Abstract
In the electron resonance capture mass spectra of phenol, anisole, thioanisole, and their fluorinated analogs the resonances above 3.8 eV are electronically excited Fischbach resonances due to the excitation of the electron from several occupied MOs to one unoccupied MO. The mechanisms of the formation of the negative ions for these compounds are identical and do not depend on the nature of the heteroatoms. The low-energy resonances in the second energy region for PhR compounds (R=OH, OMe, SMe) correlate with the positions of the second singlet transitions. With thermal electron energies fluorinated anisoles are characterized by the formation of long-lived rearrangement ions. The absence of the rearrangement ion in fluorinated thioanisole can be explained by the energetically less favorable removal of the neutral CHF=S fragment compared with the CHF=0 fragment for fluorinated anisole.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
Literature cited
V. I. Khvostenko, I. Kh. Aminev, and V. S. Fal'ko, Teor. Éksp. Khim.,9, 519 (1973).
K. Jäger and A. Henglein, Z. Naturforsch.,21a, 1251 (1966).
H. Bock, G. Wagner, and J. Kroner, Chem. Ber.,105, 3850 (1972).
A. Schweig and N. Thon, Chem. Phys. Lett.,38, 482 (1976).
P. S. Dewar, E. Ernstbrunner, and J. R. Gilmore, Tetrahedron,30, 2455 (1974).
E. Tegeler, G. Wiech, and A. Faessler, J. Phys. B, Atom. Mol. Phys.,13, 4771 (1980).
J. P. Maier and D. W. Turner, J. Chem. Soc., Faraday Trans. 2,69, 521 (1973).
I. W. Serfary, J. Org. Chem.,37, 2651 (1972).
A. D. Baker, J. Chem. Soc. B, 22 (1968).
W. E. Wentworth, T. Limero, and E. C. M. Chen, J. Phys. Chem.,91, 241 (1987).
A. V. Gurevich, G. V. Karachentsev, V. N. Kondrat'ev, et al., Dissociation Energy of Chemical Bonds. Ionization Potentials and Electron Affinity [in Russian], Nauka, Moscow (1974), pp. 82, 87, 88.
O. G. Khvostenko, B. G. Zykov, and N. L. Asfandiyarov, Khim. Fiz.,4, 1366 (1985).
A. A. Tumanov, P. G. Sennikov, A. N. Egorochkin, et al., Zh. Obshch. Khim.,53, 766 (1983).
V. I. Khvostenko, Negative-Ion Mass Spectrometry in Organic Chemistry [in Russian], Nauka, Moscow (1981).
A. S. Vorob'ev, I. I. Furlei, A. Sh. Sultanov, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 7, 1518 (1989).
Author information
Authors and Affiliations
Additional information
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 1042–1048, May, 1990.
Rights and permissions
About this article
Cite this article
Burmistrov, E.A., Furlei, I.I., Sultanov, A.S. et al. Resonance capture of electrons and photoelectron spectroscopy of the molecules of substituted anisoles and thioanisoles. Russ Chem Bull 39, 930–936 (1990). https://doi.org/10.1007/BF00961685
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00961685