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Record W3012308197 · doi:10.1002/chem.202000384

Zero‐Order Catalysis in TAML‐Catalyzed Oxidation of Imidacloprid, a Neonicotinoid Pesticide

2020· article· en· W3012308197 on OpenAlexaff
Genoa R. Warner, Yogesh Somasundar, Cindy Weng, Mete H. Akin, Alexander D. Ryabov, Terrence J. Collins

Bibliographic record

VenueChemistry - A European Journal · 2020
Typearticle
Languageen
FieldAgricultural and Biological Sciences
TopicInsect and Pesticide Research
Canadian institutionsCegep de Sept Iles
FundersNational Science Foundation
KeywordsImidaclopridCatalysisChemistryMedicinal chemistryAmidePolymer chemistryNuclear chemistryOrganic chemistryPesticide

Abstract

fetched live from OpenAlex

Abstract Bis‐sulfonamide bis‐amide TAML activator [Fe{4‐NO 2 C 6 H 3 ‐1,2‐( N COCMe 2 N SO 2 ) 2 CHMe}] − ( 2 ) catalyzes oxidative degradation of the oxidation‐resistant neonicotinoid insecticide, imidacloprid (IMI), by H 2 O 2 at pH 7 and 25 °C, whereas the tetrakis‐amide TAML [Fe{4‐NO 2 C 6 H 3 ‐1,2‐( N COCMe 2 N CO) 2 CF 2 }] − ( 1 ), previously regarded as the most catalytically active TAML, is inactive under the same conditions. At ultra‐low concentrations of both imidacloprid and 2 , 62 % of the insecticide was oxidized in 2 h, at which time the catalyst is inactivated; oxidation resumes on addition of a succeeding aliquot of 2 . Acetate and oxamate were detected by ion chromatography, suggesting deep oxidation of imidacloprid. Explored at concentrations [ 2 ]≥[IMI], the reaction kinetics revealed unusually low kinetic order in 2 (0.164±0.006), which is observed alongside the first order in imidacloprid and an ascending hyperbolic dependence in [H 2 O 2 ]. Actual independence of the reaction rate on the catalyst concentration is accounted for in terms of a reversible noncovalent binding between a substrate and a catalyst, which usually results in substrate inhibition when [catalyst]≪[substrate] but explains the zero order in the catalyst when [ 2 ]>[IMI]. A plausible mechanism of the TAML‐catalyzed oxidations of imidacloprid is briefly discussed. Similar zero‐order catalysis is presented for the oxidation of 3‐methyl‐4‐nitrophenol by H 2 O 2 , catalyzed by the TAML analogue of 1 without a NO 2 ‐group in the aromatic ring.

Fetched live from OpenAlex and de-inverted. Abstracts are not stored in this database: the inverted indexes are 8.6 GB of the frame’s 9.3 GB of text, and the host has 13 GB free.

How this classification was reachedexpand

Full frame distilled prediction

Teacher imitation

Not calibrated prevalence, not ground truth. Human validation pending. Learned from the 10,348 direct Codex labels and 10,348 direct Gemma labels. Candidate is the union of thresholded teacher heads; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels or direct frontier model labels.

metaresearch head score (Codex)0.001
metaresearch head score (Gemma)0.001
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesInsufficient payload (model declined to judge)
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Bench or experimental · Consensus signal: Bench or experimental
GenreCandidate signal: Empirical · Consensus signal: Empirical
Teacher disagreement score0.165
Threshold uncertainty score0.999

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0010.001
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0000.001
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0000.000
Research integrity0.0000.000
Insufficient payload (model declined to judge)0.0020.000

Machine scores (provisional)

The two teacher heads of the student model, read on this work. A score orders the frame for review; it never asserts a category, and the validation status ships verbatim with every row.

Baseline scores from an immature model (maturity gate not passed, 7 training rounds). Scores rank; they never assert a category.

Opus teacher head0.027
GPT teacher head0.224
Teacher spread0.197 · how far apart the two teachers sit on this one work
Validation statusscore_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from it

Classification

machine, unvalidated

Machine predicted; a candidate call from one teacher head, not a consensus.

Study designBench or experimental
Domainnot available
GenreEmpirical

How this classification was reached, model by model and score by score, is at the end of the page under "How this classification was reached".

Quick stats

Citations14
Published2020
Admission routes1
Has abstractyes

Explore more

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