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C 2020, 6, 34 5 of 21 under vacuum using activated molecular sieves for 24 h to make sure that the amount of water was always less than H2O ≤ 0.001% [142]. 2.2. Methods 2.2.1. Cyclic Voltammetry All electrochemical experiments were performed in an electrochemical conical cell with a set-up of the three-electrode system. For CV experiments, the working electrode is a vitreous carbon disk (1 mm diameter), silver disk (3 mm diameter) and copper disk (3 mm electrode). The counter electrode is a Pt disk (<1 mm diameter). All electrodes are polished using a 1 mm diamond paste. All the electrochemical potentials were measured using a saturated calomel electrode, SCE (+0.2411 V vs. SHE) isolated from the working electrode compartment by a salt bridge (salt-solution of the reference calomel electrode is separated from the electrochemical solution by a salt-bridge ended with a ceramic material frit, allowing ionic conduction between the two solutions and avoiding appreciable contamination). Ideally, the electrolyte solution present in the bridge is the same as the one used for the electrochemical solution in order to minimize junction potentials. When such a bridge is used, the ions in the bridge are present in large excess at the junction and they carry almost the whole of the current across the boundary. In our case were used DMF/0.1M TBA BF4 (trying to weigh the same amount of support electrolyte that in the electrolyte solution) or EMIM TFSI, in both cases without electroactive substance. The error associated with the potential values is less than 5 mV. The ohmic drop can be one of the main sources of error when ILs are used as solvents, since they are more resistive media than aprotic polar solvents with 0.1 M concentration of supporting electrolyte. Before and after performing any electrochemical experiments, the solution is purged with inert gas (nitrogen or argon) for 20 min to avoid secondary reactions associated to OER and ORR due to dissolved oxygen in the solution [143,144]. The number of electrons involved in the first reduction process of nitro-compounds were determined by comparison with very well-known one-electron reduction of 9-fluorenone (redox probe), in the same medium using the same electrochemical set-up, by terms of cyclic voltammetry. It is used 9-fluorenone and nitrobenzene as probe because both compounds have the same magnitude value of diffusion coefficient without further limitations (DMF (10−9 m2·s−1) nor ionic liquids (10−11 m2·s−1) [145,146]. The number of electrons involved in this first electron transfer was also confirmed by controlled-potential electrolysis. 2.2.2. Electrocarboxylation Processes Cyano-compounds were electrolyzed at a negative potential of ~0.1 V more negative than the Epc potential value under nitrogen/argon or carbon dioxide saturated solutions. When the reaction is completed, the resulting solution in the electrolysis is extracted with ether. The organic layer is dried with Na2SO4 and evaporated to yield a residue that is analyzed by gas chromatography-mass spectrometry, and Proton Nuclear Magnetic Resonance (1H-NMR). Thus, all products obtained, and the commercial analogues were characterized by 1H-NMR. Measurements were made using a DPX360 (250 MHz) spectrometer (Bruker, Billerica, MA, USA) spectrometer. Proton chemical shifts were reported in ppm (d) (CDCl3, δ 7.26, or CD3CN, δ 1.94). The J values are reported in Hz. Benzonitrile (8). Colorless liquid, 31–35% yield. 1H-NMR (CDCl3) δ (ppm): 7.70–7.55 (m, 3H), 7.47 (t, J = 7.4 Hz, 2H). 4-Cyanobenzoic acid (9). Yellow pale solid, 15–20% yield. 1H-NMR (CDCl3) δ (ppm): 8.19 (d, J = 8.5 Hz, 2H), 7.78 (d, J = 7.6 Hz, 2H). Benzoic acid (10). Colorless solid, 7–12% yield. 1H-NMR (CDCl3) δ (ppm): 8.13 (d, J = 7.5 Hz, 2H), 7.62 (t, J = 6.8 Hz, 1H), 7.48 (t, J = 6.9 Hz, 2H). When pure IL is used as electrolyte, the products of the electrolyzed solution are extracted with ether, allowing one to recover almost an 80% of the IL at the end of the experiment [147].PDF Image | Electrochemical Tuning of CO2 Reactivity in Ionic Liquids
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