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Synthesis and electrochemical study of nitrophenyl derivatives of β ‐cyclodextrin
Author(s) -
Gubica Tomasz,
Stroka Jadwiga,
Temeriusz Andrzej
Publication year - 2007
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.1149
Subject(s) - chemistry , nitrobenzene , nitro , electrochemistry , cyclodextrin , cyclic voltammetry , medicinal chemistry , mercury (programming language) , adsorption , inorganic chemistry , electrode , organic chemistry , catalysis , alkyl , computer science , programming language
A series of nitrophenyl β ‐cyclodextrin derivatives: mono [6‐deoxy‐6‐(4‐nitrobenzamido)]‐ per‐ O‐ methyl‐ β ‐cyclodextrin (R 1 PhNO 2 ), mono [6‐deoxy‐6‐(3‐nitrobenzamido)]‐ per‐O‐ methyl‐ β ‐cyclodextrin (R 2 PhNO 2 ) and heptakis [6‐deoxy‐6‐(4‐nitrobenzamido)‐2,3‐di‐ O‐ methyl]‐ β ‐cyclodextrin [R 3 (PhNO 2 ) 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 NO 2 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 R 3 (PhNO 2 ) 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.