Gas phase ion chemistry of the heterocyclic isomers 3-methyl-1,2- benzisoxazole and 2-methyl-1,3-benzoxazole

Journal of the American Society for Mass Spectrometry

Volumn 15, Issue 7, 2004, Pages 1005-1013

  Giorgi, Gianluca ^a   Salvini, Laura ^a   Ponticelli, Fabio ^a  

^a UNIVERSITY OF SIENA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIC ISOMERS; ISOMERIC ION STRUCTURES;

BENZENE; CARBON MONOXIDE; ISOMERS; ISOTOPES;

MASS SPECTROMETRY;

CARBON MONOXIDE; HETEROCYCLIC COMPOUND; OXAZOLE DERIVATIVE;

AB INITIO CALCULATION; ARTICLE; ATOM; COLLISIONALLY ACTIVATED DISSOCIATION; DECOMPOSITION; GAS ANALYSIS; ISOMERIZATION; ISOTOPE LABELING; MASS SPECTROMETRY; MOLECULAR INTERACTION; PHASE SEPARATION; PHYSICAL CHEMISTRY; STRUCTURE ANALYSIS; THEORETICAL STUDY;

EID: 3242712460     PISSN: 10440305     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jasms.2004.04.002     Document Type: Article

References (33)

1. Cooks R.G., Beynon J.H., Caprioli R.M., Lester G.R. Metastable Ions. 1973;Elsevier Scientific, Amsterdam, The Netherlands
2. Bush K.L., Glish G.L., McLuckey S.A. Mass Spectrometry/Mass Spectrometry Techniques and Applications of Tandem Mass Spectrometry. 1988;VCH, New York, NY
3. Porter Q.N. Mass Spectrometry of Heterocyclic Compounds. 2nd ed:1985;848-892 J. Wiley and Sons, New York, NY. and references therein
4. Reichen W. The Thermal Benzoxazinone-Benzoxazole Conversion, a Reexecution of a Mass Spectrometric Decay by Thermolysis. Helv. Chim. Acta. 60:1977;186-190
5. Tsiamis C., Tsoungas P.G. The Electron-Impact Mass Spectra of 1,2-Benzisoxazoles N-Oxides. J. Heterocyclic Chem. 22:1985;687-691
6. Dyall L.K., Karpa G.J. Mass Spectra of 3-Phenyl-2,1-Benzisoxazoles. Org. Mass Spectrom. 24:1989;70-73
7. Guarna A., Moneti G. Reactivity in the Gas Phase. Behavior of Isoxazoles under Negative Ion Chemical Ionization Conditions. Org. Mass Spectrom. 24:1989;490-496
8. Cojocaru M., Hassner A., Maurya R. Mass Spectra of Isoxazolo[4,3-c]-N- Alkyl-Piperidine Derivatives. Org. Mass Spectrom. 26:1991;667-668
9. Flammang R., Plisnier M., Bouchoux G., Hoppilliard Y., Humbert S., Wentrup C. Unimolecular Chemistry of Oxazole and Isoxazole Radical Cations in the Gas Phase Combined Experimental and Molecular Orbital Study. Org. Mass Spectrom. 27:1992;317-325
10. Ullman E.F., Singh B. Photochemical Transposition of Ring Atoms in Five-Membered Heterocycles. The Photorearrangement of 3,5-Diphenylisoxazole. J. Am. Chem. Soc. 88:1966;1844-1845
11. Nakata H., Sakurai H., Yoshizumi H., Tatematsu A. The Primary Fragmentation Step of Isoxazole upon Electron Impact. A Correlation with Photochemistry. Org. Mass Spectrom. 1:1968;199-204
12. Ponticelli F., Giomi D., Papaleo S., Tedeschi P. Mass Spectra of Aromatic 3-Methylisoxazolo- and 2-Methyloxazolopyridines. Org. Mass Spectrom. 28:1993;451-454
13. Lozynski M., Krzyzanowska E., Matecka D. Mass Spectra of Some Dialkylbenz-Oxazoles and 1,2-Benzisoxazoles. Polish J. Chem. 64:1990;93-99
14. Maquestiau A., Van Haverbeke Y., De Meyer C., Flammang R. Isomerisation du Benzoxazole et de l'Anthranile sous l'Impact Electronique. Org. Mass Spectrom. 9:1974;149-151
15. Selva A., Vettori U., Gaetani E. Mass Spectrometry of Heterocycles Compounds. VII Evidence for Common Structure(s) of 1,2-Benzoisothiazole and Benzothiazole Molecular Ions Produced by Electron Impact. Org. Mass Spectrom. 9:1974;1161-1165
16. Giorgi G., Anzini M., Cappelli A., Corelli F., Vomero S. Characterization and Differentiation of Heterocyclic Isomers. Part 2. Mass Spectrometry and Molecular Orbital Calculations on Pyrrolo[1,2-a][1,4] benzodiazepin-4-one, -6-one, -4,6-dione. J. Am. Soc. Mass Spectrom. 7:1996;653-663
17. Giorgi G., Salvini L., Ponticelli F., Tedeschi P. Characterization and Differentiation of Heterocyclic Isomers. Part 3. Study of High Internal Energy Ions Produced by Electron Ionization Mass Spectrometry on Methyl-1,2- and Methyl-1,3-Thiazolopyridines. J. Heterocyclic Chem. 33:1996;1895-1902
18. Giorgi G., Salvini L., Ponticelli F. Structural Characterization and Regiochemical Differentiation of Modified Isomeric Tryptophans. J. Am. Soc. Mass Spectrom. 13:2002;1298-1303
19. Da Silva M., Perlat M.C., Tabet J.C., Giorgi G., Salvini L., Ponticelli F. Application of Self-Ionization for Enhancing Stereochemical and Positional Effects from Arylglycosides Under Electron Ionization Conditions in an Ion Trap Mass Spectrometer. J. Am. Soc. Mass Spectrom. 14:2003;851-861
20. Giorgi, G., Salvini, L., Ponticelli, F. Gas Phase Reactivity of Isomeric Arylglycosides Towards Amines. Chemical Ionization Mass Spectrometry and Tandem Mass Spectrometry Study. J. Am. Soc. Mass Spectrom. 2004, 15, 244-252
21. Giorgi G., Ponticelli F., Czira G., Vékey K. Characterization and Differentiation of Heterocyclic Isomers. Tandem Mass Spectrometry and Molecular Orbital Calculations on 3-Methylisoxazolo- and 2-Methyloxazolopyridines. J. Am. Soc. Mass Spectrom. 6:1995;962-971
22. Giorgi G. Characterization and Differentiation of Heterocyclic Isomers. Part 5. About Mass Spectra and Library Entries of Benz(is)oxazoles. J. Mass Spectrom. 33:1998;1033-1036
23. The Chemistry of Heterocyclic Compounds, Vol. XLIX. Grünanger P., Vita-Finzi. Isoxazoles, Part 1. 1991;J. Wiley and Sons, New York, NY
24. The Chemistry of Heterocyclic Compounds Vol. XLIX. Grünanger P., Vita-Finzi. 1,2-Benzisoxazoles, Part Two. 1999;J. Wiley and Sons, New York, NY
25. Casini G., Gualtieri F., Stein M.L. On 1,2-Benzisoxazole-3-Acetic Acid and 3-Methyl-1,2-Benisoxazole A Restatement. J. Heterocyclic Chem. 6:1979;279-283
26. De Luca M.R., Kerwin S.M. The para-Toluenesulfonic Acid-Promoted Synthesis of 2-Substituted Benzoxazoles and Benzimidazoles from Diacylated Precursors. Tetrahedron. 53:1997;457-464
27. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Rega, N.; Salvador, P.; Dannenberg, J. J.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Revision A.11.3; Gaussian, Inc.: Pittsburgh, PA, 2002
28. Becke A.D. Density-Functional Thermochemistry. III. The Role of Exact Exchange. J. Chem. Phys. 98:1993;5648-5652
29. Schmidt M.W., Baldridge K.K., Boatz J.A., Elbert S.T., Gordon M.S., Jensen J.H., Koseki S., Matsunaga N., Nguyen K.A., Su S.J., Windus T.L., Dupuis M., Montgomery J.A. The General Atomic and Molecular Electronic Structure System. J. Comp. Chem. 14:1993;1347-1363
30. Ohashi M., Tsujimoto K., Yoshino A., Yonezawa T. Mass Spectra of Benzotriazoles. Correlation with Thermolytic and Photolytic Fragmentations. Org. Mass Spectrom. 4:1970;203-210
31. Palmer M.H., Russell E.R.R., Wolstenholme W.A. The Mass Spectra of Cinnolines and Their N-Oxides. Org. Mass Spectrom. 2:1969;1265-1275
32. Doppler T., Schmid H., Hansen H.-J. Zur Photochemie von 1,2-Benzisoxazolen in Stark Saurer Lösung. Helv. Chim. Acta. 62:1979;314-325
33. Chase, M. W. Jr. NIST-JANAF Themochemical Tables, 4th ed. J. Phys. Chem. Ref. Data Monograph 9. 1998, 1-1951