HOST-GUEST INTERACTION OF PESTICIDE BIFENOX WITH CYCLODEXTRIN MOLECULES. AN ELECTROCHEMICAL STUDY

0341088 - ÚFCH JH 2010 RIV CZ eng J - Journal Article
Hromadová, Magdaléna - Sokolová, Romana - Pospíšil, Lubomír - Lachmanová, Štěpánka - Fanelli, N. - Giannarelli, S.
HOST-GUEST INTERACTION OF PESTICIDE BIFENOX WITH CYCLODEXTRIN MOLECULES. AN ELECTROCHEMICAL STUDY.
Collection of Czechoslovak Chemical Communications. Roč. 74, 11-12 (2009), s. 1647-1664. ISSN 0010-0765
R&D Projects: GA AV ČR IAA400400802; GA ČR GA203/08/1157; GA ČR GA203/09/0705; GA ČR GA203/09/1607; GA MŠMT LC510; GA MŠMT OC 140
Institutional research plan: CEZ:AV0Z40400503
Keywords : reductions * electroreduction * nitro anion radical * electrochemistry
Subject RIV: CG - Electrochemistry
Impact factor: 0.856, year: 2009

The reduction of nitroaromatic compound bifenox (methyl 5-(2,4-dichlorophenoxy)-2-nitrobenzoate) was studied in aprotic solvents in the absence or presence of cyclodextrin (CD) molecules of different cavity sizes. beta CD and gamma CD form complexes with bifenox in DMSO with the complex formation constants (5 +/- 2) x 10(2) M-1 [beta CD-bifenox] and (3 +/- 1) x 10(2) M-1 [gamma CD -bifenox], respectively. Bifenox yields a relatively stable anion radical in dimethyl sulfoxide, which is further reduced at more negative potentials by an overall addition of three electrons and four protons to the corresponding phenylhydroxylamine. In the presence of beta CD the first reduction wave of bifenox becomes irreversible, it is shifted towards more positive potentials and the uptake of more than one electron is observed (up to four electrons during the exhaustive electrolysis).
Permanent Link: http://hdl.handle.net/11104/0184182