Abstract
The electronic absorption spectra of 29 pyrrole analogs of the chalcones have been studied in solutions of strong acids and alkalies, in which the corresponding cations and anions are formed. It has been shown by means of the IR spectra that the protonation of the pyrrole chalcones takes place at the carbonyl group. Considerations are given of the structure of the organic cations and anions studied and of the characteristic features in the change in their coloration as a function of their chemical structure. Satisfactory correlations have been found between the shift of the absorption frequency of the long-wave band which takes place at the transition from a neutral solution (molecules) to an acid solution (cations) or to an alkaline solution (anions) and Hammett's o constants. Three 3-(4-halophenyl)-1-(2-pyrryl)propenones not previously reported in the literature have been synthesized.
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References
S. V. Tsukerman, V. P. Izvekov, and V. F. Lavrushin, KhGS, collection: Nitrogen-containing Heterocycles [in Russian], 1, 9, 1967.
Yu. E. Sklyar, R. P. Evstigneeva, O. D. Saralidze, and N. A. Preobrazhenskii, DAN, 157, 367, 1964.
L. Bellamy, Infrared Spectra of Complex Molecules [Russian translation], IL, Moscow, p. 372, 1963.
B. E. Zaitsev, Yu. D. Koreshkov, M. E. Vol'pin, and Yu. I. Sheinker, DAN, 139, 1107, 1961.
B. I. Sukhorukov, A. I. Finkel'shtein, E. P. Zil'berman, A. E. Kulikova, and V. I. Ganina, ZhFKh, 35, 1600, 1961.
G. Fraenkel and C. Franconi, J. Am. Chem. Soc., 82, 4479, 1960.
T. Birchall and R. J. Gilespie, Can. J. Chem., 41, 2642, 1963.
D. Cook, Can. J. Chem. 42, 2721, 1964.
H. E. Kramer and R. Gompper, Tetrah. Let., 969, 1963; Z. Phys. Chem. 48, 349, 1964.
D. Cook. Can. J. Chem., 43, 749, 1965.
P. J. Hoak and Th. J. Boer, Rec. trav. chim., 83, 186, 1964.
S. V. Tsukerman, V. M. Nikitchenko, and V. F. Lavrushin, ZhOKh, 33, 1255, 2563, 1963.
S. V. Tsukerman, A. I. Artemenko, and V. F. Lavrushin, ZhOKh, 33, 2528; 1963, 34, 488, 1964.
S. V. Tsukerman, I. K. Gintse, and V. F. Lavrushin, ZhOKh, 34, 2317, 1964.
A. Treibs, E. Herrman, E. Meissner, and A. Kuhn, Ann., 602, 153, 1957.
A. Treibs and H. G. Kolm, Ann. 606, 166, 1957.
A. Treibs and G. Fritz, Ann., 611, 162, 1958.
R. J. Abraham, E. Bullock and S. S. Mitra, Can. J. Chem., 37, 1859, 1959.
E. B. Whipple, J. Chiang and R. L. Hinnan, J. Am. Chem. Soc., 85, 26, 1963.
J. Chiang and E. B. Whipple, J. Am. Chem. Soc., 85, 2763, 1963.
A. I. Artemenko, Thesis [in Russian], Khar'kov, 1964.
M. Rapoport, C. K. Hancock, and E. A. Meyers, J. Am. Chem. Soc., 83, 3489, 1961.
S. V. Tsukerman, Yu. N. Surov, V. F. Lavrushin, and Yu. K. Yur'ev, KhGS [Chemistry of Heterocyclic Compounds], 2, 868, 1966.
L. A. Jones and C. K. Hancock, J. Org. Chem., 25, 226, 1960.
L. E. Scoggins and C. K. Hancock, J. Org. Chem., 26, 3490, 1961.
V. F. Lavrushin, S. V. Tsukerman, and A. I. Artemenko, ZhOKh, 32, 2551, 1962.
N. Maxim and J. Copuzeanu, Bull. Soc. chim. France [5], 5, 57, 1938.
P. Pfeiffer, Organische Molekulverbindungen, Stuttgart, 1922.
A. Treibs and A. Dietl, Ann., 619, 80, 1958.
S. V. Tsukerman, V. P. Izvekov and V. F. Lavrushin, KhGS [Chemistry of Heterocyclic Compounds], 1, 527, 1965.
S. V. Tsukerman, V. D. Orlov, V. P. Izvekov, V. F. Lavrushin, and Yu. K. Yur'ev, KhGS [Chemistry of Heterocyclic Compounds], 2, 34, 1966.
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Tsukerman, S.V., Izvekov, V.P. & Lavrushin, V.F. Electronic absorption spectra of the cations and anions formed from pyrrole analogs of the chalcones. Chem Heterocycl Compd 4, 595–599 (1971). https://doi.org/10.1007/BF00481026
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DOI: https://doi.org/10.1007/BF00481026