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  • Polarography in the study of classical organic functional group reactions: II. Polarographic behaviour of 4-CYANOCINNAMIC ACID (cas 16642-94-7) and its ethyl ester

  • Add time:08/15/2019    Source:sciencedirect.com

    SummaryThe polarographic behaviour of 4-CYANOCINNAMIC ACID (cas 16642-94-7) in 50% ethanolic solution shows a marked dependence on pH. At low pH-values a single 4-electron wave is observed, the height of which decreases with increasing pH; the protonated undissociated acid is reduced to a primary amine. A mixed process is observed between pH 6 and 7, and at higher pH-values two waves appear, the total height of which remains constant. The height of the more positive wave decreases with increasing pH, and corresponds to reduction of the C=C bond in a protonated complex of the anion. The more negative wave also corresponds to reduction of the C=C bond in the anion, but in this case electron transfer in the first step in the reaction. At high pH-values the slope of this wave increased, and indicated apparent reversibility, although the overall reaction was irreversible.The behaviour of the ester is simpler. At low pH-values the ester is reduced, as a protonated complex, to a primary amine. At pH-values above 7, hydrolysis occurs, but the C=C bond is reduced in the unprotonated ester itself. A mixed process was observed between pH 4 and 8.

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