Abstract
Potassium metal and an electrochemical method are used to prepare anion radicals from benz-2,1,3-oxa-, -thia-, and -selenadiazoles, and also from naphtho-1,2-furazane and naphtho-1,2-selenadiazoles. The EPR spectra of these anions are analyzed, and the results compared with the calculated distributions of spin densities in the anions. It is concluded that the key heteroatoms in the molecules of the compounds investigated participate in conjugation in a definite way. This conclusion is also based on analysis of the electronic absorption spectra of arene-2,1, 3-X-diazoles. Apparently the distribution of spin density in the heterocyclic ring does not change substantially from benzologs to naphthologs.
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A. Mangini and R. Passerini, Experientia, 12, 49, 1955; G. Modena, Advances of Mol. Spectrosc., Pergamon Press, 483, 1962.
H. H. Jaffe, J. Chem. Phys., 22, 1430, 1954.
R. Y. Friedel and M. Orchin, Ultraviolet Spec-tra of Aromatic Compounds, N. Y., 1951.
H. P. Koch, J. Chem. Soc., 387, 1949.
V. Luzzati, Acta Cryst., 4, 193, 1951.
B. E. Zaitsev, Z. V. Todres, and V. A. Pozdyshev, KhGS [Chemistry of Heterocyclic Com-pounds], 825, 1965.
E. I. Fedin, Z. V. Todres, and L. S. Efros, KhGS [Chemistry of Heterocyclic Compounds], 297, 1967.
V. A. Pozdyshev, Z. V. Todres, and L. S. Efros, ZhOKh, 30, 2551, 1960.
L. S. Efros and Z. V. Todres, ZhOKh, 27, 983, 3127, 1957.
G. Englert and H. Prinzbach, Z. Natur-forsch., 17b, 4–6, 1962.
E. S. Levin, Z. I. Fodiman, and Z. V.Todres, Materials of the Second Conference on Po-larography [in Russian], Kazan, 83, 1962.
E. S. Levin, Z. I. Fodman, and Z. V. Todres, Elektrokhimiya, 2, 175, 1966.
R. H. Rieger, J. Bernal, W. H. Reinmuth, and G. K. Fraenkel, J. Am. Chem. Soc., 85, 683, 1963.
E. T. Strom and G. A. Russell, J. Am. Chem. Soc., 87, 3326, 1965.
M. Karplus and G. K. Fraenkel, J. Chem. Phys., 35, 1312, 1961.
A. Carrington and J. D. Santos-Viega, Mol. Phys., 5, 509. 1962.
E. W. Stone and A. H. Maki, J. Chem. Phys., 39, 1635, 1963.
N. M. Atherton, F. G. Gerson, and J. N. Murrell, Mol. Phys., 6, 265, 1963.
B. L. Barton and G. K. Fraenkel, J. Chem. Phys., 41, 1455, 1965.
A. D. McLachlan, Mol. Phys., 3, 231, 1960.
L. E. Orgell, T. L. Cottrell, W. Dick, and L. E. Sutton, Trans. Faraday Soc., 47, 113, 1951.
E. Streitwieser, Molecular Orbital Theory for Organic Chemists [Russian Translation], Mir, Ch. 5, 1965.
T. R. Tuttl, R. L. Ward, and S. J. Weissman, J. Chem. Phys., 25, 189, 1956.
R. H. Hoskins, J. Chem. Phys., 23, 1975, 1955.
Z. V. Todres, in book: Sulfonation with Salts of Sulfuric Acid [in Russian], Khimiya, 64, 1965.
J. N. Murell, The Theory of the Electronic Spectra of Organic Molecules, London, 171, 1963.
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Solodovnikov, S.P., Todres, Z.V. The problem of conjugation through key heteroatoms in arene-2,1,3-X-diazoles (X=O, S, Se). Chem Heterocycl Compd 3, 641–646 (1967). https://doi.org/10.1007/BF00468333
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DOI: https://doi.org/10.1007/BF00468333