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Stabilization of the pesticide Fenitrothion toward O and N nucleophiles in the presence of cyclodextrins
Author(s) -
Rougier Natalia M.,
Vico Raquel V.,
Rossi Rita H.,
Buján Elba I.
Publication year - 2014
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.3373
Subject(s) - chemistry , fenitrothion , piperidine , nucleophile , sn2 reaction , medicinal chemistry , stereochemistry , organic chemistry , pesticide , agronomy , biology , catalysis
The reaction of Fenitrothion with O and N nucleophiles (H 2 O 2 , NH 2 OH, n ‐butylamine and piperidine) was studied at 25 °C in water containing 2% 1,4‐dioxane in the presence of native cyclodextrins (α‐, β‐, and γ‐CD). For all the nucleophiles, the presence of CD produces reaction inhibition with saturation kinetics. The greatest effect in all cases is observed with β‐CD, and the greatest inhibition was observed for the reaction of Fenitrothion with H 2 O 2 (81%), which is the most efficient nucleophile in promoting Fenitrothion degradation in homogeneous media. In the absence of CD, competition between the S N 2(P) and the S N 2(C) pathways was observed with piperidine as was reported before for the reaction with NH 2 OH and n ‐butylamine. The presence of β‐CD does not modify product distribution in the case of the reaction with NH 2 OH and n ‐butylamine, whereas there is an increase in S N 2(C) pathway when the nucleophile is piperidine. Copyright © 2014 John Wiley & Sons, Ltd.