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• W1569058936 abstract "Abstract The mechanisms of electroreduction of 2-, 3-, and 4-pyridinecarboxaldehydes have been studied in aqueous buffered solutions of pH between 2 and 12 by means of dc and differential pulse polarography, linear-sweep voltammetry and controlled-potential electrolysis. Spectroscopic measurements confirmed that these compounds in aqueous solutions exist in equilibria involving both the hydrated and unhydrated forms. The degree of hydration depends strongly on protonation both of the pyridine ring and of the side-chain. Dehydration reactions producing the aldehyde species occur prior to the electron (and possibly the proton) transfer. The loss of water can take place from a protonated geminal diol form or from a neutral diol, depending on pH. Alternatively, the geminal diol anion can eliminate hydroxide ion. A diprotonated pyridinecarboxaldehyde is the electroactive species at pH 8 manifested by an increase of the total limiting current. In this reaction the rate-determining step is the dissociation of a proton from the geminal diol forming a geminal diol anion, which is followed by a rapid elimination of a hydroxide ion to yield the reducible aldehyde. Reaction schemes involving sequences of hydration-dehydration and acid-base reactions as well as electron transfers at mercury electrodes have been proposed for the three isomers. The predominating processes in individual pH-ranges have been pointed out. Electroreduction of the 3-aldehyde occurs up to pH 10 in a single two-electron step. The 2- and 4-aldehydes are reduced between pH 2 and 12 in two, one-electron steps. Electrodimerization occurs at the potential of the limiting current of the first one-electron wave for the 2- and 4-isomer, similarly as for the 3-isomer at pH > 10, where its reduction occurs in a single one-electron wave. Surface dimerization or reaction of the electrolysis products with the parent aldehyde was considered in interpretation of the reduction of the 4-pyridinecarboxaldehyde at pH > 7. Electropolymerization accompanies the reduction of 2-pyridinecarboxaldehyde in alkaline media." @default.
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• W1569058936 date "1986-11-01" @default.
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• W1569058936 title "Polarographic reduction of aldehydes and ketones" @default.
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• W1569058936 doi "https://doi.org/10.1016/0022-0728(86)80207-8" @default.
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