Highly efficient CCl bond cleavage and unprecedented CC bond cleavage of environmentally toxic DDT through molecular electrochemical catalysis

- The first example of the complete dechlorination of DDT through molecular electrochemical catalysis.
- Highly efficient CCl bond cleavage is achieved and an unprecedented CC bond cleavage reaction also occurs.
- The electronic structure and properties of the molecular catalyst is characterized by various techniques.
- GC-MS has been used to analyze the degradation products and the reaction mechanism is fully described.

The electrocatalytic properties of a Co(II)octaalkoxyphthalocyanine complex (Co(II)Pc) with eight strongly electron-donating substituents provide the first example of the complete dechlorination of DDT through molecular electrocatalysis, rather than the use of metal electrodes which had been achieved previously. Interaction with a highly nucleophilic [Co(I)Pc]2− species results in rapid cleavage of the C(sp3)Cl, C(sp2)Cl and aromatic C(sp2)Cl bonds. Bis(p-chlorophenyl)methanone (BPCl2) is detected in high yield along with its full dechlorination product, diphenylmethanone (BP) and the conventional CCl bond cleavage products, due to an unprecedented CC bond cleavage reaction that is followed by the formation of a C−O bond. Theoretical calculations are used to analyze trends in the electronic structure of the Co(II)octaalkoxyphthalocyanine complex that account for the efficiency of the CCl bond cleavage reactions, and the reaction process and mechanism are analyzed in depth.

105