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Russian Journal of Organic Chemistry

, Volume 50, Issue 3, pp 439–441 | Cite as

Quantum chemical study of α-diazocarbonyl bullvalene derivatives and related heterocyclic compounds

  • S. G. Semenov
  • M. V. Makarova
Article
  • 56 Downloads

Abstract

According to the results of PBE0/cc-pVTZ quantum chemical calculations, the equilibrium mixture of α-diazocarbonyl bullvalene derivatives (C10H8N2O) contains an impurity of the corresponding bullvaleno-[1,2,3]oxadiazoles. The carbonyl group in the major tautomer is conjugated with the three-membered ring. The concentration of other tautomers in the equilibrium mixture of two bullvaleno[1,2,3]selenadiazoles is negligible.

Keywords

Quantum Chemical Calculation Oxadiazoles Quantum Chemical Study Equilibrium Mixture Tautomeric Transforma 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

  1. 1.
    Schröder, G., Oth, J.F.M., and Merenyi, R., Angew. Chem., Int. Ed. Engl., 1965, vol. 4, p. 752.CrossRefGoogle Scholar
  2. 2.
    Semenov, S.G. and Makarova, M.V., Russ. J. Gen. Chem., 2012, vol. 82, p. 1527.CrossRefGoogle Scholar
  3. 3.
    Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Montgomery, J.A., Jr., Vreven, T., Kudin, K.N., Burant, J.C., Millam, J.M., Iyengar, S.S., Tomasi, J., Barone, V., Mennucci, B., Cossi, M., Scalmani, G., Rega, N., Petersson, G.A., Nakatsuji, H., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Klene, M., Li, X., Knox, J.E., Hratchian, H.P., Cross, J.B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Ayala, P.Y., Morokuma, K., Voth, G.A., Salvador, P., Dannenberg, J.J., Zakrzewski, V.G., Dapprich, S., Daniels, A.D., Strain, M.C., Farkas, O., Malick, D.K., Rabuck, A.D., Raghavachari, K., Foresman, J.B., Ortiz, J.V., Cui, Q., Baboul, A.G., Clifford, S., Cioslowski, J., Stefanov, B.B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Martin, R.L., Fox, D.J., Keith, T., Al-Laham, M.A., Peng, C.Y., Nanayakkara, A., Challacombe, M., Gill, P.M.W., Johnson, B., Chen, W., Wong, M.W., Gonzalez, C., and Pople, J.A., Gaussian 03, Revision B.05, Wallingford CT: Gaussian, 2004.Google Scholar
  4. 4.
    Schulz, R. and Schweig, A., Angew. Chem., Int. Ed. Engl., 1979, vol. 18, p. 692; Schulz, R. and Schweig, A., Angew. Chem., Int. Ed. Engl., 1984, vol. 23, p. 509.CrossRefGoogle Scholar
  5. 5.
    Semenov, S.G. and Sigolaev, Yu.F., Zh. Strukt. Khim., 2004, vol. 45, p. 1128.Google Scholar
  6. 6.
    Semenov, S.G. and Makarova, M.V., Russ. J. Gen. Chem., 2011, vol. 81, p. 1555.CrossRefGoogle Scholar
  7. 7.
    Schaller, R.J., Gleiter, R., Hofmann, J., and Rominger, F., Angew. Chem., Int. Ed., 2002, vol. 41, p. 1181.CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2014

Authors and Affiliations

  1. 1.St. Petersburg State UniversitySt. PetersburgRussia

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