Stabilization of the pesticide Fenitrothion toward O and N nucleophiles in the presence of cyclodextrins. (24th September 2014)

• Record Type: Journal Article
• Authors: Rougier, Natalia M.; Vico, Raquel V.; de Rossi, Rita H.; Buján, Elba I.
• Is Part Of: Journal of physical organic chemistry. Volume 27:Number 12(2014:Dec.)
• Page Start: 935
• Page End: 943
• Publication Date: 2014-09-24
• Subjects: Chemistry, Physical organic -- Periodicals; 547.1
• DOI: 10.1002/poc.3373
• Languages: English
• ISSNs: 0894-3230

Abstract

<abstract abstract-type="main"> <title> <x xml:space="preserve">Abstract</x> </title> <p>The reaction of Fenitrothion with <italic>O</italic> and <italic>N</italic> nucleophiles (H₂O₂, NH₂OH, <italic>n</italic>‐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 H₂O₂ (81%), which is the most efficient nucleophile in promoting Fenitrothion degradation in homogeneous media. In the absence of CD, competition between the S_N2(P) and the S_N2(C) pathways was observed with piperidine as was reported before for the reaction with NH₂OH and <italic>n</italic>‐butylamine. The presence of β‐CD does not modify product distribution in the case of the reaction with NH₂OH and <italic>n</italic>‐butylamine, whereas there is an increase in S_N2(C) pathway when the nucleophile is piperidine. Copyright © 2014 John Wiley &amp; Sons, Ltd.</p> </abstract>