Russian Chemical Bulletin

, Volume 47, Issue 6, pp 1228–1229 | Cite as

Reactivity of molecules with nitrogen-containing functional groups toward H+ and SiMe3 + ions

  • V. I. Kadentsev
  • N. D. Chuvylkin
  • A. A. Stomakhin
  • N. G. Kolotyrkina
  • O. S. Chizhov
Brief Communications

Abstract

The equilibrium constants of trimethylsilyl cation transfer reactions differ from those of proton transfer reactions by many orders of magnitude. The basicity of MeCN (1), MeNO2 (2), and Et2NH (3) in the gas phase decreases in the series3≫1>2, whereas the affinity of the same compounds for trimethylsilyl cation decreases in the series1≫3≈2. Semiempirical quantum-chemical MNDO calculations indicate that the formation of MeCN·SiMe3 + ions is thermodynamically more favorable than that of MeNH2·SiMe3 + ions.

Key words

mass spectrometry chemical ionization trimethylsilyl cation basicity acetonitrile nitromethane diethylamine 

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Copyright information

© Plenum Publishing Corporation 1998

Authors and Affiliations

  • V. I. Kadentsev
    • 1
  • N. D. Chuvylkin
    • 1
  • A. A. Stomakhin
    • 1
  • N. G. Kolotyrkina
    • 1
  • O. S. Chizhov
    • 1
  1. 1.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation

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