Conclusions
-
1.
The INDO approximation of the SCF MO LCAO method has been used to carry out calculations on the lower triplet state of aromatic molecules with type I substiuents (fluorobenzene, phenol, and aniline), five-membered heteroaromatic compounds (furan and pyrrole), and their cation and anionσ complexes.
-
2.
The experimental data on the photochemical aromatic electrophilic and nucleophilic substitution reactions have been analyzed. It is pointed out that it is possible that these reactions proceed through a triplet σ complex.
Similar content being viewed by others
Literature cited
E. Havinga, R. O. DeJongh, and M. E. Kronenberg, Helv. Chim. Acta,50, 2550 (1967).
J. Cornelisse, Pure Appl. Chem.,41, 433 (1975).
G. Lodder and E. Havinga, Tetrahedron,28, 5563 (1972).
W. J. Spillane, Tetrahedron,31, 495 (1975).
D. A. de Bie and E. Havinga, Tetrahedron,21, 2359 (1965); G. P. de Gunst and E. Havinga, ibid.,29, 2167 (1973); J. G. Lammers and J. Lugtenburg, Tetrahedron Lett., 1777 (1973); C. M. Lok and E. Havinga, Proc. Kon. Ned. Akad. Wetensch.,B77, 1, 15 (1974); R. Zh. Khim., No. 15, Zh 91 (1974).
B. M. Uzhinov, M. G. Kuz'min, Yu. V. Morozov, and I. V. Berezin, Vesta. Mosk. Un-ta. Ser. Khim., No. 5, 62 (1964).
M. G. Kuz'min, Yu. A. Mikheev, and L. N. Guseva, Dokl. Akad. Nauk SSSR,173, 1129 (1967); 176, 368 (1967).
M. G. Kuz'min, B. M. Uzhinov, and I. V. Berezin, Zh. Fiz. Khim.,41, 446 (1967).
W. G. Dauben, L. Salem, and N. J. Turro, Accounts Chem. Res.,8, 41 (1975).
G. R. Howe, J. Chem. Soc. B, 984 (1971).
J. A. Pople, D. L. Beveridge, and P. A. Dobosh, J. Chem. Phys.,47, 2026 (1967).
I. A. Abronin, G. M. Zhidomirov, and Ya. L. Gol'dfarb, Dokl. Akad. Nauk SSSR,218, 363 (1974).
M. B. Groen and H. Havinga, Molec. Photochem.,6, 9 (1974).
S. Mc Glynn, T. Adzumi, and M. Kinoshita, Molecular Spectroscopy of the Triplet State [Russian translation], Mir (1972).
K. Schwetlick and K. Unverferth, J. Prakt. Chem.,314, 603 (1972).
Handbook of Chemistry [in Russian], Vol. 2, 2nd Ed., Khimiya, Leningrad (1964), p. 960.
J. Marino, Khim. Geterotsikl. Soedin., 579 (1973).
Author information
Authors and Affiliations
Additional information
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 3, pp. 588–594, March, 1977.
Rights and permissions
About this article
Cite this article
Abronin, I.A., Belen'kli, L.I. & Zhidomirov, G.M. Reactivities of certain aromatic and heteroaromatic compounds in the lower excited triplet state. Russ Chem Bull 26, 528–532 (1977). https://doi.org/10.1007/BF01179460
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF01179460