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C 2020, 6, 34 13 of 21 Benzoic acid obtention would be explained because at the potential of electrolysis, p-cyanobenzoic acid is also reduced, since its reduction potential is c. a. −1.36 V (vs. SHE). C 2020, 6, x FOR PEER REVIEW 14 of 21 C DMF 18 (28%) 12 (28%) 34 C EMIM TFSI −1.81 −1.81 16 (28%) 10 (28%) 31 Table 5. Results of the electrocarboxylation of 6 and 7 at 2F. Table 5. Results of the electrocarboxylation of 6 and 7 at 2F. EMIM TFSI 16 (28%) 10 (28%) 31 % Yield (Conversion Rate) Electrochemical Conditions Electrochemical Conditions Carboxylated Products Ar-H Entries Entries 1 2 3 4 Reagent Reagent Cathode Cathode Solvent Solvent % Yield (Conversion Rate) Carboxylated Products Ar-RHeagent 1 2 3 4 DMF −1.86 −1.86 −1.86 −1.86 20 (32%) 10 (32%) 32 38 43 36 43 6 7 6 7 C DMF 20 (32%) 10 (32%) 32 C EMIM TFSI EMIM TFSI 15 (26%) 15 (26%) 7 (26%) 35 7 (26%) 35 Eap (V vs. SHE) 9 9 10 8 Reagent 38 43 36 43 Eap (V vs. SHE) 10 8 DMF −1.81 −1.81 18 (28%) 12 (28%) 34 ElectrocatalyticBehaviourofCyano-Compounds6and7underCO Atmposphere 3.3.1. Electrocatalytic Behaviour of Cyano-Compounds 6 and 7 und2er CO2 Atmposphere Figure6showsseveralcyclicvoltammogramsof6and7undernitrogenandCO atmosphere Figure 6 shows several cyclic voltammograms of 6 and 7 under nitrogen and CO22 atmosphere using silver and glassy carbon (GC) as a cathode. The use of DMF as a solvent and GC as a cathode using silver and glassy carbon (GC) as a cathode. The use of DMF as a solvent and GC as a cathode allows to see a second monoelectronic fast reversible wave after first one (Figure 5). This second wave allows to see a second monoelectronic fast reversible wave after first one (Figure 5). This second wave corresponds to the electrochemical reduction of benzonitrile, which is the only product obtained after corresponds to the electrochemical reduction of benzonitrile, which is the only product obtained after the reduction of compounds 6 and 7. It is noticeable that benzonitrile acts as a redox mediator for CO the reduction of compounds 6 and 7. It is noticeable that benzonitrile acts as a redox mediator for CO22 reductionwhenreactionisperformedunderCO atmosphere,sincethereisanincreaseofthepeak reduction when reaction is performed under CO2 2 atmosphere, since there is an increase of the peak cucrurernretnvtavlualeuaenadnda laoslossosforfevrevresirbsibliitlyityofotfhtihsisesceocnodndrerdeudcutciotinonwwavavee(h(hoommooggeenneeoouussininddirireeccttCO2 2 redreudcuticotniocnatcaltyatliyctipcrporcoecsess(sF(iFgiugruer6eas,6c)a),.c)). Figure 6. Cyclic voltammograms in DMF/0.1M under nitrogen atmosphere and 20–60 mM [CO2] Figure 6. Cyclic voltammograms in DMF/0.1M under nitrogen atmosphere and 20–60 mM [CO2] atmosphere using a solution of 10 mM of 6 (a) with GC (b) Ag. A solution of 10 mM of 7 with (c) GC atmosphere using a solution of 10 mM of 6 (a) with GC (b) Ag. A solution of 10 mM of 7 with (c) GC and (d) Ag. Scan rate 0.5 V s−1. and (d) Ag. Scan rate 0.5 V s−1. The use of silver electrode allows to tune the CO2 reduction mechanism. In this case the current The use of silver electrode allows to tune the CO2 reduction mechanism. In this case the current value of the first reduction is increasing as well as the peak potential value is shifting when the value of the first reduction is increasing as well as the peak potential value is shifting when the concentration of CO2 is rising. These results can be explained taking into account that under these experimental conditions two electrochemical processes are happening at the electrode surface at same potential; the reduction of the cyanoaromatic halide and the direct reduction of CO2 (Figures 6b,d). The same trend is observed with the use of copper cathode and a ionic liquid with widePDF Image | Electrochemical Tuning of CO2 Reactivity in Ionic Liquids
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