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C 2020, 6, 34 12 of 21 Table 4. Electrochemical parameters for electroreduction of compounds 6 and 7 in DMF/0.1M TBA BF4 and EMIM TFSI. DMF/0.1M TBA BF4 Entries Cyano Derivative WE 1 Ag 2 6 Cu 3 C 4 Ag 5 7 Cu 6C EMIM TFSI 7 Ag 8 6 Cu 9C SchSecmhem7e.E7.CEECpErporpoopsoaslamlmeecchhaanniissmfortheellecttrroocchheemmiciaclarlerdeudcuticotnioonfo6fa6ndan7d. 7. FiguFriegu5rce,sd5cs,dhoswhowthtahtathhaallobenzoniittrriilleessshsohwowedetdhethsaemseaemleectreolechctermocichaelmbeihcavliobre,haafvirisotrt,wao-first two-eelelecctrtoronnreredduuctciotinonwwavaevies isobosbesrevrevdefdorfohrahloableonbzeonnziotrnilietsril(eFsig(uFriegsu5rae,b5)a,ibn) ninitrnoigtreongaendancadrbcoanrbon Epc (V vs. SHE) −1.73 −1.80 −1.81 −1.47 −1.87 −1.73 −1.80 −1.80 −1.78 ∆Ep (mV) 85 78 96 201 140 99 52 65 68 13 of 21 important to remark that when cyano derivatives are used, it is possible to electrogenerate a strong C 2020, 6, x FOR PEER REVIEW 10 Ag −1.61 70 12 C −1.71 72 11 7 Cu −1.85 80 nucleophile (benzonitrile anion), which is stable enough under our experimental conditions for reacting with CO2 leading to the corresponding electrocarboxylated product. dioxide atmosphere. In none of the cases the presence of oxalate anion was detected. dioxide atmosphere. In none of the cases the presence of oxalate anion was detected. Once the electrochemical reduction mechanism of halobenzonitriles under CO2 atmosphere was Once the electrochemical reduction mechanism of halobenzonitriles under CO2 atmosphere disclosed, electrocarboxylation process were performed using carbon graphite rod. For all the was disclosed, electrocarboxylation process were performed using carbon graphite rod. For all the compounds the applied potential was 0.1 V more negative than potential of the first reduction wave. compounds the applied potential was 0.1 V more negative than potential of the first reduction wave. The results of carboxylation reactions were summarized in Table 5. It could observe that p- The results of carboxylation reactions were summarized in Table 5. It could observe that p-cyanobenzoic cyanobenzoic acid (9) and benzoic acid (10) were obtained in moderated yields after the passage of acid (9) and benzoic acid (10) were obtained in moderated yields after the passage of 2F. Benzonitrile (8) 2F. Benzonitrile (8) is also obtained, showing that there was a competition between carboxylation and is also obtained, showing that there was a competition between carboxylation and protonation process. protonation process. 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).PDF Image | Electrochemical Tuning of CO2 Reactivity in Ionic Liquids
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