Synthesis and electrochemical study of nitrophenyl derivatives of β-cyclodextrin

• Published in: Journal of physical organic chemistry 2007-06, Vol.20 (6), p.375-383
• Main Authors: Gubica, Tomasz, Stroka, Jadwiga, Temeriusz, Andrzej
• Format: Article
• Language: English
• Subjects: cyclic voltammetry; inhibition of electrode reactions; mercury electrode; nitrophenyl-β-cyclodextrin
• ISSN: 0894-3230; 1099-1395
• DOI: 10.1002/poc.1149

A series of nitrophenyl β‐cyclodextrin derivatives: mono[6‐deoxy‐6‐(4‐nitrobenzamido)]‐per‐ O‐methyl‐β‐cyclodextrin (R1PhNO2), mono[6‐deoxy‐6‐(3‐nitrobenzamido)]‐per‐O‐methyl‐β‐cyclodextrin (R2PhNO2) and heptakis[6‐deoxy‐6‐(4‐nitrobenzamido)‐2,3‐di‐O‐methyl]‐β‐cyclodextrin [R3(PhNO2)7] were synthesized. Purity and composition of the obtained substances were checked. Electroreduction of nitro groups of the new synthesized compounds was investigated on mercury electrode using cyclic voltammetry and chronocoulometry. The parameters of the reduction processes of NO2 groups of the investigated compounds were found not to be comparable to the reduction of nitrobenzene under the same experimental conditions. Moreover, the electroreduction of nitro groups in these nitrophenyl derivatives was dependent on pH, the type of the studied compound, and slightly on the solvent composition. All the reactants were strongly adsorbed on mercury electrode. In the case of R3(PhNO2)7, its seven nitro groups were reduced practically at the same potential, and no radical anion formation was observed. Copyright © 2007 John Wiley & Sons, Ltd. The parameters of the reduction processes of NO2 groups of the investigated compounds were found not to be comparable to the reduction of nitrobenzene under the same experimental conditions. In the case of R3(PhNO2)7, its seven nitro groups were reduced practically at the same potential, and no radical anion formation was observed.