Aminosilanes as two-electron donors: A technological application of radical cation chemistry

Ian Gould, Stephen A. Godleski, Paul A. Zielinski, Samir Farid

Research output: Contribution to journalArticle

16 Scopus citations

Abstract

Aminosilanes possess the appropriate structural features for use as two-electron sensitizers in silver halide photography. Here, we describe studies of the nucleophile-assisted cleavage reactions of the C - Si bonds in their radical cations. Water is identified as a useful nucleophile. It is found that the kinetics of these reactions are best described by taking into account a radical cation - water complex. The cleavage reactions are also controlled by steric effects at silicon and by the proximity of a carboxylate group that can modify the nucleophilicity of the water. Cleavage forms an α-amino radical that can donate a second electron to 9,10-dicyanoanthracene as a solution-phase electron acceptor.

Original languageEnglish (US)
Pages (from-to)777-788
Number of pages12
JournalCanadian Journal of Chemistry
Volume81
Issue number6
DOIs
StatePublished - Jun 1 2003

Keywords

  • Fragmentation
  • Radical cation
  • Silane
  • Steric effects
  • Two-electron sensitization

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Organic Chemistry

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