Abstract
The reactivity indexes of the neutral, dipolar, cationic, and anionic forms of 3-hydroxy-quinoline were calculated by the simple MO LCAO method using dynamic and statistical approximations. The predicted (on the basis of the localization energies) charge distributions, boundary densities, free valence indexes, and orientations of electrophilic substituents for the cationic and anionic forms of 3-hydroxyquinoline are in good agreement with the experimental data. The orientations of nucleophilic and radical substituents for the four forms of 3-hydroxyquinoline are predicted. The reactivity indexes of the neutral form of 3-hydroxyquinoline were calculated by means of the Pariser-Parr-Pople method.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
A Bryson, J. Am. Chem. Soc., 82, 4871 (1960).
F. S. Mason, J. Chem. Soc., 5010 (1957); 674 (1958).
Yu. A. Kruglyak, G. G. Dyadyusha, V. A. Kuprievich, L. M. Podol'skaya, and G. I. Kagan, Methods for the Calculation of Electronic Structures and Electronic Spectra [in Russian], Kiev (1969), p. 108.
V. I. Vedeneev, L. V. Gurvich, V. N. Kondrat'ev, V. A. Medvedev, and E. L. Frankevich, Energies Required to Break Chemical Bonds. Ionization Potentials and Electron Affinities [in Russian] Izd. Akad. Nauk SSSR, Moscow (1962), p. 81.
P. Murray-Rust and J. D. Wright, J. Chem. Soc., A, 247 (1968).
G. P. Bean, A. R. Katritzky, and A. Marzee, Bull. Acad. Polon. Sci., Ser. Sci. Chim., 16 (1968).
N. Donaldson, Chemistry and Technology of Compounds of the Naphthalene Series [Russian translation], Moscow (1953), p. 18.
M. J. S. Dewar and T. Morita, J. Am. Chem. Soc., 91, 4796 (1969).
A. Streitwieser, Molecular Orbital Theory for Organic Chemists, Wiley (1961).
L. D. Smirnov, N. A. Andronova, V. P. Lezina, and K. M. Dyumaev, Izv. Akad. Nauk SSSR, Ser. Khim., 2382 (1970).
M. Shimizi, J. Pharm. Soc. Japan, 64, 10a, 47 (1944).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 191–196, February, 1972.
Rights and permissions
About this article
Cite this article
Zaitsev, B.E., Andronova, N.A., Grachev, V.T. et al. Electronic structure and reactivity of 3-hydroxyquinoline. Chem Heterocycl Compd 8, 171–175 (1972). https://doi.org/10.1007/BF00472351
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00472351