Anodic oxidation of amines. Part I. Cyclic voltammetry of aliphatic amines at a stationary glassy-carbon electrode

Abstract

The anodic oxidations of seventeen aliphatic amines have been examined by cyclic voltammetry at a glassy-carbon electrode in aqueous alkaline solution. All are irreversibly oxidized. Primary amines show no wave. Secondary amines show one wave. Most tertiary amines show two waves and the peak potentials of their first waves are less positive than those of secondary amines. The peak potentials of the first wave of substituted tertiary amines shift to more positive values with increasing electronegativityof the substituent, and some amines with a stronglyelectronwithdrawing group give one wave or no wave. A linear relationship is obtained between the pK, values and peak potentials of the first waves for tertiary amines. The postulated reaction mechanism for tertiary amines involves loss of two electrons, followed by reaction with water to form a secondary amine and an aldehyde.

Rapid Screening Method for New Psychoactive Substances of Forensic Interest: Electrochemistry and Analytical Determination of Phenethylamines Derivatives (NBOMe) via Cyclic and Differential Pulse Voltammetry

“…In this case it is likely that peak I is a result of the electrochemical oxidation of the secondary amine present in the NBOMe molecule. Moreover the oxidation potentials observed are similar to those previously described in the literature for other similar compounds containing secondary amines [25][26][27] . The oxidation of the secondary amine (peak I) involves a removal of an electron of the amino-nitrogen atom, leading to the formation of a primary amine which will be attached to the electrode and an aldehyde and likely free primary amine once the latter reached saturation on the SPCE surface ( Figure 1).…”

Voltammetric Oxidation of Drugs of Abuse III. Heroin and Metabolites

“…They show the formation of a secondary amine (norheroin) and an aldehyde (Scheme 1) which is in accordance with the data described in the literature for the oxidation of aliphatic tertiary amines [20,21].…”

“…4). The appearance of a second peak being attributed to further oxidation of the secondary amine formed by oxidation of the aliphatic tertiary amine group has been described in the literature for other aliphatic amines [20].…”

Voltammetric Determination of Microparticles of Some Local Anesthetics and Antithusics Immobilized on the Graphite Electrode

“…It may be assumed that the electroactive centers in the investigated molecules are either aniline groups in benzocaine and procaine [6 ± 8], or amide groups in cinchocaine and lidocaine [9], or tertiary aliphatic amines in procaine, cinchocaine, lidocaine and codeine [10,11]. Esters, ethers and alcohols can not be oxidized at potentials lower than 2 V (vs. SCE) [12].…”