Abstract
It was shown that the intensity of the peak of the molecular ion in the mass spectra of dibenzo-18-crown-6 derivatives depends to a marked extent on the electronic properties of the substituents on the benzene ring. Fragmentation of the substituents is observed after the decomposition of the polyether ring. This permits the proposition that the preferred localization of the charge in the molecular ion and the fragment ions is on the oxygen-containing part of the molecule. The analysis of the mass spectra of benzo-substituted crown ethers renders possible the determination of substituents occurring in the aromatic part of the molecule and their steric position.
Similar content being viewed by others
Literature cited
A. V. Bogatskii, N. G. Luk'yanenko, Yu. A. Popkov, N. Yu. Nazarova, M. U. Mamina, and Z. A. Chernotkach, Dokl. Akad. Nauk SSSR,171, 630 (1983).
I. S. Markovich, N. A. Filigina, V. M. Dziomko, Yu. S. Ryabokobylko, G. M. Adamova, and S. L. Zelichenok, Khim. Geterotsikl. Soedin., No. 2, 185 (1983).
M. G. Voronkov, V. I. Knutov, and M. K. Butin, Khim. Geterotsikl. Soedin., No. 2, 275 (1983).
R. R. Whitney and D. A. Jaeger, Org. Mass Spectrom.,15, 343 (1980).
R. A. Hancock, R. Walder, H. Weigel, V. Gold, and C. M. Sghibartz, Org. Mass Spectrom.,18, 402 (1983).
E. V. Ganin, B. V. Rozynov, V. F. Anikin, and G. L. Kamalov, Khim. Geterotsikl. Soedin., No. 8, 1048 (1984).
P. Traldi, U. Vettori, G. Podda, A. Maccioni, and L. Gorda, Org. Mass Spectrom.,18, 69 (1983).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 783–786, June, 1986.
Rights and permissions
About this article
Cite this article
Terent'ev, P.B., Shmorgunov, V.A., Bogatskii, A.V. et al. Mass-spectrometric behavior of benzo-substituted dibenzo-18-crown-6 ethers. Chem Heterocycl Compd 22, 616–619 (1986). https://doi.org/10.1007/BF00575241
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00575241