Abstract
The IR spectra of a number of azlactones and their structural analogs, viz., azlactams, in solutions in carbon tetrachloride and in chloroform and in the solid phase were obtained. The character of the interaction of the carbonyl group of the heteroring with substituents with different electronic natures has a substantial effect on the frequencies of the stretching vibrations of the carbonyl group and the azomethine and ethylene bonds. The carbonyl frequencies were subjected to correlation analysis, and high conductivity of the electronic effects of substituents in the 2-phenyl-4-arylideneoxazol-5-one series was ascertained.
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J. Eisenbrand, Arch. Pharm., No. 9, 441 (1953).
B. M. Krasovitskii, I. V. Lysova, L. Sh. Afanasiadi, M. B. Stryukov, M. I. Knyazhanskii, and Yu. M. Vinetskaya, Zh. Prikl. Spektrosk., No. 3, 434 (1980).
A. R. Katritzky, Physical Methods in the Chemistry of Heterocyclic Compounds, Academic Press (1963).
H. E. Carter and J. W. Hinman, J. Biol. Chem., 178, 403 (1949).
H. Gramstad, Spectrochim. Acta, 19, 497 (1963).
V. I. Savin, Yu. P. Kitaev, and I. I. Saidashev, Izv. Akad. Nauk SSSR, Ser. Khim., No. 4, 851 (1972).
L. Bellamy, Infrared Spectra of Complex Molecules, Methuen (1958).
V. A. Palm, Fundamentals of the Quantitative Theory of Organic Reactions [in Russian], Khimiya, Leningrad (1967), p. 356.
L. P. Pivovarevich, L. A. Kutulya, Yu. N. Surov, L. M. Satanovskii, and S. V. Tsukerman, Reakts. Sposob. Org. Soedin., 9, 47 (1975).
B. M. Krasovitskii, I. V. Lysova, and L. Sh. Afanasiadi, Khim. Geterotsikl. Soedin., No. 2, 158 (1978).
B. M. Krasovitskii, L. Sh. Afanasiadi, Yu. M. Vinetskaya, and I. V. Lysova, USSR Inventor's Certificate No. 767107; Byull. Izobret., No. 36, 120 (1980).
A. Galat, J. Am. Chem. Soc., 72, 4436 (1950).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 171–174, February, 1984.
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Krasovitskii, B.M., Surov, Y.N., Lysova, I.V. et al. Investigation of azlactones and azlactams by IR spectroscopy. Chem Heterocycl Compd 20, 136–139 (1984). https://doi.org/10.1007/BF00506280
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DOI: https://doi.org/10.1007/BF00506280