Abstract
The electronic structures of benzo[c][1,2,5]oxadiazole, benzo[c][1,2,5]thiadiazole, benzo[c][1,2,5]selenadiazole, naphtho[1,2-c][1,2,5]oxadiazole, naphtho[1,2-c][1,2,5]thiadizole, naphtho[1,2-c][1,2,5]selenadiazole, naphtho[2,3-c][1,2,5]oxadiazole, naphtho-[2,3-c][1,2,5]thiadiazole, and naphtho[2,3-c][1,2,5]selenadiazole have been investigated in the π-electronic approximation by the Pariser-Parr-Pople method. Molecular diagrams have been calculated and the energies of the first singlet transitions have been calculated. A correspondence has been found between the calculated results and those obtained by experiment (UV spectra, reactivities, etc.).
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Z. V. Todres, F. M Stoyanovich, Ya. L. Gol'dfarb, and D. N. Kursanov, Khim. Geterotsikl. Soedin., 632 (1973).
J. Pople, Trans. Faraday Soc., 49, 1375 (1953).
E. Strom and G. Russell, J. Am. Chem. Soc., 87, 3326 (1965).
V. V. Plemenkov and E. G. Kataev, in: The Structure of Molecules and Quantum Chemistry [in Russian], Izd-vo Naukova Dumka, Kiev (1970), p. 142.
M. Kamiya, Bull. Chem. Soc. Japan, 43, 3344 (1970).
N. Brown, D. Tuler, and J. Double, Spectrochim. Acta, A26, 2133 (1970).
B. Hinze and H. Jaffe, J. Phys. Chem., 67, 1501 (1963).
C. Moore, Atomic Energy Levels, Nat. Bur. Stand., Washington, Circular, 467 (1949).
N. Mataga and K. Nishimoto, J. Phys. Chem., 13. 140 (1953).
R. Pariser and R. Parr, J. Chem. Phys., 21, 767 (1953).
D. Sappenfield and M. Kreevoy, Tetrahedron, 19, 157 (1962).
T. Peacock, Proc. Roy. Soc., 78, 460 (1961).
R. Mulliken, C. Rieke, D. Orloff, and H. Orloff, J. Chem. Phys., 17, 1248 (1949).
V. Luzzati, Acta Cryst., 4, 193 (1951).
D. Cruickshank and R. Sparks, Proc. Roy. Soc., 1258 (1960).
Yu. A. Kruglyak, G. G. Dyadyusha, V. A. Kuprievich, L. M. Podol'skaya, and G. I. Kagan, Methods of Calculating the Electronic Structures and Spectra of Molecules [in Russian], Naukova Dumka, Kiev (1969).
L. S. Éfros and Z. V. Todres, Zh. Obshch. Khim., 27, 3121 (1957).
B. E. Zaitsev, Z. V. Todres, and V. A. Pozdyshev, Khim. Geterotsikl. Soedin., 825 (1965).
T. Hollas and R. Wright, Spectrochim. Acta, 25A, 1211 (1969).
M. Cava and R. Schlessinger, Tetrah. Lett., 3815 (1964).
W. Weinstock, P. Davis, D. Mulvey, and J. Schalffer, Angew. Chem., 79, 315 (1967).
R. Phan-Tan-Luu, Bull. Soc. Chim. France, 3283 (1967).
E. Salgebarth and A. Cox, J. Chem. Phys., 43, 170 (1965).
F. Momany and R. Boham, J. Am. Chem. Soc., 86, 162 (1964).
S. I. Zhdanov, V. Sh. Tsveniashvili, and Z. V. Todres, J. Polarogr. Soc., 13, 100 (1967).
N. Atherton, J. Ockwell, and R. Dietz, J. Chem. Soc., A, 771 (1967).
É. S. Levin, Z. M. Fodiman, and Z. V. Todres, Élektrokhimiya, 2, 175 (1966).
Z. V. Todres, S. I. Zhdanov, and V. Sh. Tsveniashvili, Izv. Akad. Nauk SSSR, Ser. Khim., 975 (1969).
K. Fukui, in: Modern Quantum Chemistry [Russian translation], Mir (1968), p. 59.
S. V. Bogdanov and B. I. Karavaev, Zh. Obshch. Khim., 21, 1915 (1951).
S. V. Bogdanov and S. F. Petrov, Zh. Obshch. Khim., 24, 385 (1954).
V. G. Pesin and L. A. Kaukhova, Zh. Vses. Khim. Obshchestva im. D. I. Mendeleeva, 17, 225, 348 (1972).
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For Communication XVIII, see [1].
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1473–1478, November, 1973.
In conclusion, we express our gratitude to D. A. Bochvar and A. A. Bagatur'yants for a discussion of the results obtained.
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Gyul'maliev, A.M., Stankevich, I.V. & Todres, Z.V. An investigation in the field of aromatic heterocycles. Chem Heterocycl Compd 9, 1331–1336 (1973). https://doi.org/10.1007/BF00470335
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DOI: https://doi.org/10.1007/BF00470335