Effect of cyclodextrins on the reactivity of fenitrothion

Rougier, Natalia M.; Cruickshank, Dyanne L.; Vico, Raquel V.; Bourne, Susan A.; Caira, Mino R.; Buján, Elba I.; Rossi, Rita H. de

doi:10.1016/j.carres.2010.06.016

Cited by 17 publications

(32 citation statements)

References 22 publications

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“…This value is similar to that calculated before in the hydrolysis reaction for the association with ionized β-CD, that is, K 2 = 417 ± 118 M À1 . [7] It can be seen that K 1 and K 2 are not significantly different, as previously suggested. [4] The reactions in the presence of α-and γ-CD were performed at only one CD concentration, then no value for K 1 could be calculated but we can assume that they will be comparable to those of K 2 determined previously.…”

Section: Product Analysis Experimentssupporting

confidence: 80%

“…[7] Comparing the inhibition observed with the three CDs, we can see that, as it was the case in the hydrolysis reaction, the inhibition increases with the increase in the association constant of 1 with CDs. [7] Scheme 2. General mechanism for the reaction of Fenitrothion with HOO À in the presence of CDs.…”

Section: Product Analysis Experimentsmentioning

confidence: 80%

“…[6] Previously, we have studied the hydrolysis reactions of 1 in the presence of native (α-, β-, and γ-CD) and methylated CDs, all of them showed inhibition of the reaction with saturation kinetics because of the formation of complexes. [4,7,8] We present now the results on the reaction of 1 with piperidine (Pip) in water and the effects of the presence of native CDs on the reactivity and regiochemistry of the reactions of 1 with H 2 O 2 , NH 2 OH, BuNH 2 , and Pip. As in the reaction of 1 with the other N-based nucleophiles studied, in the reaction with Pip, competition between the S N 2(P) and S N 2(C) pathways was also observed.…”

Section: Fenitrothion [Oo-dimethyl O-(3-methyl-4-nitrophenyl)phosphomentioning

confidence: 98%

“…1, as previously observed in the hydrolysis reaction of 1 in the presence of CDs. [7] The observed rate constant versus β-CD concentration was fitted to an equation of the form of Eqn (1) with a = (2.20 ± 0.08) × 10 À3 , b = (8 ± 1) × 10 À2 , and c = (377 ± 51).…”

Section: Product Analysis Experimentsmentioning

confidence: 99%

“…Reaction pathway d) in Scheme 4 that implies that the aminolysis reaction occurs when the substrate and the amine are complexed each of them with one CD can be discarded on the following bases: (i) crystallographic data, [30] molecular docking calculations [31] and kinetic studies, [7] indicate that Fenitrothion includes in the cavity of one CD, preferably through the thiophosphate group (reaction center); (ii) a second-order dependence on CD concentration, [CD] 2 , is not observed from the plots of k The observed rate constant for the mechanism in Scheme 5 is given by Eqn (17) that has the same mathematical form of Eqn (1) with a and b given by Eqns (18) and (19). In that equation, k A is the sum of k …”

Section: Reaction With Piperidinementioning

confidence: 99%

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Stabilization of the pesticide Fenitrothion towardOandNnucleophiles in the presence of cyclodextrins

Rougier

Vico

Rossi

et al. 2014

J. Phys. Org. Chem.

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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.

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Section: Product Analysis Experimentssupporting

confidence: 80%

Section: Product Analysis Experimentsmentioning

confidence: 80%

Section: Fenitrothion [Oo-dimethyl O-(3-methyl-4-nitrophenyl)phosphomentioning

confidence: 98%

Section: Product Analysis Experimentsmentioning

confidence: 99%

Section: Reaction With Piperidinementioning

confidence: 99%

See 3 more Smart Citations

Stabilization of the pesticide Fenitrothion towardOandNnucleophiles in the presence of cyclodextrins

Rougier

Vico

Rossi

et al. 2014

J. Phys. Org. Chem.

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Supramolecular Chemistry in Solid State Materials such as Metal‐Organic Frameworks

Fracaroli

Rossi

2018

Israel Journal of Chemistry

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Trifluralin and two of its photodegradation products: Crystal structures and phase solubility/UV studies with cyclodextrins

Lobatto

Argüello

Caira

et al. 2019

J of Physical Organic Chem

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The crystal structures of the herbicide trifluralin (1), and two of its photodegradation products, namely, N‐n‐propyl‐2,6‐dinitro‐4‐trifluoromethylaniline (2) and 2‐ethyl‐7‐nitro‐5‐trifluoromethyl‐1H‐benzimidazole 3‐oxide (3), were determined by single‐crystal X‐ray diffraction. The presence of the N‐hydroxy tautomer of 3 was detected in the solid state both by X‐ray diffraction and infrared spectroscopy (IR), while in dimethyl sulfoxide‐d6 ((CD3)2SO) solution, the N‐oxide tautomer was observed by hydrogen‐1 nuclear magnetic resonance (1H NMR). In order to determine whether 1, 2, and 3 form complexes with cyclodextrins in aqueous solutions as well as in the solid state, the interaction of 1 to 3 with β‐cyclodextrin in aqueous solutions containing 1% acetonitrile (ACN) and the interaction of 1 to 3 in the solid state with both native and derivatized cyclodextrins were investigated. In aqueous solutions containing 1% ACN, the association constants for the formation of 1:1 complexes were calculated for 1 and 2 as (25 ± 7) × 101M–1 and (18 ± 2) × 101M–1, respectively, whereas that for 3 could not be determined. Extensive trials aimed at obtaining solid complexes of 1 to 3 with both native and selected crystalline derivatized cyclodextrins using different methods failed to produce inclusion complexes.

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Effect of cyclodextrins on the reactivity of fenitrothion

Cited by 17 publications

References 22 publications

Stabilization of the pesticide Fenitrothion towardOandNnucleophiles in the presence of cyclodextrins

Stabilization of the pesticide Fenitrothion towardOandNnucleophiles in the presence of cyclodextrins

Supramolecular Chemistry in Solid State Materials such as Metal‐Organic Frameworks

Trifluralin and two of its photodegradation products: Crystal structures and phase solubility/UV studies with cyclodextrins

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