Journal of the American Chemical Society, Vol.130, No.36, 12163-12167, 2008
The benzil-cyanide reaction and its application to the development of a selective cyanide anion indicator
The benzil-cyanide reaction is a cyanide-specific reaction that has been exploited to produce a colorimetric indicator for this toxic anion. This was done by producing a pi-extended analogue of benzil, 7, which is soluble in a 70:30 (v/v) mixture of methanol-water. In this medium, dilute solutions of 7 are yellow but produce colorless products when exposed to low concentrations of cyanide anion (>= 1.7 mu M; added as an aqueous NaCN solution), but no other common anions (e.g., OH-, F-, N-3(-), benzoate(-), and H2PO4-). On the basis of these observations and supporting mechanistic analyses, it is concluded that the modified benzil system 7 is a promising cyanide anion indicator that is attractive in terms of its selectivity, ease-of-use, water compatibility, and the low, naked-eye discernible cyanide detection limit it provides.