Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Mass Spectroscopical Properties of Benzoyl Derivatives of Five-membered Monoheterocycles and Determination of Aromaticity Indices

  • Jeon, Kyu-Ok (Department of Chemistry, Kangwon National University) ;
  • Jun, Jung-Ho (Department of Chemistry, Kangwon National University) ;
  • Yu, Ji-Sook (Department of Chemistry, Kangwon National University) ;
  • Lee, Chang-Kiu (Department of Chemistry, Kangwon National University)
  • Published : 2004.12.20
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Abstract

The mass spectra of benzophenones, 2-benzoylthiophenes, 2-benzoylpyrroles, and 2-benzoylfurans which have substituents at the m- and p-positions of the benzoyl ring were analyzed to find correlations against the Hammett substituent parameter ${\sigma}\;and\;{\sigma}^+$. The slopes of the plots of the intensities of the fragments from the heterocycles against those of the benzene gave sets of meaningful values for the indices of aromaticity of the heterocycles: benzene 1.00; thiophene 0.94, pyrrole 0.82, and furan 0.74.

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References

  1. Cook, M. J.; Katritzky, A. R. Adv. Heterocyclic Chem. 1974,17, 255. https://doi.org/10.1016/S0065-2725(08)60910-1
  2. Simkin, B. Y.; Minkin, V. I.; Glukhovtsev, M. N. Adv.Heterocyclic Chem. 1993, 56, 303. https://doi.org/10.1016/S0065-2725(08)60196-8
  3. Katritzky, A. R.; Karelson,M.; Malhotra, N. Heterocycles 1991, 32, 127. https://doi.org/10.3987/REV-90-420
  4. Cordell, F. R.;Boggs, J. E. J. Mol. Struct. 1981, 85, 163. https://doi.org/10.1016/0166-1280(81)85059-2
  5. Bird, C. W.Tetrahedron 1985, 41, 1409. https://doi.org/10.1016/S0040-4020(01)96543-3
  6. Elvidge, J. A. Chem. Commun. 1965, 160.
  7. Julg, A.; Francois, P. Theor. Chim. Acta 1967, 8, 249. https://doi.org/10.1007/BF00527311
  8. Lee, C. K.; Yu, J. S.; Park, J. S. Bull. Korean Chem. Soc. 2000,21, 49.
  9. Lee, C. K.; Yu, J. S.; Lee, H.-J. J. Hererocyclic Chem.2002, 39, 1207. https://doi.org/10.1002/jhet.5570390615
  10. Lee, C. K.; Yu, J. S.; Ji, Y. R. J. HererocyclicChem. 2002, 39, 1219. https://doi.org/10.1002/jhet.5570390616
  11. Jeon, K. O.; Jun, J. H.; Yu, J. S.; Lee, C.K. J. Hererocyclic Chem. 2003, 40, 763. https://doi.org/10.1002/jhet.5570400504
  12. Jeon, K. O.; Yu, J. S.;Lee, C. K. Hererocycles 2003, 60, 2685. https://doi.org/10.3987/COM-03-9889
  13. Craik, D. J.; Brownlee, R. T. C. Prog. Phys. Org. Chem. 1983,14, 1. https://doi.org/10.1002/9780470171936.ch1
  14. Ehrenson, S.; Brownlee, R. T. C.; Taft, R. W. Prog.Phys. Org. Chem. 1973, 10, 1. https://doi.org/10.1002/9780470171899.ch1
  15. Bentley, T. W.; Johnstone, R. A. W.; Payling, D. W. J. Am. Chem.Soc. 1969, 91, 3978. https://doi.org/10.1021/ja01042a066
  16. McLafferty, F. W. Interpretation of Mass Spectra; W. A. Benjamin,Inc.: Massachusetts, U. S. A., 1973; pp 127 and 207-211.
  17. Bursey, M. M.; McLafferty, F. W. J. Am. Chem. Soc. 1966, 88,529. https://doi.org/10.1021/ja00955a026
  18. Howe, I.; Williams, D. H. J. Am. Chem. Soc. 1969, 91, 7137. https://doi.org/10.1021/ja01053a041
  19. Fiorenza, M.; Ricci, A.; Sbrena, G.; Pirazzini, G.; Eaborn, C.;Stamper, J. G. J. Chem. Soc. Perkin Trans. II 1978, 1232.
  20. McLafferty, F. W.; Wachs, T.; Lifshitz, C.; Innorta, G.; Irving, P. J.Am. Chem. Soc. 1970, 92, 6867. https://doi.org/10.1021/ja00726a025

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