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 language | English (US) |
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Pages (from-to) | 777-788 |
Number of pages | 12 |
Journal | Canadian Journal of Chemistry |
Volume | 81 |
Issue number | 6 |
DOIs | |
State | Published - Jun 1 2003 |
Keywords
- Fragmentation
- Radical cation
- Silane
- Steric effects
- Two-electron sensitization
ASJC Scopus subject areas
- Catalysis
- Chemistry(all)
- Organic Chemistry