen, J. J.; Nelson, E. D.; Kenttämaa, H. I. J. Am. Chem. Soc. 1996, 118, 8669. (d) Flammang, R.; Gerbaux, P.; Nguyen, M. T.; Salpin, J.-Y.; Bouchoux, G. J. Phys. Chem. A 1998, 102, 861. (e) Chou, P. K.; Thoen, K. K.; Kenttämaa, H. I. J. Org. Chem. 1998, 63, 4470. (f) Moraes, L. A. B.; Eberlin, M. N. J. Am. Chem. Soc. 1998, 120, 11136. (g) Thissen, R.; Mourgues, P.; Audier, H. E. Eur. Mass Spectrom. 1998, 4, 79. (h) Moraes, L. A. B.; Eberlin, M. N. J. Am. Soc. Mass Spectrom. 2000, 11, 697.
20. For a review on the formation and reactivity of distonic ions in condensed phase see ref 4a. For examples on the rich gas-phase chemistry of distonic ions see ref 4; for more recent examples see: (a) Yu, S. J.; Holliman, C. L.; Rempel, D. L.; Gross, M. L. J. Am. Chem. Soc. 1993, 115, 9676. (b) Wesdemiotis, C.; Polce, M. J. Rapid Commun. Mass Spectrom. 1996, 10, 235. (c) Thoen, K. K.; Smith, R. L.; Nousiainen, J. J.; Nelson, E. D.; Kenttämaa, H. I. J. Am. Chem. Soc. 1996, 118, 8669. (d) Flammang, R.; Gerbaux, P.; Nguyen, M. T.; Salpin, J.-Y.; Bouchoux, G. J. Phys. Chem. A 1998, 102, 861. (e) Chou, P. K.; Thoen, K. K.; Kenttämaa, H. I. J. Org. Chem. 1998, 63, 4470. (f) Moraes, L. A. B.; Eberlin, M. N. J. Am. Chem. Soc. 1998, 120, 11136. (g) Thissen, R.; Mourgues, P.; Audier, H. E. Eur. Mass Spectrom. 1998, 4, 79. (h) Moraes, L. A. B.; Eberlin, M. N. J. Am. Soc. Mass Spectrom. 2000, 11, 697.
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