Croatica Chemica Acta, Vol. 80 No. 1, 2007.
Original scientific paper
The Electrochemical Behaviour of Novel Multifunctional a-Hydroxymethylated Nitroalkenes at Glassy Carbon and Wax Impregnated Carbon Paste Electrodes
Ronald J. Mascarenhas
Irishi N. Namboothiri
Bailure S. Sherigara
Kittappa M. Mahadevan
Abstract
The electrochemical behaviour of novel multifunctional a-hydroxymethylated nitroalkenes was
studied with respect to oxidation of –OH moiety and reduction of nitro group using the cyclic
voltammetric technique at glassy carbon and wax impregnated carbon paste electrodes with
sulphuric acid as the supporting electrolyte. The –OH moiety attached to the nitroalkene side
chain was found to undergo irreversible four electrons electrochemical oxidation to form an
acid at the glassy carbon electrode but no oxidation was observed at the wax impregnated carbon
paste electrode. Oxidation in sulphuric acid medium becomes easier with increasing the
sulphuric acid concentration. This unusual behaviour is attributed to the formation of a sixmembered
cyclic structure at lower concentrations of sulphuric acid due to intramolecular hydrogen
bonding. Going to the lower potential range, reduction of nitro group was observed in
sulphuric acid medium both at the glassy carbon and wax impregnated carbon paste electrodes.
A comparative study indicated easier reduction at the glassy carbon electrode. Non hydroxymethylated
beta nitroalkenes undergo reduction at a lower negative potential compared to the
corresponding a-hydroxymethylated nitroalkenes.
Keywords
a-hydroxymethylated nitroalkenes; wax impregnated carbon paste electrode; electrochemical investigation; electroreduction
Hrčak ID:
12824
URI
Publication date:
11.3.2007.
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