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<i>N</i> ‐Hydroxyphthalimide

2025· other· en· W4406027795 on OpenAlexaff
Cristian Gambarotti, Carlo Punta, Francesco Recupero, María Zlotorzynska, Glenn M. Sammis, Wade F. Petersen

Bibliographic record

VenueEncyclopedia of Reagents for Organic Synthesis · 2025
Typeother
Languageen
FieldChemistry
TopicOxidative Organic Chemistry Reactions
Canadian institutionsUniversity of British Columbia
Fundersnot available
KeywordsComputer science

Abstract

fetched live from OpenAlex

Abstract image [ 524‐38‐9 ] C 8 H 5 NO 3 (MW 163.11) InChI = 1S/C8H5NO3/c10‐7‐5‐3‐1‐2‐4‐6(5)8(11)9(7)12/h1‐4,12H InChIKey = CFMZSMGAMPBRBE‐UHFFFAOYSA‐N (reagent for the formation of O ‐alkyl hydroxylamines, catalytic precursor to the phthalimido‐ N ‐oxyl radical (PINO), capable of mild and selective abstraction of hydrogen from a wide variety of CH bonds with the formation of free radicals for exploitation in synthetic schemes, oxidation of CH bonds) Physical Data: mp 233 °C; d 1.58 g cm −3 ; refractive index 1.522 (at 589 nm); p K a 6.3 at 25 °C in H 2 O; OH BDE 88 kcal mol −1 ; 1 H NMR (DMSO‐d 6 ) 7.84 (s, 4 H , CH), 10.9 (s, 1 H , OH); 13 C NMR (DMSO‐d 6 ) 168, 134, 128, 123; EPR of the derived radical (PINO) triplet, g = 2.0073, A N = 4.23 G; MASS (EI) ( m/z ) 163 M + , 147, 133, 105, 104, 77, 76, 50. Solubility: 0.33 g L −1 5 °C in benzene; 50.5 g L −1 at 25 °C in H 2 O; soluble in AcOH, CH 3 CN, CH 3 COOEt. Preparative Methods: N ‐hydroxyphthalimide is easily prepared by reaction of phthalic anhydride and hydroxylamine hydrochloride or sulphate in basic conditions. Handling, Storage and Precaution: N ‐hydroxyphthalimide is a white crystalline solid, stable to air, does not need particular precautions for the storage, irritant for the eyes and the skin and very toxic after inhalation.

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 machine prediction

Teacher imitation

Not calibrated prevalence, not ground truth. Human validation pending. The Gemma side is a direct model label for every work in the frame, read from the title-only record. The Codex side is a classifier learned from the 10,348 direct Codex labels and calibrated to design-weighted sample rates; fields without enough sample support carry no Codex call. Candidate is the union of the two sides; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels.

metaresearch head score (Codex)0.000
metaresearch head score (Gemma)0.000
Version: metacan-v3-hybrid-931329e0061cValidation status: machine_predicted_unvalidated
Candidate categoriesnone
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Not applicable · Consensus signal: none
GenreCandidate signal: Other · Consensus signal: Other
Teacher disagreement score0.042
Threshold uncertainty score0.142

Distilled classifier scores by category (both heads)

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0010.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0000.000
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0010.000
Research integrity0.0000.001
Insufficient payload (model declined to judge)0.0420.011

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 head0.008
GPT teacher head0.240
Teacher spread0.232 · 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 source (direct Gemma or distilled Codex), not a consensus.

The models applied no category: nothing in the taxonomy fit this work.
Study designNot applicable
Domainnot available
GenreOther

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".

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Citations0
Published2025
Admission routes1
Has abstractyes

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