Abstract
On the basis of IR and electronic spectra and quantum-chemical calculations, a conclusion has been drawn regarding the structure of phenanthridone and its derivatives: It has been confirmed that in the crystalline state and in solutions, phenanthridones exist primarily in the lactam form. An interpretation is given for the longwave bands in the electronic absorption spectra. Certain spectral criteria are proposed for determining the positions of substituents in the phenyl rings of phenanthridones, and the direction of aromatic substitution of the lactim and cationic forms of phenanthridone have been evaluated. Acid association constants of phenanthridone and its derivatives have been determined.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
I. A. Migel', E. A. Gastilovich, V. G. Klimenko, and K. A. Mishchenina, Zh. Fiz. Khim., 62, No. 8, 2071 (1988).
Hsi-Lung Pan and T. L. Fletcher, J. Heterocycl. Chem., 7, 313 (1970).
B. E. Zaitsev, N. G. Grekhova, G. V. Sheban, and K. M. Dyumaev, Khim. Geterotsikl. Soedin., No. 10, 1388 (1982).
G. A. Val'kova, R. R. Shifrina, D. N. Shigorin, A. M. Andrievskii, A. N. Poplavskii, and K. M. Dyumaev, Zh. Fiz. Khim., 59, 931 (1985).
D. P. Shigorin, G. A. Val'kova, T. V. Sakhno, and A. M. Andrievskii, Zh. Fiz. Khim., 56, 730 (1982).
G. A. Val'kova, T. V. Sakhno, S. N. Shcherbo, D. N. Shigorin, A. M. Andrievskii, A. N. Poplavskii, and K. M. Dyumaev, Zh. Fiz. Khim., 54, 2416 (1980).
Kumar Sen Deb, J. Cryst. Mol. Struct., 6, 153 (1976).
L. A. Chetkina, Z. P. Povet'eva, and V. K. Bel'skii, Dokl. Akad. Nauk SSSR, 266, 1191 (1982).
G. I. Migachev, N. G. Grekhova, and A. M. Terent'ev, Khim. Geterotsikl. Soedin., No. 3, 388 (1981).
G. I. Migachev and A. M. Terent'ev, Khim. Geterotsikl. Soedin., No. 3, 394 (1981).
M. J. S. Dewar, The Molecular Orbital Theory of Organic Chemistry, McGraw-Hill, New York (1969) [Russian translation, Mir, Moscow (1972), p. 183].
G. I. Kagan, V. A. Kosobutskii, V. K. Belyakov, and O. G. Tarakanov, Khim. Geterotsikl. Soedin., No. 6, 183 (1972).
D. I. Cook. Can. J. Chem., 42, 2294 (1964).
A. Albert and E. P. Serjeant, Ionization Constants of Acids and Bases, Methuen, London (1962) [Russian translation, Khimiya, Moscow-Leningrad (1964), p. 47].
A. R. Katritzky and J. M. Lagowski (editors), Principles of Heterocyclic Chemistry, Academic Press, New York (1968).
Hsi-Lung Pan and T. L. Fletcher, J. Heterocycl. Chem., 7, No. 3, 598 (1970).
A. V. Iogansen, The Hydrogen Bond [in Russian], Nauka, Moscow (1981), p. 112.
L. J. Bellamy, The Infra-Red Spectra of Complex Molecules, 2nd ed., Methuen, London (1954).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1361–1368, October, 1992.
Rights and permissions
About this article
Cite this article
Zaitsev, B.E., Migachev, G.I., Koval'chukova, O.V. et al. Spectral characteristics, structure, and properties of phenanthridone derivatives. Chem Heterocycl Compd 28, 1159–1165 (1992). https://doi.org/10.1007/BF00529580
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00529580