Substitution of the halogen atoms in α-halogenonitro compounds of the aliphatic series. 5. Use of the MNDO method to explain the behavior of the chlorine atom in the substitution reactions of chloronitroacetic acid derivatives

  • A. I. Yurtanov
  • V. I. Shestov
  • I. V. Martynov
Physical Chemistry
  • 21 Downloads

Abstract

The geometric parameters, bond orders, and charge distributions in the molecules of ethyl nitroacetate (I), ethyl chloronitroacetate (II), chloronitroacetamide (III), ethyl chloroacetate (IV), and the anions of ethyl chloronitroacetate (V) and chloronitroacetamide (VI) were calculated by the MNDO method. On the basis of the calculated data and their comparison with the data from x-ray crystallographic analysis (XCA) it was concluded that the nitro group in (II) and (III) is substituted relatively easily, that the order of the C-N bond in (V) and (VI) is close to first, that the charges in the anions alternate, and that there is no conjugation in the C-Cl bond in the
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Keywords

Ethyl Chlorine Geometric Parameter Acid Derivative Halogen 

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Literature cited

  1. 1.
    S. S. Novikov, G. A. Shvekhgeimer, V. V. Sevost'yanova, and V. A. Shlyapochnikov, Chemistry of Aliphatic and Alicyclic Nitro Compounds [in Russian], Khimiya, Moscow (1974), pp. 121, 357, 358, 367.Google Scholar
  2. 2.
    A. I. Yurtanov, A. V. Yarkov, T. I. Ignat'eva, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 11, 2549 (1988).Google Scholar
  3. 3.
    A. I. Yurtanov and I. V. Martynov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 12, 2729 (1989).Google Scholar
  4. 4.
    I. V. Martynov and Yu. L. Kruglyak, Zh. Obshch. Khim.,37, No. 5, 1132 (1967).Google Scholar
  5. 5.
    I. V. Martynov, Yu. L. Kruglyak, and N. F. Privezentseva, Chemistry and Application of Organophosphorus Compounds [in Russian], Nauka, Moscow (1972), p. 273.Google Scholar
  6. 6.
    I. V. Martynov, L. V. Postnova, R. Kh. Bikkeneev, and A. I. Yurtanov, Zh. Obshch. Khim.,20, No. 8, 1724 (1984).Google Scholar
  7. 7.
    V. I. Shestov, I. V. Martynov, A. I. Yurtanov, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 9, 1998 (1987).Google Scholar
  8. 8.
    M. J. S. Dewar and W. Thiel, J. Am. Chem. Soc.,99, 4899 (1977).Google Scholar
  9. 9.
    D. R. Armstrong, R. G. Perkins, and J. J. P. Stewart, J. Chem. Soc., Dalton Trans., No. 8, 838 (1973).Google Scholar
  10. 10.
    A. N. Chekhlov, A. I. Yurtanov, and I. V. Martynov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 6, 1300 (1987).Google Scholar
  11. 11.
    A. N. Chekhlov, A. I. Yurtanov, and I. V. Martynov, Dokl. Akad. Nauk SSSR,282, 323 (1985).Google Scholar
  12. 12.
    A. N. Chekhlov, A. I. Yurtanov, and I. V. Martynov, Kristallografiya,31, No. 2, 270 (1986).Google Scholar
  13. 13.
    R. Gordon and R. Ford, The Chemist's Companion, Wiley-Interscience (1973).Google Scholar
  14. 14.
    O. A. Reutov, I. P. Beletskaya, and K. P. Butin, CH Acids [in Russian], Nauka, Moscow (1980), p. 83.Google Scholar
  15. 15.
    A. N. Vereshchagin, The Inductive Effect. Substituent Constants for Correlation Analysis [in Russian], Nauka, Moscow (1985), p. 5.Google Scholar
  16. 16.
    A. L. Fridman, V. D. Surkov, and S. S. Novikov, Usp. Khim.,49, No. 11, 2159 (1980).Google Scholar

Copyright information

© Plenum Publishing Corporation 1991

Authors and Affiliations

  • A. I. Yurtanov
    • 1
  • V. I. Shestov
    • 1
  • I. V. Martynov
    • 1
  1. 1.Institute of Physiologically Active SubstancesAcademy of Sciences of the USSRChernogolovka

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