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Synthesis on the basis of electrogenerated carbenes

10. Correlation of the energetics of α-elimination and nucleophilic substitution based on the results of quantum chemical calculations

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Abstract

On the base of the semi-empirical MNDO, AM1, and PM3 methods of calculation, the reactivities of halomethane anions in α-eliminations andS N2 reactions with participation of the initial polyhalomethanes have been compared and the dependence of the reactivity on the number of halogen atoms and solvent polarity has been investigated. The possibility of proton transfer when the initial polyhalomethane is C-H-acid has been also discussed.

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References

  1. I. A. Machkarovskaya, K. Ya. Burshtein, and V. A. Petrosyan,Izv. Akad. Nauk, Ser. Khim., 1995 [Russ. Chem. Bull., 1995,44, 2053 (Engl. Transl.)].

  2. I. A. Machkarovskaya, K. Ya. Burshtein, and V. A. Petrosyan,Izv. Akad. Nauk, Ser. Khim., 1989, 1304 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1989,38, 1188 (Engl. Transl.)].

    Google Scholar 

  3. I. A. Machkarovskaya, K. Ya. Burshtein, and V. A. Petrosyan,Izv. Akad. Nauk. Ser. Khim., 1989, 1309 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1989,38, 1193 (Engl. Transl.)].

    Google Scholar 

  4. M. J. S. Dewar and W. Thiel,J. Am. Chem. Soc., 1975,97, 1285.

    Google Scholar 

  5. A. V. Bukhtiarov, V. N. Golishin, A. P. Tomilov, and O. V. Kuz'min,Dokl. Akad. Nauk SSSR, 1987,294, 875.

    Google Scholar 

  6. M. E. Niyazimbetov, T. Yu. Rudashevskaya, L. V. Adaevskaya, and V. A. Petrosyan,Izv. Akad. Nauk, Ser. Khim., 1990, 1802 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1990,39, 1633 (Engl. Transl.)].

    Google Scholar 

  7. M. J. S. Dewar, E. G. Zoebisch, and E. F. Healy,J. Am. Chem. Soc., 1985,107, 3902.

    Google Scholar 

  8. J. J. P. Stewart,J. Comp. Chem., 1989,2, 221.

    Google Scholar 

  9. K. Ya. Burshtein,Zh. Strukt. Khim., 1987,28, 3 [J. Struct. Chem., 1987,28 (Engl. Transl.)].

    Google Scholar 

  10. R. D. Levin and S. G. Lias,J. Phys. Chem Ref. Data, 1988,17, Suppl. 1.

  11. A. A. Voityuk,Zh. Strukt. Khim., 1988,29, 138 [J. Struct. Chem., 1988,29 (Engl. Transl.)].

    Google Scholar 

  12. E. H. Mottus, M. R. Ort,J. Electrochem. Soc., 1970,117, 885.

    Google Scholar 

  13. G. P. Girina, V. A. Kokorekina, Zh. I. Krinetz, L. G. Feoktistov, and V. A. Petrosyan,Elektrokhimiya, 1990,26, 738.

    Google Scholar 

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., Moscow, Russian Federation

    I. A. Machkarovskaya & V. A. Petrosyan

  2. Semenov Institute of Chemical Physics, Russian Academy of Sciences, 4 ul. Kosygina, Moscow, Russian Federation

    K. Ya. Burshtein

Authors
  1. I. A. Machkarovskaya
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  2. K. Ya. Burshtein
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  3. V. A. Petrosyan
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Additional information

For 9 see Ref. 1.

Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2155-2158, November, 1995.

This work was partially supported by the International Science Foundation (Grant No. MHYOO).

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Machkarovskaya, I.A., Burshtein, K.Y. & Petrosyan, V.A. Synthesis on the basis of electrogenerated carbenes. Russ Chem Bull 44, 2060–2063 (1995). https://doi.org/10.1007/BF00696704

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