Skip to main content
Log in

Radiochemical study of gas-phase reactions of diethylstannyl cations Et2SnT+ with oxygen-containing compounds: II. Reaction of diethylstannyl cations with butanol

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

Gas-phase reaction of nucleogenic diethylstannyl cations Et2SnT+ with butan-1-ol has been studied by the radiochemcal method, and probable reaction mechanisms have been proposed. During the process diethylstannyl cations undergo isomerization into tertiary Me2EtSn+ cations and rearrangement with elimination of ethane. Thermochemical parameters of reactions of diethyl-substituted cations derived from Group 14 elements (Et2TM+; M = C, Si, Ge, Sn) with alcohols have been analyzed by the M06L aug-cc-pVDZ quantum chemical method.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Alferova, A.A., Kochina, T.A., Avrorin, V.V., Sinotova, E.N., and Ignatyev, I.S., Russ. J. Gen. Chem., 2013, vol. 83, no. 5, p. 938. DOI: 10.1134/S1070363213050095.

    Article  CAS  Google Scholar 

  2. Zharov, V.T., Nefedov, V.D., Sinotova, E.N., Korsakov, M.V., and Antonova, V.V., Zh. Org. Khim., 1980, vol. 16, no. 1, p. 35.

    Google Scholar 

  3. Kochina, T.A., Vrazhnov, D.V., and Ignatyev, I.S., J. Organomet. Chem., 2002, vol. 656, nos. 1–2, p. 258. DOI: 10.1016/S0022-328X(02)01625-X.

    Article  CAS  Google Scholar 

  4. Kochina, T.A., Nefedov, V.D., Sinotova, E.N., and Shchukin, E.V., Russ. J. Gen. Chem., 2000, vol. 70, no. 6, p. 885.

    CAS  Google Scholar 

  5. Kochina, T.A., Vrazhnov, D.V., Ignatyev, I.S., and Sinotova, E.N., Russ. J. Gen. Chem., 2003, vol. 73, no. 1, p. 61. DOI: 10.1023/A:1023474402262.

    Article  CAS  Google Scholar 

  6. Alferova, A.A., Kochina, T.A., Avrorin, V.V., and Sinotova, E.N., Russ. J. Gen. Chem., 2011, vol. 81, no. 7, p. 1507. DOI: 10.1134/S1070363211070164.

    Article  CAS  Google Scholar 

  7. Perst, H., Oxonium Ions in Organic Chemistry, Weinheim: Chemie, 1971.

    Google Scholar 

  8. Zhao, Y. and Truhlar, D.G., J. Chem. Phys., 2006, vol. 125, no. 19, no. 194 101. DOI: 10.1063/1.2370993.

    Google Scholar 

  9. Woon, D.E. and Dunning, T.H., J. Chem. Phys., 1993, vol. 98, no. 2, p. 1358. DOI: 10.1063/1.464303.

    Article  CAS  Google Scholar 

  10. Ignatyev, I.S., Montejo, M., and López González, J.J., J. Mol. Model., 2013, vol. 19, p. 5439. DOI: 10.1007/s00894-013-2038-y.

    Article  CAS  Google Scholar 

  11. Egorochkin, A.N. and Voronkov, M.G., Elektronnoe stroenie organicheskikh soedinenii kremniya, germaniya i olova (Electronic Structure of Organic Silicon, Germanium, and Tin Compounds), Novosibirsk, Sib. Otd. Ross. Akad. Nauk, 2000.

    Google Scholar 

  12. Schager, F., Goddard, R., Seevogel, K., and Pörschke, K.-R., Organometallics, 1998, vol. 17, p. 1546. DOI: 10.1021/om970997n.

    Article  CAS  Google Scholar 

  13. Clark, H. and Willis, G.J., J. Am. Chem. Soc., 1960, vol. 82, p. 1888. DOI: 10.1021/ja01493a014.

    Article  CAS  Google Scholar 

  14. Edgell, W.F. and Ward, C.H., J. Am. Chem. Soc., 1955, vol. 77, p. 6486. DOI: 10.1021/ja01629a014.

    Article  CAS  Google Scholar 

  15. The Chemistry of Organic Germanium, Tin and Lead Compounds, Rappoport, Z., Ed., Chichester: Wiley, 2002, vol. 2, p. 1.

  16. Vrazhnov, D.V., Kochina, T.A., Alferova, A.A., and Ignatyev, I.S., Russ. J. Gen. Chem., 2011, vol. 81, no. 6, p. 937. DOI: 10.1134/S1070363211060090.

    Article  Google Scholar 

  17. Speranza, M., Chem. Rev., 1993, vol. 93, no. 8, p. 2933. DOI: 10.1021/cr00024a010.

    Article  CAS  Google Scholar 

  18. Kochina, T.A., Vrazhnov, D.V., Sinotova, E.N., and Voronkov, M.G., Russ. Chem. Rev., 2006, vol. 75, no. 2, p. 95. DOI: 10.1070/RC2006v075n02ABEH002480.

    Article  CAS  Google Scholar 

  19. Voronkov, M.G., Mileshkevich, V.P., and Yuzhelevskii, Yu.A., Siloksanovaya svyaz’ (The Siloxane Bond). Novosibirsk: Nauka, 1976.

    Google Scholar 

  20. Kochina, T.A., Vrazhnov, D.V., Ignatyev, I.S., Sinotova, E.N., and Voronkov, M.G., J. Organomet. Chem., 2011, vol. 696, p. 1331. DOI: 10.1016/j.jorganchem.2011.01.010.

    Article  CAS  Google Scholar 

  21. Myalochkin, D.L., Kochina, T.A., Vrazhnov, D.V., Avrorin, V.V., Sinotova, E.N., and Ignatyev, I.S., Russ. J. Gen. Chem., 2010, vol. 80, no. 11, p. 2283. DOI: 10.1134/S1070363210110095.

    Article  CAS  Google Scholar 

  22. Groenewold, G.S., Gross, M.L., Bursey, M.M., and Jones, P.R., J. Organomet. Chem., 1982, vol. 235, p. 165. DOI: 10.1016/S0022-328X(00)96206-5.

    Article  CAS  Google Scholar 

  23. Boganov, S.E., Faustov, V.I., Egorov, M.P., and Nefedov, O.M., Russ. Chem. Bull., 2004, vol. 53, no. 5, p. 960. DOI: 10.1023/B:RUCB.0000041298.37114.c6.

    Article  CAS  Google Scholar 

  24. Alferova, A.A., Kochina, T.A., Avrorin, V.V., and Sinotova, E.N., Russ. J. Gen. Chem., 2012, vol. 82, no. 11, p. 1925. DOI: 10.1134/S1070363212110308.

    Article  Google Scholar 

  25. Amberger, E. and Kula, M.R., Chem. Ber., 1963, vol. 96, p. 2562. DOI: 10.1002/cber.19630961007.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to T. A. Kochina.

Additional information

Original Russian Text © A.A. Alferova, T.A. Kochina, V.V. Avrorin, E.N. Sinotova, I.S. Ignat’ev, 2014, published in Zhurnal Obshchei Khimii, 2014, Vol. 84, No. 5, pp. 723–728.

For communication I, see [1].

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Alferova, A.A., Kochina, T.A., Avrorin, V.V. et al. Radiochemical study of gas-phase reactions of diethylstannyl cations Et2SnT+ with oxygen-containing compounds: II. Reaction of diethylstannyl cations with butanol. Russ J Gen Chem 84, 816–821 (2014). https://doi.org/10.1134/S1070363214050041

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363214050041

Keywords

Navigation