Abstract
N-Methyl-substituted 1H-imidazo[2,1-a]isoindole, 5H-isoindolo[2,1-a]benzimidazole, and 3H-pyrazolo[5,1-a]isoindole were calculated by the PPP and CNDO/2 methods. On the basis of the canonical and localized MO it was concluded that the examined compounds can, to a first approximation, be regarded as 1,2-disubstituted iso-indoles, i.e., 10π-electron systems. The calculated data are in good agreement with the experimental UV spectra and the chemical properties of the investigated compounds.
Similar content being viewed by others
Literature Cited
F. S. Babichev and V. A. Kovtunenko, The Chemistry of Isoindole [in Russian], Naukova Dumka, Kiev (1983).
B. é. Aren and G. Ya. Vanag, Izv. Akad. Nauk Latv. SSR, Ser. Khim., No. 2, 207 (1968).
R. G. Glushkov and O. Yu. Magidson, Khim. Geterotsikl. Soedin., No. 1, 85 (1965).
F. S. Babichev and L. G. Khil'ko, Ukr. Khim. Zh., 40, 946 (1974).
V. I. Baranovskii, V. F. Brattsev, and A. I. Panin, Methods for the Calculation of the Electron Structures of Atoms and Molecules [in Russian], Izd. Leningradsk. Gosudarstv. Univ., Leningrad (1976).
V. A. Kovtunenko, Z. V. Voitenko, V. L. Sheptun, L. I. Savranskii, A. K. Tyltin, and F. S. Babichev, Ukr. Khim. Zh., 51, 976 (1985).
A. F. Pozharskii, Khim. Geterotsikl. Soedin., No. 6, 733 (1977).
A. I. Konovalov, in: Structures and Reactivities of Organic Compounds [in Russian], Nauka, Moscow (1978), p. 259.
R. T. Kohl, T. Katto, J. N. Brahan, and I. K. Steille, Macromolecules, 11, 340 (1978).
Yu. A. Kruglyak, G. G. Dyadyusha, V. A. Kuprievich, L. M. Podol'skaya, and G. I. Kogan, Methods for the Calculation of the Electron Structures and Electronic Spectra of Molecules [in Russian], Naukova Dumka, Kiev (1969).
D. A. Zhogolev and V. V. Volkov, Methods, Algorithms, and Programs for Quantum-Chemical Calculations of Molecules [in Russian], Naukova Dumka, Kiev (1976).
J. A. Pople and G. A. Segal, J. Chem. Phys., 44, 3289 (1966).
A. I. Kitaigorodskii, P. M. Zorkii, and V. K. Bel'skii, Structures of Organic Substances. Data from Structural Studies [in Russian], Nauka, Moscow (1980).
A. Gordon and R. Ford, The Chemist's Guide [Russian translation], Mir, Moscow (1976).
V. A. Kovtunenko, Z. V. Voitenko, V. L. Sheptun, A. K. Tyltin, A. I. Chernega, Yu. T. Struchkov, and F. S. Babichev, Khim. Geterotsikl. Soedin., No. 11, 1497 (1984).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 646–652, May, 1987.
Rights and permissions
About this article
Cite this article
Kovtunenko, V.A., Voitenko, Z.V., Sheptun, V.L. et al. Electron structures of azoloisoindoles with a nodal nitrogen atom. 1. Derivatives of isoindolobenzimidazole and imidazo- and pyrazoloisoindoles. Chem Heterocycl Compd 23, 535–540 (1987). https://doi.org/10.1007/BF00476382
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF00476382