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CaCtaltyaslytst2s021081,98,,9x, F41O3R PEER REVIEW 4 o4fo1f312 Figure 2. Cyclic voltammograms of a 5 mL solution, [PP13]TFSI (red line) and [EMIM]TFSI (blue line), −1 Ficgounrteai2n.iCnygc1li0cmvoMlta4m-iomdogbreanmzsonoiftari5lemuLsinsogluAtgiounn,[dPePr1a3n]TitFrSoIg(ernedatlminoes)pahnedre[E.MScIaMn]rTaFteSI0(.5blVueslin.e), containing 10 mM 4-iodobenzonitrile using Ag under a nitrogen atmosphere. Scan rate 0.5 V s−1. Table 1. Electrochemical parameters for the electrochemical reduction of 1. Table 1 summarizes the electrochemical data obtained for the electrochemical reduction of 1 Solvent Number of Glassy Carbon Silver Cathode Electrocatalytic 1 −1 3 using several solveEnltesctraonds cathode mCaattehroiadles. In all the cases a fast, irreveErffsiebclte(,kctawlom-eolec)tron reduction wave was observed, whereas the electron2 transfer seemed to be faster in silver than in Epc (V) ∆Epc (V) Epc (V) ∆Epc (V) glassy carbon, since the peak width value was reduced from ca. 100 mV (slow electron transfer) to DMF 4 2 −1.85 0.09 −1.37 0.06 10.4 ca. 60 mV (fast electron transfer) [37–40]. Solvent Electrons 1 2 2 2 −1.07 0.07 17.5 Number of electrons involved in the first electron transfer determined by comparison with a 9-Fluorerone redox [PP13]TFSI 2 −1.83 0.12 [EMIM]TFSI 2 −1.84 0.08 −1.29 0.06 12.7 Table 1. Electrochemical parameters for the electrochemical reduction of 1. 1 probe. 2 ∆Ep = Epc − Epc/2. 3 Electrocatalytic effect: Epc(GC) − Epc(Ag). 4 DMF contains 0.10 M TBABF4. Catalysts 2018, 8, x FOR PENEuRmREbVeIrEWof Glassy Carbon Cathode Silver Cathode Epc ∆Epc (V) (V)b −1.37 0.06 −1.07 0.07 −1.29 0.06 Electrocatalytic5Eofff1e3ct (kcal mol−1) 3 10.4 17.5 12.7 DMF 4 [PP13]TFSI [EMIM]TFS I Epc (V) −1.85 −1.83 −1.84 ∆Epc (V) 2 0.09 0.12 0.08 1 Number of electrons involved in the first electron transfer determined by comparison with a 9- Fluorerone redox probe. 2 ∆Ep = Epc − Epc/2. 3 Electrocatalytic effect: Epc(GC) − Epc(Ag). 4 DMF contains 0.10 M TBABF4. To fully establish the electrochemical reduction mechanism of 1 in ionic liquids, a controlled potential electrolysis after the first reduction wave (at a potential value of ca. 0.1 V more negative than the Epc) was performed under an inert atmosphere using either carbon graphite or silver cathodes. The analysis of the sample after the electrolysis showed that, in all the cases, benzonitrile, 2, was the only product formed after the passage of 2F (C mol−1) (Figure 3). The electrochemical processes were monitored by cyclic voltammetry. Figure 3. Experimental conditions and the cyclic voltammogram of a 5 mL solution of 1 (10 mM) before Figure 3. Experimental conditions and the cyclic voltammogram of a 5 mL solution of 1 (10 mM) (black line) and after (blue line) controlled potential electrolysis under an inert atmosphere with a before (black line) and after (blue line) controlled potential electrolysis under an−1i.nert atmosphere glassy carbon electrode (top) and silver electrode (bottom). Scan rate: 0.5 V s with a glassy carbon electrode (top) and silver electrode (bottom). Scan rate: 0.5 V s−1. Taking into account the cyclic voltammetry and controlled potential electrolysis experiments, it is possible to conclude that 1 followed the Electron transfer, Chemical reaction, Electron transfer (ECE) mechanism. Hence, in a first electrochemical step (E) the radical anion, 1 −, was generated. A chemical reaction (C) coupled to this first electron transfer led to a benzonitrile radical and an iodide anion through a C–I bond cleavage reaction. Finally, the radical was reduced to an anion at thePDF Image | Electrocatalytic Processes for the Valorization of CO2
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